631:
608:
1557:
51:
2406:
1543:
1571:
1515:
1501:
42:
1529:
8992:
3358:
1619:
for apalutamide to the United States Food and Drug
Administration on 11 October 2017. Apalutamide was approved by the Food and Drug Administration in the United States, under the brand name Erleada, for the treatment of non-metastatic castration-resistant prostate cancer in February 2018. It was
3864:
1411:
of apalutamide at steady-state is 3 to 4 days. Fluctuations in apalutamide exposure are low and levels are stable throughout the day, with mean peak-to-trough ratios of 1.63 for apalutamide and 1.27–1.3 for N-desmethylapalutamide. After a single dose of apalutamide, its
3551:
2404:, Jung ME, Sawyers CL, Ouk S, Tran C, Wongvipat J, "Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases", published 8 November 2007, assigned to The Regents Of The University Of California.
2826:
Wu B, Shen P, Yin X, Yu L, Wu F, Chen C, et al. (March 2022). "Analysis of adverse event of interstitial lung disease in men with prostate cancer receiving hormone therapy using the Food and Drug
Administration Adverse Event Reporting System".
2411:
1340:
of apalutamide occur 2 hours following administration, with a range of 1 to 5 hours. Food delays the median time to peak levels of apalutamide by approximately 2 hours, with no significant changes in the peak levels themselves or in
1407:, with similar contribution of each of these enzymes to its formation at steady-state. Following a single oral dose of 200 mg apalutamide, apalutamide represented 45% and N-desmethylapalutamide 44% of total area-under-curve levels. The mean
878:
Apalutamide was first described in 2007, and was approved for the treatment of prostate cancer in
February 2018. It is the first medication to be approved specifically for the treatment of non-metastatic castration-resistant prostate cancer.
3547:
1224:, is not affected by this mutation, nor has it been found to be affected by any other tested/well-known AR mutations. Apalutamide may be effective in a subset of prostate cancer patients with acquired resistance to
709:
2401:
1907:
3430:
A randomized double-blind, comparative study of ARN-509 plus androgen deprivation therapy (ADT) versus ADT alone in nonmetastatic castration-resistant prostate cancer (M0-CRPC): The SPARTAN trial
240:
3494:"TITAN: A randomized, double-blind, placebo-controlled, phase 3 trial of apalutamide (ARN-509) plus androgen deprivation therapy (ADT) in metastatic hormone-sensitive prostate cancer (mHSPC)"
2783:
Kobe H, Tachikawa R, Masuno Y, Matsunashi A, Murata S, Hagimoto H, et al. (September 2021). "Apalutamide-induced severe interstitial lung disease: A report of two cases from Japan".
1135:
may be reduced to varying extents. In terms of effects of other drugs on apalutamide, strong CYP2C8 or CYP3A4 inhibitors may increase levels of apalutamide or its major active metabolite
1615:
clinical studies, including ATLAS, SPARTAN, and TITAN, was published between 2014 and 2016. Positive results for phase III trials were first described in 2017, and
Janssen submitted a
3453:"ATLAS: A phase 3 trial evaluating the efficacy of apalutamide (ARN-509) in patients with high-risk localized or locally advanced prostate cancer receiving primary radiation therapy"
9032:
4796:
8565:
3712:
195:
8359:
7081:
1811:
1220:
The acquired F876L mutation of the AR identified in advanced prostate cancer cells has been found to confer resistance to both enzalutamide and apalutamide. A newer NSAA,
8968:
8011:
7971:
5228:
1353:
for 160 mg/day apalutamide at steady-state are 6.0 μg/mL (12.5 μmol/L), relative to peak levels of 16.6 μg/mL (35.7 μmol/L) for 160 mg/day
3356:, Ouerfelli O, Dilhas A, Yang G, Zhao H, "Synthesis of thiohydantoins", issued 11 June 2013, assigned to Sloan Kettering Institute for Cancer Research.
1604:
that was published in
November 2007 and in another that was submitted in July 2010. A March 2012 publication described the discovery and development of apalutamide. A
891:
for the treatment of people with metastatic castration-sensitive prostate cancer and the treatment of people with non-metastatic castration-resistant prostate cancer.
907:
751:
InChI=1S/C21H15F4N5O2S/c1-27-17(31)13-4-3-11(8-15(13)22)30-19(33)29(18(32)20(30)5-2-6-20)12-7-14(21(23,24)25)16(9-26)28-10-12/h3-4,7-8,10H,2,5-6H2,1H3,(H,27,31)
81:
1897:
2992:"Discovery of ODM-201, a new-generation androgen receptor inhibitor targeting resistance mechanisms to androgen signaling-directed prostate cancer therapies"
723:
8957:
1188:
4789:
4758:
3152:
1214:
1416:
rate (CL/F) was 1.3 L/h, while its clearance rate increased to 2.0 L/h at steady-state. This change is considered to be likely due to CYP3A4
7043:
3705:
2030:
1875:
8021:
7048:
5528:
3548:"Janssen Submits New Drug Application to U.S. FDA for Apalutamide (ARN-509) to Treat Men with Non-Metastatic Castration-Resistant Prostate Cancer"
899:
9037:
7074:
3533:
8329:
7038:
5990:
4782:
4748:
4715:
2881:
1296:
7840:
7033:
5029:
4753:
3698:
9057:
8394:
7845:
5785:
5780:
5378:
4763:
3973:
2187:"Abiraterone and other novel androgen-directed strategies for the treatment of prostate cancer: a new era of hormonal therapies is born"
1342:
8467:
2239:"Targeting the androgen receptor in the management of castration-resistant prostate cancer: rationale, progress, and future directions"
1947:
9087:
8417:
7332:
5218:
2289:
Dellis AE, Papatsoris AG (June 2018). "Apalutamide: The established and emerging roles in the treatment of advanced prostate cancer".
8578:
7357:
2490:"Quo vadis: advanced prostate cancer-clinical care and clinical research in the era of multiple androgen receptor-directed therapies"
8570:
8447:
7067:
5447:
1638:
743:
8655:
7113:
6230:
1593:
8497:
8472:
6629:
5534:
5497:
5292:
5223:
4038:
4018:
2902:"A clinically relevant androgen receptor mutation confers resistance to second-generation antiandrogens enzalutamide and ARN-509"
3738:
1803:
5452:
3993:
3363:
1417:
1346:
414:
380:
225:
113:
3588:
3331:
1682:
8540:
8299:
8001:
4982:
4229:
8477:
6220:
2888:
ARN-509 is related structurally to enzalutamide with greater in vivo activity in CRPC xenograft models (Clegg et al., 2012).
2736:"Interstitial lung disease induced by apalutamide therapy for castration-resistant prostate cancer: A report of a rare case"
1020:. When used as a monotherapy (i.e., without surgical or medical castration) in men, NSAAs are known to produce additional,
8627:
8482:
4889:
4869:
4491:
4303:
1279:
3277:
Liu B, Su L, Geng J, Liu J, Zhao G (2010). "Developments in nonsteroidal antiandrogens targeting the androgen receptor".
2084:
8950:
7028:
6998:
6563:
5857:
5718:
5245:
5071:
4884:
4660:
4252:
2035:
915:
906:
in the treatment of non-metastatic castration-resistant prostate cancer. It is also a promising potential treatment for
903:
527:
8487:
8462:
7371:
1307:= 3.0 and 2.7 μM, respectively), but due to its relatively lower central concentrations, may have a lower risk of
8354:
7890:
7885:
7880:
5935:
5297:
4899:
4732:
4668:
4193:
3947:
3772:
1612:
1605:
1349:
levels of apalutamide are achieved following 4 weeks of administration, with an approximate 5-fold accumulation.
1260:
1198:
1120:
587:
7875:
7870:
5920:
5915:
5723:
1840:
8982:
8264:
6225:
5457:
5076:
4618:
3852:
132:
6567:
9062:
8744:
8734:
8588:
8279:
8160:
7104:
5287:
5108:
5066:
5014:
4960:
4444:
4433:
3827:
3802:
3610:
1941:
1611:
of apalutamide was completed by March 2012, and the results of this study were published in 2013. Information on
1478:
1441:
1072:
774:
188:
8545:
8412:
7327:
7297:
4854:
9077:
9067:
9022:
6730:
5877:
5846:
5566:
5507:
5240:
5018:
4894:
4844:
4023:
3848:
1589:
1413:
1327:
1108:
8492:
6215:
5950:
5930:
5098:
3648:"Profile of apalutamide in the treatment of metastatic castration-resistant prostate cancer: evidence to date"
3145:
8525:
9042:
8739:
8714:
8369:
7172:
6746:
5673:
5417:
5327:
5235:
5135:
5123:
5024:
4720:
4610:
3939:
3894:
3884:
3844:
3832:
3613:(2016). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 75".
1206:
169:
2040:
626:
8135:
7996:
7730:
6738:
6210:
5873:
5512:
5422:
5383:
5255:
5103:
4972:
4921:
4028:
3934:
3840:
3836:
3777:
3381:"Phase I study of ARN-509, a novel antiandrogen, in the treatment of castration-resistant prostate cancer"
1974:"Phase I study of ARN-509, a novel antiandrogen, in the treatment of castration-resistant prostate cancer"
1556:
1377:
1370:
1366:
1195:
1161:
1136:
1060:
1048:
1041:
1033:
576:
359:
317:
8894:
8510:
7162:
2542:
Kawahara T, Miyamoto H (June 2014). "Androgen
Receptor Antagonists in the Treatment of Prostate Cancer".
9027:
9017:
7976:
6270:
5758:
5608:
5502:
5167:
4849:
4652:
4313:
3527:
1865:
1471:
1445:
1408:
1172:
1021:
7775:
2031:"FDA approves new treatment for a certain type of prostate cancer using novel clinical trial endpoint"
1194:, but shows some advantages, including higher antiandrogenic activity as well as several-fold reduced
8699:
8364:
8219:
7855:
7366:
7167:
6544:
6430:
5898:
5869:
5842:
5708:
5596:
5405:
5373:
5339:
5061:
4977:
4948:
4664:
4472:
4363:
3958:
3943:
3919:
3812:
3797:
3233:
3096:
Ivachtchenko AV, Mitkin OD, Kudan EV, Rjahovsky AA, Vorobiev AA, Trifelenkov AS, et al. (2014).
3003:
1616:
1597:
371:
7705:
603:
9012:
8749:
8729:
8224:
8213:
7850:
7554:
7376:
7267:
6953:
6948:
6680:
6640:
6485:
6405:
6305:
6295:
6240:
5820:
5356:
5113:
4967:
4864:
4697:
4656:
4560:
4506:
4488:
4348:
4323:
4318:
4300:
4289:
4243:
3963:
1542:
1350:
1337:
1330:
1225:
1158:
961:
918:
864:
844:
786:
435:
176:
6116:
6106:
9082:
9072:
8929:
7938:
7610:
7572:
7227:
7217:
7096:
6549:
5790:
5653:
5613:
5591:
5524:
5427:
5400:
5368:
5201:
5091:
4943:
4808:
4602:
4564:
4033:
3968:
3924:
3914:
3889:
3817:
3792:
3302:
3202:
2852:
2808:
2716:
2519:
2314:
2156:
1601:
1180:
989:
965:
820:
143:
8031:
7795:
6590:
6585:
6370:
6146:
6136:
2638:"Beyond abiraterone: new hormonal therapies for metastatic castration-resistant prostate cancer"
1139:, while mild to moderate CYP2C8 or CYP3A4 inhibitors are not expected to affect their exposure.
8889:
8884:
8879:
8874:
8869:
8834:
8505:
8249:
6889:
6824:
6819:
6769:
6600:
6514:
6126:
3049:"ODM-201: a new-generation androgen receptor inhibitor in castration-resistant prostate cancer"
9052:
8859:
8844:
8719:
8560:
8555:
8530:
8289:
8191:
8125:
7820:
7582:
7429:
7384:
7222:
7207:
7202:
7177:
6884:
6804:
6759:
6710:
6534:
6519:
6450:
6420:
6380:
6245:
6161:
6071:
6021:
5940:
5743:
5648:
5467:
5184:
5046:
4955:
4938:
4906:
4859:
4816:
4805:
4672:
4496:
4353:
4343:
4281:
3787:
3753:
3679:
3515:
3474:
3410:
3294:
3259:
3194:
3127:
3078:
3029:
2972:
2923:
2877:
2871:
2844:
2800:
2765:
2708:
2667:
2615:
2559:
2511:
2467:
2380:
2306:
2268:
2216:
2148:
2003:
1451:
1400:
1168:
1164:
1025:
969:
852:
848:
796:
782:
516:
277:
264:
252:
63:
8041:
7800:
6350:
6345:
6335:
6176:
6006:
451:
9047:
8849:
8684:
8437:
8095:
7895:
7825:
7660:
7558:
7390:
7271:
6879:
6700:
6690:
6670:
6051:
5955:
5618:
5482:
5041:
4879:
4839:
4614:
4545:
3868:
3669:
3659:
3622:
3505:
3492:
Chi K, Chowdhury S, Radziszewski P, Lebret T, Ozguroglu M, Sternberg C, et al. (2016).
3464:
3433:
3400:
3392:
3379:
Rathkopf DE, Morris MJ, Fox JJ, Danila DC, Slovin SF, Hager JH, et al. (October 2013).
3286:
3249:
3241:
3186:
3117:
3109:
3068:
3060:
3019:
3011:
2962:
2954:
2913:
2836:
2792:
2755:
2747:
2698:
2657:
2649:
2605:
2595:
2551:
2501:
2457:
2449:
2370:
2362:
2298:
2258:
2250:
2206:
2198:
2140:
1993:
1985:
1972:
Rathkopf DE, Morris MJ, Fox JJ, Danila DC, Slovin SF, Hager JH, et al. (October 2013).
1936:
1570:
1428:(1.2% as unchanged apalutamide and 2.7% as N-desmethylapalutamide) while 24% is excreted in
1104:
1017:
929:
836:
643:
444:
299:
3222:"Development of a second-generation antiandrogen for treatment of advanced prostate cancer"
2990:
Moilanen AM, Riikonen R, Oksala R, Ravanti L, Aho E, Wohlfahrt G, et al. (July 2015).
536:
50:
8996:
8196:
8105:
8070:
7738:
7720:
7645:
7602:
7465:
6615:
6500:
6355:
6041:
6026:
5693:
5668:
5519:
5472:
5282:
5142:
4638:
4203:
4113:
3998:
3367:
2900:
Joseph JD, Lu N, Qian J, Sensintaffar J, Shao G, Brigham D, et al. (September 2013).
2415:
1657:
Apalutamide is available in the United States, Canada, the
European Union, and Australia.
1514:
1333:
1241:
778:
630:
607:
332:
307:
3437:
3237:
3007:
1500:
8779:
8674:
7724:
7594:
7586:
7489:
7415:
7380:
6460:
6285:
6260:
5888:
5864:
5837:
5800:
5733:
5658:
5561:
5346:
5317:
5174:
5117:
5056:
5051:
4726:
4622:
4584:
4572:
4531:
4368:
4177:
4169:
4161:
4133:
4118:
4063:
3879:
3674:
3451:
Bossi A, Dearnaley D, McKenzie M, Baskin-Bey E, Tyler R, Tombal B, et al. (2016).
3405:
3380:
3254:
3221:
3122:
3098:"Preclinical Development of ONC1-13B, Novel Antiandrogen for Prostate Cancer Treatment"
3097:
3073:
3048:
3024:
2991:
2967:
2942:
2760:
2735:
2662:
2637:
2610:
2462:
2437:
2375:
2350:
2263:
2238:
2211:
2186:
1998:
1973:
1898:"Drug and medical device highlights 2018: Helping you maintain and improve your health"
1608:
1283:
1264:
1237:
1124:
1064:
997:
977:
953:
872:
828:
804:
9006:
8689:
8379:
8186:
8074:
8055:
7991:
7918:
7830:
7780:
7746:
7709:
7670:
7620:
7460:
7455:
7445:
7409:
7312:
7247:
7197:
7146:
7090:
6869:
6814:
6789:
6365:
5763:
5663:
4874:
4103:
3190:
2856:
2812:
2703:
2686:
2349:
Clegg NJ, Wongvipat J, Joseph JD, Tran C, Ouk S, Dilhas A, et al. (March 2012).
1902:
1870:
1528:
993:
824:
619:
476:
105:
3353:
3306:
3206:
2318:
8646:
8617:
8611:
8422:
8209:
8172:
8168:
8090:
7986:
7674:
7649:
7625:
7347:
7152:
7008:
6864:
6794:
6695:
6685:
6650:
6620:
6554:
6529:
6480:
6435:
6400:
6375:
6320:
6275:
6111:
5893:
5810:
5698:
5628:
5603:
5551:
5541:
5487:
5334:
5267:
5152:
5147:
5130:
5081:
4628:
4516:
4423:
4408:
4398:
4393:
4383:
4338:
4333:
4272:
4239:
4225:
4211:
4123:
4088:
4053:
4043:
4008:
3953:
3904:
3899:
3725:
3580:
2720:
2523:
2160:
1674:
1634:
1548:
1455:
1362:
1354:
1314:
Apalutamide has been found to significantly and concentration-dependently increase
1221:
1210:
1191:
1184:
1176:
1056:
1044:
1029:
1009:
949:
911:
860:
840:
812:
208:
203:
91:
3323:
3064:
2584:"Emerging molecularly targeted therapies in castration refractory prostate cancer"
2366:
2302:
2958:
2918:
2901:
2796:
2555:
2453:
8899:
8824:
8759:
8598:
8535:
8442:
8384:
8294:
8155:
8115:
7910:
7770:
7765:
7754:
7750:
7700:
7690:
7577:
7562:
7544:
7439:
7405:
7262:
7212:
7192:
7142:
6993:
6874:
6859:
6854:
6784:
6720:
6675:
6579:
6575:
6571:
6470:
6465:
6445:
6385:
6330:
6300:
6290:
6280:
6250:
6235:
6151:
6131:
6036:
5960:
5852:
5805:
5770:
5688:
5678:
5623:
5581:
5546:
5492:
5477:
5442:
5437:
5191:
5162:
4648:
4632:
4580:
4576:
4568:
4553:
4526:
4467:
4462:
4457:
4452:
4418:
4233:
4173:
4157:
4083:
4078:
4048:
4013:
4003:
3988:
3983:
3909:
3856:
1361:)-bicalutamide levels of 21.6 μg/mL (50.2 μmol/L) for 150 mg/day
1315:
1091:
of apalutamide. General supportive measures should be undertaken until clinical
1068:
957:
895:
792:
99:
4774:
3510:
3493:
3469:
3452:
3177:
Cockshott ID (2004). "Bicalutamide: clinical pharmacokinetics and metabolism".
8784:
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8603:
8593:
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8269:
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8234:
8201:
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7961:
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7922:
7914:
7815:
7810:
7805:
7790:
7742:
7715:
7680:
7655:
7514:
7509:
7503:
7450:
7399:
7395:
7282:
7137:
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6930:
6779:
6774:
6754:
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6645:
6610:
6605:
6595:
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6425:
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6310:
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5975:
5883:
5832:
5683:
5633:
5586:
5576:
5395:
5363:
5322:
5272:
5262:
5208:
5196:
5157:
5009:
5004:
4999:
4994:
4989:
4911:
4642:
4598:
4521:
4501:
4413:
4388:
4358:
4165:
4148:
4108:
4093:
4073:
3822:
3807:
3690:
2144:
2076:
1520:
1482:
1384:
1374:
685:
507:
353:
183:
3519:
3478:
3396:
2563:
2202:
1989:
1641:. It is also known by its developmental code names ARN-509 and JNJ-56021927.
8919:
8914:
8904:
8864:
8809:
8794:
8774:
8769:
8754:
8550:
8520:
8427:
8407:
8402:
8254:
8176:
8110:
8080:
8051:
7981:
7966:
7933:
7900:
7664:
7640:
7598:
7590:
7549:
7539:
7523:
7519:
7495:
7480:
7475:
7435:
7352:
7337:
7302:
7292:
7277:
7252:
7232:
7187:
6984:
6958:
6938:
6934:
6922:
6799:
6764:
6705:
6665:
6660:
6559:
6539:
6475:
6440:
6415:
6410:
6395:
6315:
6265:
6186:
6121:
6066:
6056:
6046:
5980:
5827:
5815:
5571:
5462:
5390:
5351:
5277:
5250:
5179:
4933:
4916:
4606:
4588:
4511:
4403:
4328:
4308:
4219:
4215:
4153:
4068:
3782:
3245:
1506:
1486:
1421:
1052:
1037:
1013:
1005:
933:
888:
388:
85:
33:
7059:
3683:
3414:
3298:
3290:
3263:
3198:
3131:
3082:
3033:
2976:
2927:
2848:
2804:
2769:
2712:
2671:
2619:
2515:
2471:
2384:
2310:
2272:
2220:
2152:
2007:
3974:
Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)
2943:"Resistance emerges to second-generation antiandrogens in prostate cancer"
2687:"The role of antiandrogen monotherapy in the treatment of prostate cancer"
2600:
2583:
1833:
8909:
8839:
8829:
8789:
8764:
8704:
8607:
8515:
8389:
8319:
8274:
8205:
8145:
8130:
8045:
8006:
7905:
7785:
7694:
7634:
7614:
7606:
7499:
7485:
7469:
7419:
7317:
7307:
7287:
7257:
7241:
7132:
6970:
6849:
6844:
6839:
6834:
6829:
6635:
6390:
6325:
6141:
6096:
6091:
6086:
6081:
6076:
6031:
5970:
5965:
5905:
5086:
4928:
4692:
4594:
4183:
3860:
3733:
3721:
3220:
Tran C, Ouk S, Clegg NJ, Chen Y, Watson PA, Arora V, et al. (2009).
2582:
Patel JC, Maughan BL, Agarwal AM, Batten JA, Zhang TY, Agarwal N (2013).
1534:
1474:
1463:
1291:
1092:
1088:
1084:
1075:
with apalutamide exist similarly to with first-generation NSAAs however.
981:
856:
808:
487:
127:
3664:
3647:
3627:
496:
41:
8814:
8799:
8709:
8622:
8349:
8309:
8304:
8229:
8140:
8120:
8036:
7865:
7860:
7685:
7425:
7341:
7322:
7157:
6926:
6715:
6655:
6455:
6340:
6181:
6156:
6011:
5753:
5703:
5643:
5304:
4143:
3761:
2751:
2506:
2489:
2438:"Androgen receptor antagonists in castration-resistant prostate cancer"
2254:
1308:
1272:
1252:
1202:
1132:
1112:
1001:
937:
868:
832:
731:
CNC(=O)C1=C(C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CN=C(C(=C4)C(F)(F)F)C#N)F
462:
17:
3428:
Smith MR, Liu G, Shreeve SM, Matheny S, Sosa A, Kheoh TS, et al.
3015:
2840:
2653:
1205:
and other central side effects. Apalutamide has 5- to 10-fold greater
8679:
7630:
7533:
7237:
6977:
6918:
6903:
6809:
3113:
1562:
1467:
1459:
1404:
1396:
1392:
1256:
1248:
1244:
1116:
1107:. In terms of effects of apalutamide on other drugs, the exposure of
973:
800:
567:
345:
341:
1620:
subsequently approved in Canada, the
European Union, and Australia.
1649:
Apalutamide is marketed under the brand names
Erleada and Erlyand.
556:
8724:
8374:
8100:
7950:
7566:
7182:
6509:
6191:
6101:
1432:(1.5% as unchanged apalutamide and 2% as N-desmethylapalutamide).
1429:
1425:
1388:
1268:
1128:
708:
699:
398:
393:
337:
2131:
Al-Salama ZT (April 2018). "Apalutamide: First Global
Approval".
8819:
8632:
8314:
8284:
8026:
8016:
7956:
7946:
7942:
7529:
6942:
6255:
2873:
Pharmacology and Therapeutics of Constitutively Active Receptors
1369:
of apalutamide at steady-state is approximately 276 L. The
985:
816:
547:
283:
258:
7063:
4778:
3694:
894:
Apalutamide is used in conjunction with castration, either via
271:
122:
7734:
6625:
1600:. It was first described in the literature in a United States
6032:
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
5991:
4875:
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
2351:"ARN-509: a novel antiandrogen for prostate cancer treatment"
1297:
2077:"FDA Approves Apalutamide for Nonmetastatic Prostate Cancer"
1834:"Product monograph including patient medication information"
592:
422:
4--8-oxo-6-sulfanylidene-5,7-diazaspirooctan-5-yl]-2-fluoro-
1201:. The latter difference may reduce its comparative risk of
234:
154:
8330:
5716:
17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:
247:
5219:
7α-Methyl-19-norandrostenedione (MENT dione, trestione)
2537:
2535:
2533:
1493:
Chemical structures of apalutamide and its predecessors
1446:
List of antiandrogens § Nonsteroidal antiandrogens
8656:
7114:
5913:
5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:
8980:
1247:
similarly to enzalutamide. It is a strong inducer of
6999:
4253:
3880:
Androstanolone (stanolone, dihydrotestosterone, DHT)
2544:
Clinical Immunology, Endocrine & Metabolic Drugs
1967:
1965:
1798:
1796:
1794:
1792:
1790:
1788:
1786:
1784:
1782:
1780:
1778:
1776:
1774:
1772:
1770:
1768:
1766:
1764:
1762:
1760:
1758:
1756:
1754:
1752:
1750:
1748:
1746:
1744:
1742:
1740:
1738:
1736:
1734:
1732:
1730:
1728:
1726:
1724:
1722:
1720:
1004:(in 0.2%), among others. Apalutamide is an expected
8654:
8645:
8328:
7112:
7103:
6911:
6902:
6200:
5989:
5347:
Normethandrone (methylestrenolone, normethisterone)
4829:
4815:
4682:
4544:
4481:
4443:
4432:
4280:
4271:
4202:
4119:
Normethandrone (methylestrenolone, normethisterone)
3895:
Drostanolone propionate (dromostanolone propionate)
3752:
3739:
3732:
2734:Kirishima F, Shigematsu Y, Kobayashi K (May 2022).
1718:
1716:
1714:
1712:
1710:
1708:
1706:
1704:
1702:
1700:
697:
684:
642:
637:
618:
586:
566:
546:
526:
506:
486:
461:
434:
405:
387:
370:
352:
331:
316:
306:
298:
224:
219:
194:
182:
168:
142:
112:
98:
80:
72:
62:
57:
5559:17α-Alkylated 5α-dihydrotestosterone derivatives:
3047:Fizazi K, Albiges L, Loriot Y, Massard C (2015).
4009:Metandienone (methandienone, methandrostenolone)
3324:"Apalutamide - Janssen Research and Development"
2941:Nelson WG, Yegnasubramanian S (September 2013).
2126:
2124:
2122:
1470:. Enzalutamide and RD-162 were derived from the
867:. In doing so, it prevents the effects of these
795:of apalutamide when added to castration include
475:
5778:5α-Dihydro-17α-ethynyltestosterone derivatives:
2631:
2629:
2577:
2575:
2573:
2431:
2429:
2427:
2425:
2423:
2396:
2394:
2344:
2342:
2340:
2338:
2336:
2334:
2332:
2330:
2328:
2284:
2282:
2232:
2230:
2180:
2178:
2176:
2174:
2172:
2170:
2120:
2118:
2116:
2114:
2112:
2110:
2108:
2106:
2104:
2102:
1373:of apalutamide is 96%, while that of its major
908:metastatic castration-resistant prostate cancer
450:
443:
5229:11β-Methyl-19-nortestosterone dodecylcarbonate
4061:17α-Alkylated dihydrotestosterone derivatives:
3318:
3316:
2483:
2481:
2070:
2068:
2066:
2064:
2062:
2060:
2058:
2039:(Press release). 24 March 2020. Archived from
1931:
1929:
1927:
1925:
360:
324:
9033:GABAA receptor negative allosteric modulators
7075:
5996:Tooltip Selective androgen receptor modulator
5641:17α-Alkylated 19-nortestosterone derivatives:
4790:
4101:17α-Alkylated 19-nortestosterone derivatives:
3706:
2237:Leibowitz-Amit R, Joshua AM (December 2012).
1403:, N-desmethylapalutamide, is formed by these
1305:Tooltip half-maximal inhibitory concentration
8:
6047:Enobosarm (ostarine, MK-2866, GTx-024, S-22)
3920:Metenolone enanthate (methenolone enanthate)
3575:
3573:
3571:
3569:
2185:Schweizer MT, Antonarakis ES (August 2012).
1675:"Apalutamide (Erleada) Use During Pregnancy"
1380:is 95%, both irrespective of concentration.
1263:. In addition, apalutamide is an inducer of
777:(NSAA) medication used for the treatment of
131:
32:
7091:
5798:17α-Ethynyl-19-nortestosterone derivatives:
4244:
291:In general: ℞ (Prescription only)
8651:
8339:Tooltip γ-Aminobutyric acid A-rho receptor
7109:
7082:
7068:
7060:
6908:
5520:Methylclostebol (chloromethyltestosterone)
5415:5α-Dihydro-19-nortestosterone derivatives:
4826:
4797:
4783:
4775:
4440:
4277:
3749:
3713:
3699:
3691:
1804:"Erleada- apalutamide tablet, film coated"
835:. The medication has a high potential for
629:
606:
515:
5741:17α-Vinyl-19-nortestosterone derivatives:
5357:Oxabolone cipionate (oxabolone cypionate)
4973:DHEA (androstenolone, prasterone; 5-DHEA)
4817:
4282:
3964:Oxabolone cipionate (oxabolone cypionate)
3808:Prasterone (dehydroepiandrosterone, DHEA)
3754:
3673:
3663:
3626:
3581:"Apalutamide Monograph for Professionals"
3509:
3468:
3404:
3253:
3121:
3072:
3023:
2966:
2917:
2759:
2702:
2661:
2609:
2599:
2505:
2461:
2374:
2262:
2210:
2025:
2023:
2021:
2019:
2017:
1997:
1866:"Regulatory Decision Summary for Erleada"
1067:have not been reported with apalutamide.
1012:in male infants if taken by women during
535:
5448:Chlorodehydromethylandrostenediol (CDMA)
3915:Metenolone acetate (methenolone acetate)
902:(GnRH analogue) therapy, as a method of
8987:
7049:List of androgens and anabolic steroids
5435:17α-Alkylated testosterone derivatives:
3981:17α-Alkylated testosterone derivatives:
1666:
1496:
900:gonadotropin-releasing hormone analogue
748:
728:
602:
495:
419:
104:
8664:Tooltip γ-Aminobutyric acid B receptor
7122:Tooltip γ-Aminobutyric acid A receptor
5453:Chlorodehydromethyltestosterone (CDMT)
5209:Testifenon (testiphenon, testiphenone)
3994:Chlorodehydromethyltestosterone (CDMT)
3525:
1592:system and was developed primarily by
1420:. Approximately 65% of apalutamide is
936:and a history of or susceptibility to
620:
31:
5734:Norvinisterone (vinylnortestosterone)
5268:Bolmantalate (nandrolone adamantoate)
5263:Bolandione (19-nor-4-androstenedione)
4978:DHEA enanthate (prasterone enanthate)
4134:Norvinisterone (vinylnortestosterone)
3813:Prasterone enanthate (DHEA enanthate)
3591:from the original on 10 December 2022
3554:from the original on 15 February 2018
3146:"Reference at www.accessdata.fda.gov"
2087:from the original on 24 November 2020
1950:from the original on 28 December 2020
1685:from the original on 29 November 2020
1103:Apalutamide has a high potential for
575:
90:
7:
8969:GABA metabolism/transport modulators
7004:Tooltip Sex hormone-binding globulin
5751:17α-Ethynyltestosterone derivatives:
5030:Polytestosterone phloretin phosphate
4258:Tooltip human chorionic gonadotropin
4141:17α-Ethynyltestosterone derivatives:
3438:10.1200/jco.2014.32.15_suppl.tps5100
1846:from the original on 3 November 2022
1814:from the original on 9 November 2020
1477:, which itself was derived from the
207:
7365:Positive modulators (abridged; see
5674:Methylhydroxynandrolone (MOHN, MHN)
5379:Trenbolone hexahydrobenzylcarbonate
5039:5α-Dihydrotestosterone derivatives:
4907:Androstenedione (4-androstenedione)
4764:List of androgens/anabolic steroids
3744:Tooltip anabolic–androgenic steroid
3334:from the original on 3 January 2019
3158:from the original on 27 August 2021
3053:Expert Review of Anticancer Therapy
2876:. Elsevier Science. pp. 351–.
984:. Other side effects have included
555:
466:
76:ARN-509; JNJ-56021927; JNJ-927; A52
5731:17α-Vinyltestosterone derivatives:
5493:Methandriol (methylandrostenediol)
4693:Androvax (androstenedione albumin)
4131:17α-Vinyltestosterone derivatives:
4014:Methandriol (methylandrostenediol)
3532:: CS1 maint: overridden setting (
3330:. Springer Nature Switzerland AG.
1910:from the original on 17 April 2024
1594:Janssen Research & Development
1588:Apalutamide was originated by the
1095:, if any, diminishes or resolves.
25:
8900:Homotaurine (tramiprosate, 3-APS)
8398:-Chloroacetylcytosine arabinoside
7193:Homotaurine (tramiprosate, 3-APS)
5771:Ethisterone (ethynyltestosterone)
5488:Metandienone (methandrostenolone)
5318:Methoxydienone (methoxygonadiene)
4929:Boldione (1,4-androstadienedione)
4880:Androstenediol (5-androstenediol)
4845:4-Dehydroepiandrosterone (4-DHEA)
4759:Progestogens and antiprogestogens
4158:ethisterone (ethynyltestosterone)
3818:Prasterone sulfate (DHEA sulfate)
3646:Chong JT, Oh WK, Liaw BC (2018).
1878:from the original on 2 April 2024
1639:international nonproprietary name
1040:levels. Similarly to the related
948:Apalutamide has been found to be
8990:
7044:Progesterone receptor modulators
5535:Methyltestosterone 3-hexyl ether
5498:Methandriol bisenanthoyl acetate
5458:Chloromethylandrostenediol (CMA)
5293:Dimethandrolone dodecylcarbonate
5052:1-Androsterone (1-andro, 1-DHEA)
4039:Methyltestosterone 3-hexyl ether
4019:Methandriol bisenanthoyl acetate
3877:Dihydrotestosterone derivatives:
3191:10.2165/00003088-200443130-00003
2704:10.1046/j.1464-410x.2003.04026.x
2488:Kim W, Ryan CJ (February 2015).
1569:
1555:
1541:
1527:
1513:
1499:
1278:Apalutamide binds weakly to and
666:
660:
654:
49:
40:
8192:Pentylenetetrazol (pentetrazol)
5216:19-Nortestosterone derivatives:
3932:19-Nortestosterone derivatives:
2191:Therapeutic Advances in Urology
756:Key:HJBWBFZLDZWPHF-UHFFFAOYSA-N
6231:15β-Hydroxycyproterone acetate
6122:OPK-88004 (LY-2452473, TT-701)
4698:Ovandrotone albumin (Fecundin)
4170:norethisterone (norethindrone)
2075:Mulcahy N (14 February 2018).
1008:and has a theoretical risk of
678:
672:
648:
365:Tooltip N-Desmethylapalutamide
1:
9038:Hormonal antineoplastic drugs
8951:Receptor/signaling modulators
8106:Isopregnanolone (sepranolone)
7029:Receptor/signaling modulators
5786:17α-Ethynyl-3β-androstanediol
5781:17α-Ethynyl-3α-androstanediol
5224:11β-Methyl-19-nortestosterone
3065:10.1586/14737140.2015.1081566
2436:Rathkopf D, Scher HI (2013).
2367:10.1158/0008-5472.CAN-11-3948
2303:10.1080/13543784.2018.1484107
1637:of the medication and is its
1336:of apalutamide is 100%. Mean
8962:receptor positive modulators
7470:ergoloid (dihydroergotoxine)
7039:Estrogen receptor modulators
6486:Trimethyltrienolone (R-2956)
5858:Lynestrenol phenylpropionate
5246:19-Nordehydroepiandrosterone
4749:Androgen receptor modulators
4661:hydroxyprogesterone caproate
4124:Propetandrol (propethandrol)
4054:Tiomesterone (thiomesterone)
3432:. 2014 ASCO Annual Meeting.
3385:Journal of Clinical Oncology
2959:10.1158/2159-8290.CD-13-0405
2919:10.1158/2159-8290.CD-13-0226
2797:10.1016/j.resinv.2021.05.006
2642:Cancer Biology & Therapy
2556:10.2174/22127070114019990002
2454:10.1097/PPO.0b013e318282635a
2036:Food and Drug Administration
1978:Journal of Clinical Oncology
1839:. Janssen Inc. 6 July 2021.
916:androgen synthesis inhibitor
904:androgen deprivation therapy
769:, sold under the brand name
7034:Androgens and antiandrogens
6805:Ralaniten acetate (EPI-506)
6221:7α-Thiomethylspironolactone
5936:Medroxyprogesterone acetate
5298:Dimethandrolone undecanoate
5109:Dihydromethylandrostenediol
4900:Androstenediol dipropionate
4754:Estrogens and antiestrogens
4690:Androstenedione immunogens:
4669:medroxyprogesterone acetate
4249:Tooltip luteinizing hormone
4194:Medroxyprogesterone acetate
3948:nandrolone phenylpropionate
3853:testosterone ester mixtures
3773:Androstenediol dipropionate
1295:similarly to enzalutamide (
1261:UDP-glucuronosyltransferase
1259:, as well as an inducer of
1121:UDP-glucuronosyltransferase
875:and elsewhere in the body.
9104:
9058:Nonsteroidal antiandrogens
8161:Nonsteroidal antiandrogens
5124:Dihydrotestosterone esters
5077:11-Ketodihydrotestosterone
4890:Androstenediol 17β-acetate
4870:11β-Hydroxyandrostenedione
4855:4,17α-Dimethyltestosterone
4619:ethinylestradiol sulfonate
3550:(Press release). Janssen.
2291:Expert Opin Investig Drugs
1439:
638:Chemical and physical data
379:Apalutamide: 3–4 days (at
9088:Trifluoromethyl compounds
8942:
7021:
5928:Progesterone derivatives:
5719:5α-Dihydronorethandrolone
5288:Dimethandrolone buciclate
5118:androstanolone, stanolone
5114:Dihydrotestosterone (DHT)
5072:7β-Hydroxyepiandrosterone
4961:Cloxotestosterone acetate
4885:Androstenediol 3β-acetate
4837:Testosterone derivatives:
4822:Tooltip Androgen receptor
4710:
4287:Tooltip Androgen receptor
4191:Progesterone derivatives:
3803:Cloxotestosterone acetate
3770:Testosterone derivatives:
3759:Tooltip Androgen receptor
3611:World Health Organization
2685:Anderson J (March 2003).
2636:Pinto Á (February 2014).
2145:10.1007/s40265-018-0900-z
1942:European Medicines Agency
1442:Nonsteroidal antiandrogen
1236:Apalutamide shows potent
1073:interstitial lung disease
1036:in general by increasing
775:nonsteroidal antiandrogen
739:
719:
410:
189:Nonsteroidal antiandrogen
48:
39:
7710:sulfonmethane (sulfonal)
6734:-Butylbenzenesulfonamide
5921:5α-Dihydronorethisterone
5916:5α-Dihydrolevonorgestrel
5878:norethisterone enanthate
5847:levonorgestrel butanoate
5724:5α-Dihydronormethandrone
5577:Mebolazine (dimethazine)
5567:Desoxymethyltestosterone
5508:Methandriol dipropionate
5305:LS-1727 (nandrolone 17β-
5241:19-Nor-5-androstenedione
5099:Dihydroethyltestosterone
4895:Androstenediol diacetate
4074:Mebolazine (dimethazine)
4024:Methandriol dipropionate
3849:testosterone undecanoate
3562:– via PR Newswire.
3511:10.1093/annonc/mdw372.54
3470:10.1093/annonc/mdw372.52
3397:10.1200/JCO.2013.50.1684
2203:10.1177/1756287212452196
1990:10.1200/JCO.2013.50.1684
1590:University of California
910:(mCRPC), which the NSAA
6865:Topilutamide (fluridil)
6226:11α-Hydroxyprogesterone
5236:19-Nor-5-androstenediol
5136:Drostanolone propionate
4424:Topilutamide (fluridil)
3845:testosterone propionate
3366:5 November 2021 at the
3246:10.1126/science.1168175
2870:Tao YX (11 June 2014).
2414:4 November 2021 at the
1153:Antiandrogenic activity
960:reported when added to
956:, with the most common
932:of apalutamide include
831:. Rarely, it can cause
785:inhibitor. It is taken
8589:5α-Dihydroprogesterone
8136:Morphine-3-glucuronide
7796:Hyenachin (mellitoxin)
7681:Retigabine (ezogabine)
6750:-Desmethylenzalutamide
6456:SC-5233 (spirolactone)
5874:norethisterone acetate
5513:Methandriol propionate
5384:Trenbolone undecanoate
5256:Bolandiol dipropionate
5104:Dihydrofluoxymesterone
5067:5α-Androst-2-en-17-one
4922:Boldenone undecylenate
4029:Methandriol propionate
3935:Bolandiol dipropionate
3841:testosterone enanthate
3837:testosterone cypionate
3778:Boldenone undecylenate
3291:10.1002/cmdc.201000259
1485:and by extension from
1378:N-desmethylapalutamide
1371:plasma protein binding
1367:volume of distribution
1255:and a weak inducer of
1196:central nervous system
1189:second-generation NSAA
1157:Apalutamide acts as a
1137:N-desmethylapalutamide
1061:elevated liver enzymes
1049:first-generation NSAAs
1042:second-generation NSAA
7977:Chlorophenylsilatrane
6742:-Desmethylapalutamide
6271:Chlormadinone acetate
6216:7α-Thiospironolactone
6087:LGD-2941 (LGD-122941)
6077:LG121071 (LGD-121071)
5951:3-Keto-5α-abiraterone
5931:6α-Methylprogesterone
5870:Norethisterone esters
5843:Levonorgestrel esters
5759:Ethinylandrostenediol
5609:Methyl-1-testosterone
5529:+esterified estrogens
5503:Methandriol diacetate
5168:Mesterolone cipionate
4850:4-Hydroxytestosterone
4653:chlormadinone acetate
4314:Chlormadinone acetate
3885:Androstanolone esters
1598:Johnson & Johnson
1472:nonsteroidal androgen
1409:elimination half-life
1215:first-generation NSAA
1179:. It is similar both
1173:ligand-binding domain
1018:impair male fertility
896:bilateral orchiectomy
8927:Negative modulators:
8807:Positive modulators:
8700:Arbaclofen placarbil
8586:Negative modulators:
8435:Positive modulators:
8220:Pregnenolone sulfate
7856:17-Phenylandrostenol
7838:Negative modulators:
7723:constituents (e.g.,
7693:constituents (e.g.,
7555:Neuroactive steroids
7532:constituents (e.g.,
7268:Neuroactive steroids
6431:Potassium canrenoate
5899:Quingestanol acetate
5709:Tetrahydrogestrinone
5597:Metenolone enanthate
5423:5α-Dihydrotrestolone
5418:5α-Dihydronandrolone
5406:Trestolone enanthate
5374:Trenbolone enanthate
5340:Norclostebol acetate
4949:Clostebol propionate
4665:gestonorone caproate
4473:Saw palmetto extract
4364:Potassium canrenoate
3959:Norclostebol acetate
3944:nandrolone decanoate
3798:Clostebol propionate
3615:WHO Drug Information
1946:. 13 November 2018.
1617:New Drug Application
839:. Apalutamide is an
8516:Gabazine (SR-95531)
8506:CGP-36742 (SGS-742)
8214:dihydropicrotoxinin
7939:Bicyclic phosphates
7851:11-Ketoprogesterone
7786:Gabazine (SR-95531)
7611:pyrazolopyrimidines
6954:Dihydrotestosterone
6949:Dehydroandrosterone
6800:Ralaniten (EPI-002)
6681:Inocoterone acetate
6406:Nomegestrol acetate
6306:Delmadinone acetate
6296:Cyproterone acetate
6241:Abiraterone acetate
6211:7α-Thioprogesterone
5821:Etynodiol diacetate
5025:Testosterone esters
4968:Dehydroandrosterone
4865:11-Ketotestosterone
4657:cyproterone acetate
4565:prolactin releasers
4507:Cyproterone acetate
4489:Abiraterone acetate
4349:Nomegestrol acetate
4324:Delmadinone acetate
4319:Cyproterone acetate
4301:Abiraterone acetate
3833:Testosterone esters
3665:10.2147/OTT.S147168
3238:2009Sci...324..787T
3008:2015NatSR...512007M
2829:Br J Clin Pharmacol
2601:10.1155/2013/981684
2249:(Suppl 3): S22-31.
1906:. 14 October 2020.
1810:. 27 October 2020.
1633:Apalutamide is the
1624:Society and culture
1452:structural analogue
1351:Peak concentrations
1226:abiraterone acetate
921:are used to treat.
919:abiraterone acetate
865:dihydrotestosterone
829:underactive thyroid
813:high blood pressure
773:among others, is a
267:(Prescription only)
243:(Prescription only)
36:
8037:FG-7142 (ZK-31906)
7583:Nonbenzodiazepines
5791:Dihydroethisterone
5654:Dimethyltrienolone
5614:Methylepitiostanol
5592:Metenolone acetate
5525:Methyltestosterone
5428:19-Norandrosterone
5401:Trestolone acetate
5369:Trenbolone acetate
5313:-nitrosocarbamate)
5202:Stenbolone acetate
5092:Bolazine capronate
4944:Clostebol caproate
4737:Never to phase III
4603:diethylstilbestrol
4230:GnRH (gonadorelin)
4034:Methyltestosterone
3969:Trenbolone acetate
3925:Stenbolone acetate
3890:Bolazine capronate
3793:Clostebol caproate
3504:(suppl_6): vi265.
3498:Annals of Oncology
3463:(suppl_6): vi263.
3457:Annals of Oncology
3179:Clin Pharmacokinet
2996:Scientific Reports
2752:10.1002/iju5.12420
2507:10.1002/cncr.28929
2255:10.3747/co.19.1281
1602:patent application
1175:, and hence is an
1083:There is no known
1024:side effects like
966:medical castration
8978:
8977:
8938:
8937:
8860:2-Hydroxysaclofen
8641:
8640:
8531:Isonipecotic acid
7896:Anabolic steroids
7866:α5IA (LS-193,268)
7776:Dihydrosecurinine
7661:Pyrazolopyridines
7430:potassium bromide
7428:compounds (e.g.,
7391:Anabolic steroids
7369:for a full list):
7223:Isonipecotic acid
7057:
7056:
7017:
7016:
6987:
6980:
6973:
6966:
6898:
6897:
6421:Osaterone acetate
6381:Megestrol acetate
6246:Allyltestosterone
6022:Acetothiolutamide
5941:Megestrol acetate
5744:Vinyltestosterone
5649:Dimethyldienolone
5468:Ethyltestosterone
5396:Trestolone (MENT)
5328:Nandrolone esters
5309:-(2-chloroethyl)-
5185:Nisterime acetate
5062:3α-Androstanediol
5047:1-Androstenedione
4956:Cloxotestosterone
4939:Clostebol acetate
4860:5-Androstenedione
4806:Androgen receptor
4772:
4771:
4706:
4705:
4673:megestrol acetate
4546:Antigonadotropins
4540:
4539:
4497:Aminoglutethimide
4354:Osaterone acetate
4344:Megestrol acetate
4267:
4266:
3940:Nandrolone esters
3788:Clostebol acetate
3587:. 10 April 2024.
3391:(28): 3525–3530.
3102:Journal of Cancer
3016:10.1038/srep12007
2883:978-0-12-417206-7
2841:10.1111/bcp.15336
2654:10.4161/cbt.26724
1874:. 2 August 2023.
1450:Apalutamide is a
1401:active metabolite
1185:pharmacologically
1169:androgen receptor
1165:silent antagonist
1105:drug interactions
1026:breast tenderness
930:Contraindications
925:Contraindications
853:biological target
849:androgen receptor
843:, and acts as an
837:drug interactions
783:androgen receptor
764:
763:
710:Interactive image
588:CompTox Dashboard
287:
275:
262:
250:
238:
158:
125:
27:Chemical compound
16:(Redirected from
9095:
9063:Progonadotropins
8995:
8994:
8993:
8986:
8685:4-Fluorophenibut
8665:
8661:
8652:
8521:Gaboxadol (THIP)
8438:Allopregnanolone
8340:
8336:
8071:Fluoroquinolones
7826:Thiocolchicoside
7646:Piperidinediones
7603:imidazopyridines
7559:allopregnanolone
7466:Dihydroergolines
7381:drinking alcohol
7272:allopregnanolone
7188:Gaboxadol (THIP)
7123:
7119:
7110:
7093:
7084:
7077:
7070:
7061:
7005:
7001:
6985:
6978:
6971:
6964:
6909:
6691:Ketodarolutamide
6671:Hydroxyflutamide
6628:(via metabolite
5997:
5993:
5948:Others/unsorted:
5619:Methylstenbolone
5483:Hydroxystenozole
5042:1-Androstenediol
4840:4-Androstenediol
4827:
4823:
4819:
4799:
4792:
4785:
4776:
4639:GnRH antagonists
4615:ethinylestradiol
4611:estradiol esters
4441:
4288:
4284:
4278:
4259:
4255:
4250:
4246:
4204:Progonadotropins
3869:Testoviron Depot
3760:
3756:
3750:
3745:
3741:
3715:
3708:
3701:
3692:
3687:
3677:
3667:
3652:OncoTargets Ther
3633:
3632:
3630:
3607:
3601:
3600:
3598:
3596:
3577:
3564:
3563:
3561:
3559:
3544:
3538:
3537:
3531:
3523:
3513:
3489:
3483:
3482:
3472:
3448:
3442:
3441:
3425:
3419:
3418:
3408:
3376:
3370:
3362:
3361:
3357:
3350:
3344:
3343:
3341:
3339:
3320:
3311:
3310:
3274:
3268:
3267:
3257:
3232:(5928): 787–90.
3217:
3211:
3210:
3174:
3168:
3167:
3165:
3163:
3157:
3150:
3142:
3136:
3135:
3125:
3114:10.7150/jca.7773
3093:
3087:
3086:
3076:
3044:
3038:
3037:
3027:
2987:
2981:
2980:
2970:
2947:Cancer Discovery
2938:
2932:
2931:
2921:
2906:Cancer Discovery
2897:
2891:
2890:
2867:
2861:
2860:
2823:
2817:
2816:
2780:
2774:
2773:
2763:
2731:
2725:
2724:
2706:
2682:
2676:
2675:
2665:
2633:
2624:
2623:
2613:
2603:
2579:
2568:
2567:
2539:
2528:
2527:
2509:
2485:
2476:
2475:
2465:
2433:
2418:
2410:
2409:
2405:
2398:
2389:
2388:
2378:
2346:
2323:
2322:
2286:
2277:
2276:
2266:
2243:Current Oncology
2234:
2225:
2224:
2214:
2182:
2165:
2164:
2128:
2097:
2096:
2094:
2092:
2072:
2053:
2052:
2050:
2048:
2043:on 23 April 2019
2027:
2012:
2011:
2001:
1969:
1960:
1959:
1957:
1955:
1933:
1920:
1919:
1917:
1915:
1894:
1888:
1887:
1885:
1883:
1862:
1856:
1855:
1853:
1851:
1845:
1838:
1830:
1824:
1823:
1821:
1819:
1800:
1695:
1694:
1692:
1690:
1681:. 20 July 2020.
1671:
1596:, a division of
1573:
1559:
1545:
1531:
1517:
1503:
1479:first-generation
1343:area-under-curve
1322:Pharmacokinetics
1306:
1302:
1232:Other activities
1209:for the AR than
1148:Pharmacodynamics
712:
692:
680:
674:
668:
662:
656:
650:
633:
622:
611:
610:
596:
594:
579:
559:
539:
519:
499:
479:
469:
468:
454:
447:
426:-methylbenzamide
375:
366:
362:
326:
322:Apalutamide: 96%
285:
282:
273:
270:
260:
257:
249:
246:
236:
233:
211:
156:
153:
135:
124:
121:
108:
94:
53:
44:
37:
35:
21:
9103:
9102:
9098:
9097:
9096:
9094:
9093:
9092:
9078:Spiro compounds
9068:Prostate cancer
9023:CYP3A4 inducers
9003:
9002:
9001:
8991:
8989:
8981:
8979:
8974:
8961:
8934:
8663:
8660:
8637:
8365:Homohypotaurine
8338:
8334:
8324:
8197:Phenylsilatrane
7739:chloral hydrate
7706:Sulfonylalkanes
7595:cyclopyrrolones
7416:Benzodiazepines
7168:Dihydromuscimol
7121:
7118:
7099:
7088:
7058:
7053:
7013:
7003:
6894:
6616:Cyanonilutamide
6545:Bavdegalutamide
6356:Epitestosterone
6196:
6027:Acetoxolutamide
5995:
5985:
5694:Norethandrolone
5669:Methyldienolone
5473:Fluoxymesterone
5283:Dimethandrolone
5143:Epiandrosterone
4821:
4811:
4803:
4773:
4768:
4742:
4727:Clinical trials
4702:
4678:
4557:
4536:
4477:
4435:
4434:Steroidogenesis
4428:
4286:
4263:
4257:
4248:
4198:
4114:Norethandrolone
3999:Fluoxymesterone
3758:
3743:
3736:
3728:
3719:
3645:
3642:
3640:Further reading
3637:
3636:
3609:
3608:
3604:
3594:
3592:
3579:
3578:
3567:
3557:
3555:
3546:
3545:
3541:
3524:
3491:
3490:
3486:
3450:
3449:
3445:
3427:
3426:
3422:
3378:
3377:
3373:
3368:Wayback Machine
3359:
3352:
3351:
3347:
3337:
3335:
3322:
3321:
3314:
3285:(10): 1651–61.
3276:
3275:
3271:
3219:
3218:
3214:
3176:
3175:
3171:
3161:
3159:
3155:
3148:
3144:
3143:
3139:
3095:
3094:
3090:
3046:
3045:
3041:
2989:
2988:
2984:
2940:
2939:
2935:
2899:
2898:
2894:
2884:
2869:
2868:
2864:
2825:
2824:
2820:
2785:Respir Investig
2782:
2781:
2777:
2733:
2732:
2728:
2684:
2683:
2679:
2635:
2634:
2627:
2588:Prostate Cancer
2581:
2580:
2571:
2541:
2540:
2531:
2487:
2486:
2479:
2435:
2434:
2421:
2416:Wayback Machine
2407:
2400:
2399:
2392:
2361:(6): 1494–503.
2355:Cancer Research
2348:
2347:
2326:
2288:
2287:
2280:
2236:
2235:
2228:
2184:
2183:
2168:
2130:
2129:
2100:
2090:
2088:
2074:
2073:
2056:
2046:
2044:
2029:
2028:
2015:
1984:(28): 3525–30.
1971:
1970:
1963:
1953:
1951:
1935:
1934:
1923:
1913:
1911:
1896:
1895:
1891:
1881:
1879:
1864:
1863:
1859:
1849:
1847:
1843:
1836:
1832:
1831:
1827:
1817:
1815:
1802:
1801:
1698:
1688:
1686:
1673:
1672:
1668:
1663:
1655:
1647:
1631:
1626:
1586:
1581:
1580:
1577:
1574:
1565:
1560:
1551:
1546:
1537:
1532:
1523:
1518:
1509:
1504:
1494:
1448:
1438:
1383:Apalutamide is
1334:bioavailability
1324:
1311:in comparison.
1304:
1301:
1287:
1242:cytochrome P450
1234:
1155:
1150:
1145:
1101:
1081:
954:clinical trials
946:
927:
887:Apalutamide is
885:
779:prostate cancer
760:
757:
752:
747:
746:
735:
732:
727:
726:
715:
690:
677:
671:
665:
659:
653:
614:
590:
582:
562:
542:
522:
502:
482:
465:
457:
430:
427:
418:
417:
397:
373:
364:
323:
318:Protein binding
308:Bioavailability
300:Pharmacokinetic
294:
215:
171:
164:
145:
138:
68:Erleada, others
28:
23:
22:
15:
12:
11:
5:
9101:
9099:
9091:
9090:
9085:
9080:
9075:
9070:
9065:
9060:
9055:
9050:
9045:
9043:Imidazolidines
9040:
9035:
9030:
9025:
9020:
9015:
9005:
9004:
9000:
8999:
8976:
8975:
8973:
8972:
8965:
8959:
8954:
8947:
8943:
8940:
8939:
8936:
8935:
8933:
8932:
8923:
8922:
8917:
8912:
8907:
8902:
8897:
8892:
8887:
8882:
8877:
8872:
8867:
8862:
8853:
8852:
8847:
8842:
8837:
8832:
8827:
8822:
8817:
8812:
8803:
8802:
8797:
8792:
8787:
8782:
8780:Sodium oxybate
8777:
8772:
8767:
8762:
8757:
8752:
8747:
8742:
8737:
8732:
8727:
8722:
8717:
8712:
8707:
8702:
8697:
8692:
8687:
8682:
8677:
8675:1,4-Butanediol
8668:
8666:
8658:
8649:
8643:
8642:
8639:
8638:
8636:
8635:
8630:
8625:
8620:
8615:
8601:
8596:
8591:
8582:
8581:
8576:
8568:
8563:
8558:
8553:
8548:
8543:
8538:
8533:
8528:
8523:
8518:
8513:
8508:
8503:
8495:
8490:
8485:
8480:
8475:
8470:
8465:
8456:
8455:
8450:
8445:
8440:
8431:
8430:
8425:
8420:
8415:
8410:
8405:
8400:
8392:
8387:
8382:
8377:
8372:
8367:
8362:
8357:
8352:
8343:
8341:
8332:
8326:
8325:
8323:
8322:
8317:
8312:
8307:
8302:
8297:
8292:
8287:
8282:
8277:
8272:
8267:
8262:
8257:
8252:
8247:
8242:
8237:
8232:
8227:
8222:
8217:
8199:
8194:
8189:
8184:
8158:
8153:
8148:
8143:
8138:
8133:
8128:
8123:
8118:
8113:
8108:
8103:
8098:
8093:
8088:
8083:
8078:
8068:
8063:
8049:
8039:
8034:
8029:
8024:
8019:
8014:
8009:
8004:
7999:
7994:
7989:
7984:
7979:
7974:
7969:
7964:
7959:
7954:
7936:
7931:
7926:
7919:cephalosporins
7908:
7903:
7898:
7893:
7888:
7883:
7878:
7873:
7868:
7863:
7858:
7853:
7848:
7843:
7834:
7833:
7828:
7823:
7818:
7813:
7808:
7803:
7798:
7793:
7788:
7783:
7778:
7773:
7768:
7759:
7758:
7728:
7725:valerenic acid
7718:
7713:
7703:
7698:
7688:
7683:
7678:
7671:Quinazolinones
7668:
7658:
7653:
7643:
7638:
7628:
7623:
7618:
7580:
7575:
7570:
7552:
7547:
7542:
7537:
7527:
7517:
7512:
7507:
7493:
7490:mefenamic acid
7483:
7478:
7473:
7463:
7458:
7453:
7448:
7443:
7433:
7423:
7413:
7403:
7393:
7388:
7374:
7361:
7360:
7355:
7350:
7345:
7335:
7330:
7325:
7320:
7315:
7310:
7305:
7300:
7295:
7290:
7285:
7280:
7275:
7265:
7260:
7255:
7250:
7245:
7235:
7230:
7225:
7220:
7215:
7210:
7205:
7200:
7195:
7190:
7185:
7180:
7175:
7170:
7165:
7160:
7155:
7150:
7140:
7135:
7126:
7124:
7116:
7107:
7101:
7100:
7089:
7087:
7086:
7079:
7072:
7064:
7055:
7054:
7052:
7051:
7046:
7041:
7036:
7031:
7026:
7022:
7019:
7018:
7015:
7014:
7012:
7011:
7006:
6996:
6991:
6967:-α-Amino acids
6961:
6956:
6951:
6946:
6915:
6913:
6906:
6900:
6899:
6896:
6895:
6893:
6892:
6887:
6882:
6877:
6872:
6867:
6862:
6857:
6852:
6847:
6842:
6837:
6832:
6827:
6822:
6817:
6812:
6807:
6802:
6797:
6792:
6787:
6782:
6777:
6772:
6767:
6762:
6757:
6752:
6744:
6736:
6728:
6723:
6718:
6713:
6708:
6703:
6698:
6693:
6688:
6683:
6678:
6673:
6668:
6663:
6658:
6653:
6648:
6643:
6638:
6633:
6623:
6618:
6613:
6608:
6603:
6598:
6593:
6588:
6583:
6557:
6552:
6547:
6542:
6537:
6532:
6527:
6522:
6517:
6512:
6507:
6494:
6493:
6488:
6483:
6478:
6473:
6468:
6463:
6461:Spironolactone
6458:
6453:
6448:
6443:
6438:
6433:
6428:
6423:
6418:
6413:
6408:
6403:
6398:
6393:
6388:
6383:
6378:
6373:
6368:
6363:
6358:
6353:
6348:
6343:
6338:
6333:
6328:
6323:
6318:
6313:
6308:
6303:
6298:
6293:
6288:
6286:Cyproheptadine
6283:
6278:
6273:
6268:
6263:
6261:Canrenoic acid
6258:
6253:
6248:
6243:
6238:
6233:
6228:
6223:
6218:
6213:
6204:
6202:
6198:
6197:
6195:
6194:
6189:
6184:
6179:
6170:
6169:
6164:
6159:
6154:
6149:
6144:
6139:
6134:
6129:
6124:
6119:
6114:
6109:
6104:
6099:
6094:
6089:
6084:
6079:
6074:
6069:
6064:
6059:
6054:
6049:
6044:
6039:
6034:
6029:
6024:
6019:
6014:
6009:
6000:
5998:
5987:
5986:
5984:
5983:
5978:
5973:
5968:
5963:
5958:
5953:
5944:
5943:
5938:
5933:
5924:
5923:
5918:
5909:
5908:
5903:
5902:
5901:
5891:
5889:Norgestrienone
5886:
5881:
5867:
5865:Norethisterone
5862:
5861:
5860:
5850:
5840:
5838:Levonorgestrel
5835:
5830:
5825:
5824:
5823:
5813:
5808:
5803:
5794:
5793:
5788:
5783:
5774:
5773:
5768:
5767:
5766:
5756:
5747:
5746:
5737:
5736:
5727:
5726:
5721:
5712:
5711:
5706:
5701:
5696:
5691:
5686:
5681:
5676:
5671:
5666:
5661:
5659:Ethyldienolone
5656:
5651:
5646:
5637:
5636:
5631:
5626:
5621:
5616:
5611:
5606:
5601:
5600:
5599:
5594:
5584:
5579:
5574:
5569:
5564:
5562:Androisoxazole
5555:
5554:
5549:
5544:
5539:
5538:
5537:
5522:
5517:
5516:
5515:
5510:
5505:
5500:
5490:
5485:
5480:
5475:
5470:
5465:
5460:
5455:
5450:
5445:
5440:
5431:
5430:
5425:
5420:
5411:
5410:
5409:
5408:
5403:
5393:
5388:
5387:
5386:
5381:
5376:
5371:
5361:
5360:
5359:
5349:
5344:
5343:
5342:
5332:
5331:
5330:
5320:
5315:
5302:
5301:
5300:
5295:
5290:
5280:
5275:
5270:
5265:
5260:
5259:
5258:
5248:
5243:
5238:
5233:
5232:
5231:
5221:
5212:
5211:
5206:
5205:
5204:
5194:
5189:
5188:
5187:
5177:
5175:Methyldiazinol
5172:
5171:
5170:
5160:
5155:
5150:
5145:
5140:
5139:
5138:
5128:
5127:
5126:
5111:
5106:
5101:
5096:
5095:
5094:
5084:
5079:
5074:
5069:
5064:
5059:
5057:1-Testosterone
5054:
5049:
5044:
5035:
5034:
5033:
5032:
5027:
5012:
5007:
5002:
4997:
4992:
4987:
4986:
4985:
4980:
4970:
4965:
4964:
4963:
4953:
4952:
4951:
4946:
4941:
4931:
4926:
4925:
4924:
4914:
4909:
4904:
4903:
4902:
4897:
4892:
4887:
4877:
4872:
4867:
4862:
4857:
4852:
4847:
4842:
4833:
4831:
4824:
4813:
4812:
4804:
4802:
4801:
4794:
4787:
4779:
4770:
4769:
4767:
4766:
4761:
4756:
4751:
4746:
4741:
4740:
4739:
4738:
4735:
4724:
4718:
4712:
4711:
4708:
4707:
4704:
4703:
4701:
4700:
4695:
4686:
4684:
4680:
4679:
4677:
4676:
4646:
4636:
4626:
4623:paroxypropione
4592:
4585:chlorpromazine
4573:metoclopramide
4555:
4550:
4548:
4542:
4541:
4538:
4537:
4535:
4534:
4532:Spironolactone
4529:
4524:
4519:
4514:
4509:
4504:
4499:
4494:
4485:
4483:
4479:
4478:
4476:
4475:
4470:
4465:
4460:
4455:
4449:
4447:
4438:
4430:
4429:
4427:
4426:
4421:
4416:
4411:
4406:
4401:
4396:
4391:
4386:
4381:
4372:
4371:
4369:Spironolactone
4366:
4361:
4356:
4351:
4346:
4341:
4336:
4331:
4326:
4321:
4316:
4311:
4306:
4294:
4292:
4275:
4269:
4268:
4265:
4264:
4262:
4261:
4237:
4223:
4208:
4206:
4200:
4199:
4197:
4196:
4187:
4186:
4181:
4178:norgestrienone
4162:levonorgestrel
4151:
4146:
4137:
4136:
4127:
4126:
4121:
4116:
4111:
4106:
4097:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4064:Androisoxazole
4057:
4056:
4051:
4046:
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3977:
3976:
3971:
3966:
3961:
3956:
3951:
3937:
3928:
3927:
3922:
3917:
3912:
3907:
3902:
3897:
3892:
3887:
3882:
3873:
3872:
3830:
3825:
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3766:
3764:
3747:
3730:
3729:
3720:
3718:
3717:
3710:
3703:
3695:
3689:
3688:
3641:
3638:
3635:
3634:
3602:
3565:
3539:
3484:
3443:
3420:
3371:
3354:US 20100190991
3345:
3312:
3269:
3212:
3185:(13): 855–78.
3169:
3137:
3088:
3059:(9): 1007–17.
3039:
2982:
2933:
2892:
2882:
2862:
2835:(2): 440–448.
2818:
2791:(5): 700–705.
2775:
2746:(3): 153–155.
2726:
2677:
2625:
2569:
2529:
2477:
2442:Cancer Journal
2419:
2390:
2324:
2297:(6): 553–559.
2278:
2226:
2166:
2139:(6): 699–705.
2098:
2054:
2013:
1961:
1937:"Erleada EPAR"
1921:
1889:
1857:
1825:
1696:
1665:
1664:
1662:
1659:
1654:
1651:
1646:
1643:
1630:
1627:
1625:
1622:
1609:clinical trial
1585:
1582:
1579:
1578:
1575:
1568:
1566:
1561:
1554:
1552:
1547:
1540:
1538:
1533:
1526:
1524:
1519:
1512:
1510:
1505:
1498:
1495:
1492:
1491:
1437:
1434:
1418:auto-induction
1323:
1320:
1299:
1285:
1265:P-glycoprotein
1233:
1230:
1171:(AR), via the
1154:
1151:
1149:
1146:
1144:
1141:
1125:P-glycoprotein
1100:
1097:
1080:
1077:
1065:hepatotoxicity
998:hypothyroidism
994:bone fractures
978:abdominal pain
950:well tolerated
945:
942:
926:
923:
884:
881:
873:prostate gland
825:bone fractures
805:abdominal pain
762:
761:
759:
758:
755:
753:
750:
742:
741:
740:
737:
736:
734:
733:
730:
722:
721:
720:
717:
716:
714:
713:
705:
703:
695:
694:
688:
682:
681:
675:
669:
663:
657:
651:
646:
640:
639:
635:
634:
624:
616:
615:
613:
612:
604:DTXSID40241899
599:
597:
584:
583:
581:
580:
572:
570:
564:
563:
561:
560:
552:
550:
544:
543:
541:
540:
532:
530:
524:
523:
521:
520:
512:
510:
504:
503:
501:
500:
492:
490:
484:
483:
481:
480:
472:
470:
459:
458:
456:
455:
448:
440:
438:
432:
431:
429:
428:
421:
413:
412:
411:
408:
407:
403:
402:
391:
385:
384:
377:
368:
367:
356:
350:
349:
335:
329:
328:
320:
314:
313:
310:
304:
303:
296:
295:
293:
292:
289:
280:
268:
255:
244:
230:
228:
222:
221:
217:
216:
214:
213:
200:
198:
192:
191:
186:
180:
179:
174:
172:administration
166:
165:
163:
162:
160:
150:
148:
140:
139:
137:
136:
118:
116:
110:
109:
102:
96:
95:
88:
78:
77:
74:
70:
69:
66:
60:
59:
55:
54:
46:
45:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
9100:
9089:
9086:
9084:
9081:
9079:
9076:
9074:
9071:
9069:
9066:
9064:
9061:
9059:
9056:
9054:
9051:
9049:
9046:
9044:
9041:
9039:
9036:
9034:
9031:
9029:
9026:
9024:
9021:
9019:
9016:
9014:
9011:
9010:
9008:
8998:
8988:
8984:
8971:
8970:
8966:
8964:
8963:
8955:
8953:
8952:
8948:
8945:
8944:
8941:
8931:
8928:
8925:
8924:
8921:
8918:
8916:
8913:
8911:
8908:
8906:
8903:
8901:
8898:
8896:
8893:
8891:
8888:
8886:
8883:
8881:
8878:
8876:
8873:
8871:
8868:
8866:
8863:
8861:
8858:
8855:
8854:
8851:
8848:
8846:
8843:
8841:
8838:
8836:
8833:
8831:
8828:
8826:
8823:
8821:
8818:
8816:
8813:
8811:
8808:
8805:
8804:
8801:
8798:
8796:
8793:
8791:
8788:
8786:
8783:
8781:
8778:
8776:
8773:
8771:
8768:
8766:
8763:
8761:
8758:
8756:
8753:
8751:
8748:
8746:
8743:
8741:
8738:
8736:
8733:
8731:
8728:
8726:
8723:
8721:
8718:
8716:
8713:
8711:
8708:
8706:
8703:
8701:
8698:
8696:
8693:
8691:
8690:Aceburic acid
8688:
8686:
8683:
8681:
8678:
8676:
8673:
8670:
8669:
8667:
8662:
8653:
8650:
8648:
8644:
8634:
8631:
8629:
8626:
8624:
8621:
8619:
8616:
8613:
8609:
8605:
8602:
8600:
8597:
8595:
8592:
8590:
8587:
8584:
8583:
8580:
8577:
8575:
8573:
8569:
8567:
8564:
8562:
8559:
8557:
8554:
8552:
8549:
8547:
8544:
8542:
8539:
8537:
8534:
8532:
8529:
8527:
8524:
8522:
8519:
8517:
8514:
8512:
8509:
8507:
8504:
8502:
8500:
8496:
8494:
8491:
8489:
8486:
8484:
8481:
8479:
8476:
8474:
8471:
8469:
8466:
8464:
8461:
8458:
8457:
8454:
8451:
8449:
8446:
8444:
8441:
8439:
8436:
8433:
8432:
8429:
8426:
8424:
8421:
8419:
8416:
8414:
8411:
8409:
8406:
8404:
8401:
8399:
8397:
8393:
8391:
8388:
8386:
8383:
8381:
8380:Ibotenic acid
8378:
8376:
8373:
8371:
8368:
8366:
8363:
8361:
8358:
8356:
8353:
8351:
8348:
8345:
8344:
8342:
8337:
8327:
8321:
8318:
8316:
8313:
8311:
8308:
8306:
8303:
8301:
8298:
8296:
8293:
8291:
8288:
8286:
8283:
8281:
8278:
8276:
8273:
8271:
8268:
8266:
8263:
8261:
8258:
8256:
8253:
8251:
8248:
8246:
8243:
8241:
8238:
8236:
8233:
8231:
8228:
8226:
8225:Propybicyphat
8223:
8221:
8218:
8215:
8211:
8207:
8203:
8200:
8198:
8195:
8193:
8190:
8188:
8187:Oenanthotoxin
8185:
8182:
8178:
8174:
8170:
8166:
8162:
8159:
8157:
8154:
8152:
8149:
8147:
8144:
8142:
8139:
8137:
8134:
8132:
8129:
8127:
8124:
8122:
8119:
8117:
8114:
8112:
8109:
8107:
8104:
8102:
8099:
8097:
8096:Iomazenil (I)
8094:
8092:
8089:
8087:
8084:
8082:
8079:
8076:
8075:ciprofloxacin
8072:
8069:
8067:
8064:
8061:
8057:
8056:amentoflavone
8053:
8050:
8047:
8043:
8040:
8038:
8035:
8033:
8030:
8028:
8025:
8023:
8020:
8018:
8015:
8013:
8010:
8008:
8005:
8003:
8000:
7998:
7995:
7993:
7992:Cyclothiazide
7990:
7988:
7985:
7983:
7980:
7978:
7975:
7973:
7970:
7968:
7965:
7963:
7960:
7958:
7955:
7952:
7948:
7944:
7940:
7937:
7935:
7932:
7930:
7927:
7924:
7920:
7916:
7912:
7909:
7907:
7904:
7902:
7899:
7897:
7894:
7892:
7889:
7887:
7884:
7882:
7879:
7877:
7874:
7872:
7869:
7867:
7864:
7862:
7859:
7857:
7854:
7852:
7849:
7847:
7844:
7842:
7839:
7836:
7835:
7832:
7829:
7827:
7824:
7822:
7819:
7817:
7814:
7812:
7809:
7807:
7804:
7802:
7799:
7797:
7794:
7792:
7789:
7787:
7784:
7782:
7781:Famiraprinium
7779:
7777:
7774:
7772:
7769:
7767:
7764:
7761:
7760:
7756:
7752:
7748:
7747:diethyl ether
7744:
7740:
7736:
7732:
7729:
7726:
7722:
7719:
7717:
7714:
7711:
7707:
7704:
7702:
7699:
7696:
7692:
7689:
7687:
7684:
7682:
7679:
7676:
7672:
7669:
7666:
7662:
7659:
7657:
7654:
7651:
7647:
7644:
7642:
7639:
7636:
7632:
7629:
7627:
7624:
7622:
7621:Norfluoxetine
7619:
7616:
7612:
7608:
7604:
7600:
7596:
7592:
7588:
7584:
7581:
7579:
7576:
7574:
7571:
7568:
7564:
7560:
7556:
7553:
7551:
7548:
7546:
7543:
7541:
7538:
7535:
7531:
7528:
7525:
7521:
7518:
7516:
7513:
7511:
7508:
7505:
7501:
7497:
7494:
7491:
7487:
7484:
7482:
7479:
7477:
7474:
7471:
7467:
7464:
7462:
7461:Clomethiazole
7459:
7457:
7456:Chlormezanone
7454:
7452:
7449:
7447:
7446:Carbamazepine
7444:
7441:
7437:
7434:
7431:
7427:
7424:
7421:
7417:
7414:
7411:
7410:phenobarbital
7407:
7404:
7401:
7397:
7394:
7392:
7389:
7386:
7382:
7378:
7375:
7373:
7370:
7368:
7363:
7362:
7359:
7356:
7354:
7351:
7349:
7346:
7343:
7339:
7336:
7334:
7331:
7329:
7326:
7324:
7321:
7319:
7316:
7314:
7313:Quisqualamine
7311:
7309:
7306:
7304:
7301:
7299:
7296:
7294:
7291:
7289:
7286:
7284:
7281:
7279:
7276:
7273:
7269:
7266:
7264:
7261:
7259:
7256:
7254:
7251:
7249:
7248:Methylglyoxal
7246:
7243:
7239:
7236:
7234:
7231:
7229:
7226:
7224:
7221:
7219:
7216:
7214:
7211:
7209:
7206:
7204:
7201:
7199:
7198:Ibotenic acid
7196:
7194:
7191:
7189:
7186:
7184:
7181:
7179:
7176:
7174:
7171:
7169:
7166:
7164:
7161:
7159:
7156:
7154:
7151:
7148:
7147:phenobarbital
7144:
7141:
7139:
7136:
7134:
7131:
7128:
7127:
7125:
7120:
7111:
7108:
7106:
7102:
7098:
7095:
7085:
7080:
7078:
7073:
7071:
7066:
7065:
7062:
7050:
7047:
7045:
7042:
7040:
7037:
7035:
7032:
7030:
7027:
7024:
7023:
7020:
7010:
7007:
7002:
6997:
6995:
6992:
6989:
6982:
6975:
6968:
6962:
6960:
6957:
6955:
6952:
6950:
6947:
6944:
6940:
6936:
6932:
6928:
6924:
6920:
6917:
6916:
6914:
6910:
6907:
6905:
6901:
6891:
6888:
6886:
6883:
6881:
6878:
6876:
6873:
6871:
6870:Valproic acid
6868:
6866:
6863:
6861:
6858:
6856:
6853:
6851:
6848:
6846:
6843:
6841:
6838:
6836:
6833:
6831:
6828:
6826:
6823:
6821:
6818:
6816:
6815:Rezvilutamide
6813:
6811:
6808:
6806:
6803:
6801:
6798:
6796:
6793:
6791:
6790:Proxalutamide
6788:
6786:
6783:
6781:
6778:
6776:
6773:
6771:
6768:
6766:
6763:
6761:
6758:
6756:
6753:
6751:
6749:
6745:
6743:
6741:
6737:
6735:
6733:
6729:
6727:
6724:
6722:
6719:
6717:
6714:
6712:
6709:
6707:
6704:
6702:
6699:
6697:
6694:
6692:
6689:
6687:
6684:
6682:
6679:
6677:
6674:
6672:
6669:
6667:
6664:
6662:
6659:
6657:
6654:
6652:
6649:
6647:
6644:
6642:
6639:
6637:
6634:
6631:
6627:
6624:
6622:
6619:
6617:
6614:
6612:
6609:
6607:
6604:
6602:
6599:
6597:
6594:
6592:
6589:
6587:
6584:
6581:
6577:
6573:
6569:
6565:
6561:
6558:
6556:
6553:
6551:
6548:
6546:
6543:
6541:
6538:
6536:
6533:
6531:
6528:
6526:
6523:
6521:
6518:
6516:
6513:
6511:
6508:
6506:
6505:-Bicalutamide
6504:
6499:
6498:Nonsteroidal:
6496:
6495:
6492:
6489:
6487:
6484:
6482:
6479:
6477:
6474:
6472:
6469:
6467:
6464:
6462:
6459:
6457:
6454:
6452:
6449:
6447:
6444:
6442:
6439:
6437:
6434:
6432:
6429:
6427:
6424:
6422:
6419:
6417:
6414:
6412:
6409:
6407:
6404:
6402:
6399:
6397:
6394:
6392:
6389:
6387:
6384:
6382:
6379:
6377:
6374:
6372:
6369:
6367:
6366:Guggulsterone
6364:
6362:
6359:
6357:
6354:
6352:
6349:
6347:
6344:
6342:
6339:
6337:
6334:
6332:
6329:
6327:
6324:
6322:
6319:
6317:
6314:
6312:
6309:
6307:
6304:
6302:
6299:
6297:
6294:
6292:
6289:
6287:
6284:
6282:
6279:
6277:
6274:
6272:
6269:
6267:
6264:
6262:
6259:
6257:
6254:
6252:
6249:
6247:
6244:
6242:
6239:
6237:
6234:
6232:
6229:
6227:
6224:
6222:
6219:
6217:
6214:
6212:
6209:
6206:
6205:
6203:
6199:
6193:
6190:
6188:
6185:
6183:
6180:
6178:
6175:
6172:
6171:
6168:
6165:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
6140:
6138:
6135:
6133:
6130:
6128:
6125:
6123:
6120:
6118:
6115:
6113:
6110:
6108:
6105:
6103:
6100:
6098:
6095:
6093:
6090:
6088:
6085:
6083:
6080:
6078:
6075:
6073:
6070:
6068:
6065:
6063:
6060:
6058:
6055:
6053:
6050:
6048:
6045:
6043:
6040:
6038:
6035:
6033:
6030:
6028:
6025:
6023:
6020:
6018:
6015:
6013:
6010:
6008:
6005:
6004:Nonsteroidal:
6002:
6001:
5999:
5994:
5988:
5982:
5979:
5977:
5974:
5972:
5969:
5967:
5964:
5962:
5959:
5957:
5956:5α-Androstane
5954:
5952:
5949:
5946:
5945:
5942:
5939:
5937:
5934:
5932:
5929:
5926:
5925:
5922:
5919:
5917:
5914:
5911:
5910:
5907:
5904:
5900:
5897:
5896:
5895:
5892:
5890:
5887:
5885:
5882:
5879:
5875:
5871:
5868:
5866:
5863:
5859:
5856:
5855:
5854:
5851:
5848:
5844:
5841:
5839:
5836:
5834:
5831:
5829:
5826:
5822:
5819:
5818:
5817:
5814:
5812:
5809:
5807:
5804:
5802:
5799:
5796:
5795:
5792:
5789:
5787:
5784:
5782:
5779:
5776:
5775:
5772:
5769:
5765:
5764:Ethandrostate
5762:
5761:
5760:
5757:
5755:
5752:
5749:
5748:
5745:
5742:
5739:
5738:
5735:
5732:
5729:
5728:
5725:
5722:
5720:
5717:
5714:
5713:
5710:
5707:
5705:
5702:
5700:
5697:
5695:
5692:
5690:
5687:
5685:
5682:
5680:
5677:
5675:
5672:
5670:
5667:
5665:
5664:Ethylestrenol
5662:
5660:
5657:
5655:
5652:
5650:
5647:
5645:
5642:
5639:
5638:
5635:
5632:
5630:
5627:
5625:
5622:
5620:
5617:
5615:
5612:
5610:
5607:
5605:
5602:
5598:
5595:
5593:
5590:
5589:
5588:
5585:
5583:
5580:
5578:
5575:
5573:
5570:
5568:
5565:
5563:
5560:
5557:
5556:
5553:
5550:
5548:
5545:
5543:
5540:
5536:
5533:
5532:
5530:
5526:
5523:
5521:
5518:
5514:
5511:
5509:
5506:
5504:
5501:
5499:
5496:
5495:
5494:
5491:
5489:
5486:
5484:
5481:
5479:
5476:
5474:
5471:
5469:
5466:
5464:
5461:
5459:
5456:
5454:
5451:
5449:
5446:
5444:
5441:
5439:
5436:
5433:
5432:
5429:
5426:
5424:
5421:
5419:
5416:
5413:
5412:
5407:
5404:
5402:
5399:
5398:
5397:
5394:
5392:
5389:
5385:
5382:
5380:
5377:
5375:
5372:
5370:
5367:
5366:
5365:
5362:
5358:
5355:
5354:
5353:
5350:
5348:
5345:
5341:
5338:
5337:
5336:
5333:
5329:
5326:
5325:
5324:
5321:
5319:
5316:
5314:
5312:
5308:
5303:
5299:
5296:
5294:
5291:
5289:
5286:
5285:
5284:
5281:
5279:
5276:
5274:
5271:
5269:
5266:
5264:
5261:
5257:
5254:
5253:
5252:
5249:
5247:
5244:
5242:
5239:
5237:
5234:
5230:
5227:
5226:
5225:
5222:
5220:
5217:
5214:
5213:
5210:
5207:
5203:
5200:
5199:
5198:
5195:
5193:
5190:
5186:
5183:
5182:
5181:
5178:
5176:
5173:
5169:
5166:
5165:
5164:
5161:
5159:
5156:
5154:
5151:
5149:
5146:
5144:
5141:
5137:
5134:
5133:
5132:
5129:
5125:
5122:
5121:
5119:
5115:
5112:
5110:
5107:
5105:
5102:
5100:
5097:
5093:
5090:
5089:
5088:
5085:
5083:
5080:
5078:
5075:
5073:
5070:
5068:
5065:
5063:
5060:
5058:
5055:
5053:
5050:
5048:
5045:
5043:
5040:
5037:
5036:
5031:
5028:
5026:
5023:
5022:
5020:
5016:
5013:
5011:
5008:
5006:
5003:
5001:
4998:
4996:
4993:
4991:
4988:
4984:
4981:
4979:
4976:
4975:
4974:
4971:
4969:
4966:
4962:
4959:
4958:
4957:
4954:
4950:
4947:
4945:
4942:
4940:
4937:
4936:
4935:
4932:
4930:
4927:
4923:
4920:
4919:
4918:
4915:
4913:
4910:
4908:
4905:
4901:
4898:
4896:
4893:
4891:
4888:
4886:
4883:
4882:
4881:
4878:
4876:
4873:
4871:
4868:
4866:
4863:
4861:
4858:
4856:
4853:
4851:
4848:
4846:
4843:
4841:
4838:
4835:
4834:
4832:
4828:
4825:
4820:
4814:
4810:
4807:
4800:
4795:
4793:
4788:
4786:
4781:
4780:
4777:
4765:
4762:
4760:
4757:
4755:
4752:
4750:
4747:
4744:
4743:
4736:
4734:
4731:
4730:
4728:
4725:
4722:
4719:
4717:
4714:
4713:
4709:
4699:
4696:
4694:
4691:
4688:
4687:
4685:
4681:
4674:
4670:
4666:
4662:
4658:
4654:
4650:
4647:
4644:
4640:
4637:
4634:
4630:
4629:GnRH agonists
4627:
4624:
4620:
4616:
4612:
4608:
4604:
4600:
4596:
4593:
4590:
4586:
4582:
4578:
4574:
4570:
4566:
4562:
4559:
4552:
4551:
4549:
4547:
4543:
4533:
4530:
4528:
4525:
4523:
4520:
4518:
4515:
4513:
4510:
4508:
4505:
4503:
4500:
4498:
4495:
4493:
4490:
4487:
4486:
4484:
4480:
4474:
4471:
4469:
4466:
4464:
4461:
4459:
4456:
4454:
4451:
4450:
4448:
4446:
4442:
4439:
4437:
4431:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4400:
4397:
4395:
4392:
4390:
4387:
4385:
4382:
4380:
4377:
4376:Nonsteroidal:
4374:
4373:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4325:
4322:
4320:
4317:
4315:
4312:
4310:
4307:
4305:
4302:
4299:
4296:
4295:
4293:
4291:
4285:
4279:
4276:
4274:
4273:Antiandrogens
4270:
4256:
4247:
4241:
4240:Gonadotropins
4238:
4235:
4231:
4227:
4226:GnRH agonists
4224:
4221:
4217:
4213:
4212:Antiestrogens
4210:
4209:
4207:
4205:
4201:
4195:
4192:
4189:
4188:
4185:
4182:
4179:
4175:
4171:
4167:
4163:
4159:
4155:
4152:
4150:
4147:
4145:
4142:
4139:
4138:
4135:
4132:
4129:
4128:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4104:Ethylestrenol
4102:
4099:
4098:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4059:
4058:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3979:
3978:
3975:
3972:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3949:
3945:
3941:
3938:
3936:
3933:
3930:
3929:
3926:
3923:
3921:
3918:
3916:
3913:
3911:
3908:
3906:
3903:
3901:
3898:
3896:
3893:
3891:
3888:
3886:
3883:
3881:
3878:
3875:
3874:
3870:
3866:
3862:
3858:
3854:
3850:
3846:
3842:
3838:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3768:
3767:
3765:
3763:
3757:
3751:
3748:
3742:
3735:
3731:
3727:
3726:antiandrogens
3723:
3716:
3711:
3709:
3704:
3702:
3697:
3696:
3693:
3685:
3681:
3676:
3671:
3666:
3661:
3658:: 2141–2147.
3657:
3653:
3649:
3644:
3643:
3639:
3629:
3624:
3620:
3616:
3612:
3606:
3603:
3590:
3586:
3582:
3576:
3574:
3572:
3570:
3566:
3553:
3549:
3543:
3540:
3535:
3529:
3521:
3517:
3512:
3507:
3503:
3499:
3495:
3488:
3485:
3480:
3476:
3471:
3466:
3462:
3458:
3454:
3447:
3444:
3439:
3435:
3431:
3424:
3421:
3416:
3412:
3407:
3402:
3398:
3394:
3390:
3386:
3382:
3375:
3372:
3369:
3365:
3355:
3349:
3346:
3333:
3329:
3325:
3319:
3317:
3313:
3308:
3304:
3300:
3296:
3292:
3288:
3284:
3280:
3273:
3270:
3265:
3261:
3256:
3251:
3247:
3243:
3239:
3235:
3231:
3227:
3223:
3216:
3213:
3208:
3204:
3200:
3196:
3192:
3188:
3184:
3180:
3173:
3170:
3154:
3147:
3141:
3138:
3133:
3129:
3124:
3119:
3115:
3111:
3108:(2): 133–42.
3107:
3103:
3099:
3092:
3089:
3084:
3080:
3075:
3070:
3066:
3062:
3058:
3054:
3050:
3043:
3040:
3035:
3031:
3026:
3021:
3017:
3013:
3009:
3005:
3001:
2997:
2993:
2986:
2983:
2978:
2974:
2969:
2964:
2960:
2956:
2952:
2948:
2944:
2937:
2934:
2929:
2925:
2920:
2915:
2912:(9): 1020–9.
2911:
2907:
2903:
2896:
2893:
2889:
2885:
2879:
2875:
2874:
2866:
2863:
2858:
2854:
2850:
2846:
2842:
2838:
2834:
2830:
2822:
2819:
2814:
2810:
2806:
2802:
2798:
2794:
2790:
2786:
2779:
2776:
2771:
2767:
2762:
2757:
2753:
2749:
2745:
2741:
2737:
2730:
2727:
2722:
2718:
2714:
2710:
2705:
2700:
2697:(5): 455–61.
2696:
2692:
2688:
2681:
2678:
2673:
2669:
2664:
2659:
2655:
2651:
2648:(2): 149–55.
2647:
2643:
2639:
2632:
2630:
2626:
2621:
2617:
2612:
2607:
2602:
2597:
2593:
2589:
2585:
2578:
2576:
2574:
2570:
2565:
2561:
2557:
2553:
2549:
2545:
2538:
2536:
2534:
2530:
2525:
2521:
2517:
2513:
2508:
2503:
2500:(3): 361–71.
2499:
2495:
2491:
2484:
2482:
2478:
2473:
2469:
2464:
2459:
2455:
2451:
2447:
2443:
2439:
2432:
2430:
2428:
2426:
2424:
2420:
2417:
2413:
2403:
2402:WO 2007126765
2397:
2395:
2391:
2386:
2382:
2377:
2372:
2368:
2364:
2360:
2356:
2352:
2345:
2343:
2341:
2339:
2337:
2335:
2333:
2331:
2329:
2325:
2320:
2316:
2312:
2308:
2304:
2300:
2296:
2292:
2285:
2283:
2279:
2274:
2270:
2265:
2260:
2256:
2252:
2248:
2244:
2240:
2233:
2231:
2227:
2222:
2218:
2213:
2208:
2204:
2200:
2197:(4): 167–78.
2196:
2192:
2188:
2181:
2179:
2177:
2175:
2173:
2171:
2167:
2162:
2158:
2154:
2150:
2146:
2142:
2138:
2134:
2127:
2125:
2123:
2121:
2119:
2117:
2115:
2113:
2111:
2109:
2107:
2105:
2103:
2099:
2086:
2082:
2078:
2071:
2069:
2067:
2065:
2063:
2061:
2059:
2055:
2042:
2038:
2037:
2032:
2026:
2024:
2022:
2020:
2018:
2014:
2009:
2005:
2000:
1995:
1991:
1987:
1983:
1979:
1975:
1968:
1966:
1962:
1949:
1945:
1943:
1938:
1932:
1930:
1928:
1926:
1922:
1909:
1905:
1904:
1903:Health Canada
1899:
1893:
1890:
1877:
1873:
1872:
1871:Health Canada
1867:
1861:
1858:
1842:
1835:
1829:
1826:
1813:
1809:
1805:
1799:
1797:
1795:
1793:
1791:
1789:
1787:
1785:
1783:
1781:
1779:
1777:
1775:
1773:
1771:
1769:
1767:
1765:
1763:
1761:
1759:
1757:
1755:
1753:
1751:
1749:
1747:
1745:
1743:
1741:
1739:
1737:
1735:
1733:
1731:
1729:
1727:
1725:
1723:
1721:
1719:
1717:
1715:
1713:
1711:
1709:
1707:
1705:
1703:
1701:
1697:
1684:
1680:
1676:
1670:
1667:
1660:
1658:
1652:
1650:
1644:
1642:
1640:
1636:
1629:Generic names
1628:
1623:
1621:
1618:
1614:
1610:
1607:
1603:
1599:
1595:
1591:
1583:
1572:
1567:
1564:
1558:
1553:
1550:
1544:
1539:
1536:
1530:
1525:
1522:
1516:
1511:
1508:
1502:
1497:
1490:
1488:
1484:
1480:
1476:
1473:
1469:
1465:
1461:
1457:
1453:
1447:
1443:
1435:
1433:
1431:
1427:
1423:
1419:
1415:
1410:
1406:
1402:
1398:
1394:
1390:
1386:
1381:
1379:
1376:
1372:
1368:
1364:
1360:
1356:
1352:
1348:
1344:
1339:
1335:
1332:
1329:
1321:
1319:
1317:
1312:
1310:
1303:
1294:
1293:
1289:
1281:
1276:
1274:
1270:
1266:
1262:
1258:
1254:
1250:
1246:
1243:
1240:potential of
1239:
1231:
1229:
1227:
1223:
1218:
1216:
1212:
1208:
1204:
1200:
1197:
1193:
1190:
1186:
1182:
1178:
1174:
1170:
1166:
1163:
1160:
1152:
1147:
1142:
1140:
1138:
1134:
1130:
1126:
1122:
1118:
1114:
1110:
1106:
1098:
1096:
1094:
1090:
1086:
1078:
1076:
1074:
1070:
1066:
1062:
1058:
1054:
1050:
1046:
1043:
1039:
1035:
1031:
1027:
1023:
1019:
1015:
1011:
1010:birth defects
1007:
1003:
1000:, as well as
999:
995:
991:
987:
983:
979:
975:
971:
967:
963:
959:
955:
951:
943:
941:
939:
935:
931:
924:
922:
920:
917:
913:
909:
905:
901:
897:
892:
890:
882:
880:
876:
874:
870:
866:
862:
858:
854:
850:
846:
842:
838:
834:
830:
826:
822:
818:
814:
810:
806:
802:
798:
794:
790:
788:
784:
780:
776:
772:
768:
754:
749:
745:
738:
729:
725:
718:
711:
707:
706:
704:
701:
696:
689:
687:
683:
647:
645:
641:
636:
632:
628:
625:
623:
621:ECHA InfoCard
617:
609:
605:
601:
600:
598:
589:
585:
578:
577:ChEMBL3183409
574:
573:
571:
569:
565:
558:
554:
553:
551:
549:
545:
538:
534:
533:
531:
529:
525:
518:
514:
513:
511:
509:
505:
498:
494:
493:
491:
489:
485:
478:
474:
473:
471:
464:
460:
453:
449:
446:
442:
441:
439:
437:
433:
425:
420:
416:
409:
404:
400:
395:
392:
390:
386:
382:
378:
376:
369:
363:
357:
355:
351:
347:
343:
339:
336:
334:
330:
321:
319:
315:
311:
309:
305:
301:
297:
290:
288: Rx-only
281:
279:
269:
266:
256:
254:
245:
242:
232:
231:
229:
227:
223:
218:
210:
205:
202:
201:
199:
197:
193:
190:
187:
185:
181:
178:
175:
173:
167:
161:
152:
151:
149:
147:
141:
134:
129:
120:
119:
117:
115:
111:
107:
103:
101:
97:
93:
89:
87:
83:
79:
75:
71:
67:
65:
61:
58:Clinical data
56:
52:
47:
43:
38:
30:
19:
9028:Fluoroarenes
9018:Cyclobutanes
8967:
8956:
8949:
8926:
8857:Antagonists:
8856:
8806:
8671:
8647:Metabotropic
8618:Pregnanolone
8612:picrotoxinin
8585:
8571:
8498:
8468:(S)-4-ACPBPA
8463:(S)-2-MeGABA
8460:Antagonists:
8459:
8434:
8423:Thiomuscimol
8395:
8346:
8210:picrotoxinin
8173:enzalutamide
8169:bicalutamide
8164:
8091:Golexanolone
7987:Cloflubicyne
7837:
7763:Antagonists:
7762:
7675:methaqualone
7650:glutethimide
7626:Petrichloral
7587:β-carbolines
7406:Barbiturates
7364:
7348:Thiomuscimol
7153:Beta-Alanine
7143:Barbiturates
7133:(+)-Catechin
7129:
7009:Testosterone
6795:Pyrilutamide
6747:
6739:
6731:
6696:Lavender oil
6686:Ketoconazole
6651:Enzalutamide
6621:Darolutamide
6555:Bicalutamide
6530:Atraric acid
6524:
6502:
6497:
6481:Trimegestone
6436:Promegestone
6401:Mifepristone
6376:Medrogestone
6321:Drospirenone
6276:Clascoterone
6207:
6173:
6117:JNJ-37654032
6112:JNJ-28330835
6107:JNJ-26146900
6003:
5947:
5927:
5912:
5894:Quingestanol
5811:Etonogestrel
5797:
5777:
5750:
5740:
5730:
5715:
5699:Propetandrol
5640:
5629:Oxymetholone
5604:Methasterone
5558:
5552:Tiomesterone
5542:Oxymesterone
5434:
5414:
5335:Norclostebol
5310:
5306:
5215:
5153:Mepitiostane
5148:Epitiostanol
5131:Drostanolone
5082:Androsterone
5038:
5019:+dutasteride
5015:Testosterone
4983:DHEA sulfate
4836:
4689:
4649:Progestogens
4517:Ketoconazole
4445:5α-Reductase
4409:Ketoconazole
4399:Enzalutamide
4394:Darolutamide
4384:Bicalutamide
4378:
4375:
4339:Medrogestone
4334:Drospirenone
4297:
4190:
4140:
4130:
4100:
4089:Oxymetholone
4060:
4044:Oxymesterone
3980:
3954:Norclostebol
3931:
3905:Mepitiostane
3900:Epitiostanol
3876:
3828:Testosterone
3769:
3655:
3651:
3628:10665/331046
3618:
3614:
3605:
3593:. Retrieved
3584:
3556:. Retrieved
3542:
3528:cite journal
3501:
3497:
3487:
3460:
3456:
3446:
3429:
3423:
3388:
3384:
3374:
3348:
3336:. Retrieved
3327:
3282:
3278:
3272:
3229:
3225:
3215:
3182:
3178:
3172:
3160:. Retrieved
3140:
3105:
3101:
3091:
3056:
3052:
3042:
2999:
2995:
2985:
2953:(9): 971–4.
2950:
2946:
2936:
2909:
2905:
2895:
2887:
2872:
2865:
2832:
2828:
2821:
2788:
2784:
2778:
2743:
2740:IJU Case Rep
2739:
2729:
2694:
2690:
2680:
2645:
2641:
2591:
2587:
2550:(1): 11–19.
2547:
2543:
2497:
2493:
2445:
2441:
2358:
2354:
2294:
2290:
2246:
2242:
2194:
2190:
2136:
2132:
2089:. Retrieved
2080:
2045:. Retrieved
2041:the original
2034:
1981:
1977:
1952:. Retrieved
1940:
1912:. Retrieved
1901:
1892:
1880:. Retrieved
1869:
1860:
1848:. Retrieved
1828:
1816:. Retrieved
1807:
1689:28 September
1687:. Retrieved
1678:
1669:
1656:
1653:Availability
1648:
1635:generic name
1632:
1587:
1549:Enzalutamide
1456:enzalutamide
1449:
1382:
1363:bicalutamide
1358:
1355:enzalutamide
1347:Steady-state
1325:
1313:
1290:
1277:
1235:
1222:darolutamide
1219:
1211:bicalutamide
1199:distribution
1192:enzalutamide
1181:structurally
1177:antiandrogen
1156:
1143:Pharmacology
1102:
1099:Interactions
1082:
1069:Case reports
1057:bicalutamide
1045:enzalutamide
1034:feminization
1030:gynecomastia
958:side effects
947:
944:Side effects
928:
912:enzalutamide
893:
886:
883:Medical uses
877:
861:testosterone
841:antiandrogen
793:Side effects
791:
770:
766:
765:
452:1361232-32-7
423:
381:steady-state
372:Elimination
226:Legal status
220:Legal status
114:License data
29:
8930:Compound 14
8760:Lesogaberan
8599:Loreclezole
8536:Loreclezole
8473:(S)-4-ACPCA
8453:Lanthanides
8443:Alphaxolone
8385:Isoguvacine
8295:Terbequinil
8165:apalutamide
8156:Nicardipine
8116:Laudanosine
7923:carbapenems
7915:penicillins
7771:Coriamyrtin
7766:Bicuculline
7755:sevoflurane
7751:paraldehyde
7701:Stiripentol
7578:Niacinamide
7563:cholesterol
7545:Loreclezole
7440:meprobamate
7396:Avermectins
7263:Nefiracetam
7228:Kojic amine
7218:Isomuscimol
7213:Isoguvacine
6994:Osteocalcin
6875:Vinclozolin
6860:Thalidomide
6855:Seviteronel
6785:Procymidone
6721:Masofaniten
6676:Inocoterone
6580:bisphenol S
6576:bisphenol F
6572:bisphenol A
6550:BAY-1024767
6525:Apalutamide
6471:Spiroxasone
6466:Spirorenone
6446:Rosterolone
6386:Mespirenone
6331:Edogestrone
6301:Delanterone
6291:Cyproterone
6281:Clometerone
6251:Benorterone
6236:Abiraterone
6201:Antagonists
6132:PF-06260414
6037:BMS-564,929
5961:Alternariol
5853:Lynestrenol
5806:Desogestrel
5689:Norboletone
5679:Metribolone
5624:Oxandrolone
5582:Mestanolone
5547:Penmesterol
5478:Formebolone
5443:Calusterone
5438:Bolasterone
5192:Prostanozol
5163:Mesterolone
4723:from market
4633:leuprorelin
4581:haloperidol
4577:risperidone
4569:domperidone
4561:antagonists
4527:Seviteronel
4468:Finasteride
4463:Epristeride
4458:Dutasteride
4453:Alfatradiol
4419:Seviteronel
4379:Apalutamide
4290:antagonists
4234:leuprorelin
4174:lynestrenol
4084:Oxandrolone
4079:Mestanolone
4049:Penmesterol
4004:Formebolone
3989:Calusterone
3984:Bolasterone
3910:Mesterolone
3857:Deposterona
3558:15 February
3338:6 September
3328:AdisInsight
3279:ChemMedChem
3162:24 February
2448:(1): 43–9.
2047:15 February
1645:Brand names
1576:Apalutamide
1466:variant of
1385:metabolized
1365:. The mean
1338:peak levels
1316:QT interval
1162:competitive
1111:of CYP3A4,
1047:but unlike
781:. It is an
767:Apalutamide
693: g·mol
627:100.235.115
445:956104-40-8
406:Identifiers
354:Metabolites
100:MedlinePlus
73:Other names
64:Trade names
34:Apalutamide
9013:Benzamides
9007:Categories
8785:SKF-97,541
8695:Arbaclofen
8604:Picrotoxin
8594:Bilobalide
8270:Suritozole
8260:Sarmazenil
8245:Ro 19-4603
8240:Ro 15-4513
8235:Radequinil
8202:Picrotoxin
8181:nilutamide
8151:Naltrexone
8086:Furosemide
8066:Flumazenil
8060:oroxylin A
8052:Flavonoids
8032:Etbicyphat
7962:Bilobalide
7929:Basmisanil
7816:Sinomenine
7811:Securinine
7806:Pitrazepin
7791:Hydrastine
7743:chloroform
7716:Topiramate
7656:Propanidid
7520:Imidazoles
7515:Flupirtine
7510:Fluoxetine
7504:hispidulin
7496:Flavonoids
7451:Chloralose
7436:Carbamates
7400:ivermectin
7338:Terpenoids
7283:PF-6372865
7138:Bamaluzole
7105:Ionotropic
7097:modulators
6988:-ornithine
6931:gadolinium
6780:Prochloraz
6775:Phenothrin
6755:Nilutamide
6726:Methiocarb
6646:Endosulfan
6611:Cioteronel
6606:Cimetidine
6596:BMS-641988
6591:BMS-570511
6586:BMS-501949
6560:Bisphenols
6515:Antarlides
6491:Zanoterone
6426:Oxendolone
6371:Ludaterone
6361:Galeterone
6311:Dicirenone
6208:Steroidal:
6174:Steroidal:
6167:Vosilasarm
6062:GSK2881078
6017:AC-262,536
5976:Trilostane
5884:Norgestrel
5833:Gestrinone
5801:Δ-Tibolone
5684:Mibolerone
5634:Stanozolol
5587:Metenolone
5364:Trenbolone
5323:Nandrolone
5273:Dienedione
5197:Stenbolone
5158:Mesabolone
5010:Silandrone
5005:Quinbolone
5000:Plomestane
4995:Formestane
4990:Exemestane
4912:Atamestane
4809:modulators
4643:cetrorelix
4599:bifluranol
4522:Nilutamide
4502:Bifluranol
4492:+niraparib
4436:inhibitors
4414:Nilutamide
4389:Cimetidine
4359:Oxendolone
4304:+niraparib
4298:Steroidal:
4166:norgestrel
4154:Progestins
4149:Gestrinone
4109:Mibolerone
4094:Stanozolol
3823:Quinbolone
2594:: 981684.
1954:9 November
1850:3 November
1818:8 November
1661:References
1521:Nilutamide
1483:nilutamide
1462:. It is a
1440:See also:
1399:. A major
1375:metabolite
1357:and mean (
1109:substrates
1022:estrogenic
968:including
845:antagonist
698:3D model (
686:Molar mass
537:4T36H88UA7
508:ChemSpider
436:CAS Number
415:IUPAC name
333:Metabolism
184:Drug class
9083:Thioureas
9073:Pyridines
8920:SKF-97541
8915:SCH-50911
8905:Phaclofen
8890:CGP-64213
8885:CGP-55845
8880:CGP-54626
8875:CGP-52432
8870:CGP-46381
8865:CGP-35348
8835:CGP-13501
8810:ADX-71441
8795:Tolgabide
8775:Progabide
8770:Picamilon
8755:Isovaline
8672:Agonists:
8574:-3-ACPBPA
8551:SKF-97541
8501:-3-ACPBPA
8428:Tolgabide
8408:Progabide
8403:Picamilon
8347:Agonists:
8255:RO4938581
8250:RO4882224
8177:flutamide
8111:L-655,708
8081:Flurothyl
7982:Cicutoxin
7967:Bupropion
7934:Bemegride
7911:β-Lactams
7901:Amiloride
7731:Volatiles
7665:etazolate
7641:Phenytoin
7599:zopiclone
7591:abecarnil
7550:Monastrol
7540:Lanthanum
7524:etomidate
7486:Fenamates
7481:Etifoxine
7476:Etazepine
7353:Tolgabide
7303:Progabide
7293:Picamilon
7278:Org 20599
7253:Monastrol
7233:L-838,417
7130:Agonists:
6974:-arginine
6959:Estradiol
6939:strontium
6935:magnesium
6923:aluminium
6890:YM-175735
6825:Ro 5-2537
6820:Ro 2-7239
6770:PF-998425
6765:Pentomone
6706:LG-120907
6666:Flutamide
6661:Fenarimol
6601:CH5137291
6540:Bakuchiol
6476:Topterone
6441:Prorenone
6416:Osaterone
6411:Nordinone
6396:Mexrenone
6316:Dienogest
6266:Canrenone
6187:TFM-4AS-1
6127:ORM-11984
6067:GSK-4336A
6057:GLPG-0492
5981:ZM-182345
5828:Gestodene
5816:Etynodiol
5572:Furazabol
5463:Enestebol
5391:Trendione
5352:Oxabolone
5278:Dienolone
5251:Bolandiol
5180:Nisterime
4934:Clostebol
4917:Boldenone
4733:Phase III
4721:Withdrawn
4607:estradiol
4595:Estrogens
4589:sulpiride
4567:) (e.g.,
4512:Flutamide
4404:Flutamide
4329:Dienogest
4309:Canrenone
4220:clomifene
4216:tamoxifen
4069:Furazabol
3783:Clostebol
3734:Androgens
3722:Androgens
3595:16 August
3585:Drugs.com
3520:0923-7534
3479:0923-7534
3002:: 12007.
2857:247777754
2813:235481675
2564:2212-7070
2091:16 August
1679:Drugs.com
1613:phase III
1507:Flutamide
1487:flutamide
1436:Chemistry
1414:clearance
1326:The mean
1238:induction
1159:selective
1053:flutamide
1038:estradiol
1016:. It may
1014:pregnancy
1006:teratogen
934:pregnancy
889:indicated
857:androgens
827:, and an
389:Excretion
374:half-life
170:Routes of
144:Pregnancy
92:Monograph
86:Drugs.com
9053:Nitriles
8997:Medicine
8946:See also
8910:Saclofen
8845:rac-BHFF
8840:GS-39783
8830:CGP-7930
8790:SL 75102
8765:Phenibut
8720:Gabamide
8705:Baclofen
8608:picrotin
8561:SR-95813
8556:SR-95318
8478:2-MeTACA
8390:Muscimol
8320:ZK-93426
8290:TCS-1105
8275:TB-21007
8206:picrotin
8146:Naloxone
8131:Morphine
8126:MaxiPost
8046:fipronil
8042:Fiproles
8012:(+)-DMBB
8007:Dieldrin
7906:Anisatin
7821:SR-42641
7721:Valerian
7695:baicalin
7691:Skullcap
7635:propofol
7615:zaleplon
7607:zolpidem
7500:apigenin
7420:diazepam
7377:Alcohols
7318:SL-75102
7308:Propofol
7288:Phenibut
7258:Muscimol
7242:honokiol
7208:iso-THIP
7203:iso-THAZ
7178:Gabamide
7094:receptor
7025:See also
6912:Agonists
6885:YM-92088
6850:RU-58841
6845:RU-58642
6840:RU-57073
6835:RU-56187
6830:RU-22930
6760:ONC1-13B
6711:LGD-1331
6636:Dieldrin
6630:p,p’-DDE
6535:AZD-3514
6520:Arabilin
6451:RU-15328
6391:Metogest
6326:DU-41165
6162:S-101479
6142:RU-59063
6097:LGD-4033
6092:LGD-3303
6082:LGD-2226
6072:GSK-8698
5971:Drupanol
5966:Cl-4AS-1
5906:Tibolone
5087:Bolazine
4830:Agonists
4745:See also
4651:(incl.,
4558:receptor
4184:Tibolone
3865:Sustanon
3861:Omnadren
3762:agonists
3684:29695920
3589:Archived
3552:Archived
3415:24002508
3364:Archived
3332:Archived
3307:23228778
3299:20853390
3264:19359544
3207:29912565
3199:15509184
3153:Archived
3132:24494031
3083:26313416
3034:26137992
2977:24019330
2928:23779130
2849:35349180
2805:34144936
2770:35509772
2713:12603397
2672:24100689
2620:23819055
2516:25236176
2472:23337756
2412:Archived
2385:22266222
2319:46925616
2311:29856649
2273:23355790
2221:22852027
2153:29626324
2085:Archived
2081:Medscape
2008:24002508
1948:Archived
1914:17 April
1908:Archived
1876:Archived
1841:Archived
1812:Archived
1808:DailyMed
1683:Archived
1535:RU-59063
1475:RU-59063
1422:excreted
1345:levels.
1328:absolute
1309:seizures
1292:in vitro
1288:receptor
1280:inhibits
1207:affinity
1203:seizures
1093:toxicity
1089:overdose
1085:antidote
1079:Overdose
1071:of rare
1002:seizures
982:diarrhea
962:surgical
938:seizures
914:and the
869:hormones
833:seizures
809:diarrhea
787:by mouth
517:28424131
488:DrugBank
477:24872560
196:ATC code
177:By mouth
146:category
128:DailyMed
9048:Lactams
8815:BHF-177
8800:Tolibut
8710:BL-1020
8623:ROD-188
8488:4-ACPAM
8483:3-APMPA
8350:BL-1020
8310:U-93631
8305:Thujone
8230:PWZ-029
8204:(i.e.,
8163:(e.g.,
8141:MRK-016
8121:Lindane
8073:(e.g.,
8054:(e.g.,
8044:(e.g.,
7913:(e.g.,
7891:β-EMGBL
7801:PHP-501
7737:(e.g.,
7708:(e.g.,
7686:ROD-188
7673:(e.g.,
7663:(e.g.,
7648:(e.g.,
7633:(e.g.,
7631:Phenols
7613:(e.g.,
7605:(e.g.,
7597:(e.g.,
7589:(e.g.,
7585:(e.g.,
7557:(e.g.,
7522:(e.g.,
7498:(e.g.,
7488:(e.g.,
7468:(e.g.,
7438:(e.g.,
7426:Bromide
7418:(e.g.,
7408:(e.g.,
7398:(e.g.,
7379:(e.g.,
7372:α-EMTBL
7342:borneol
7340:(e.g.,
7323:Taurine
7270:(e.g.,
7240:(e.g.,
7238:Lignans
7158:BL-1020
7145:(e.g.,
6981:-lysine
6969:(incl.
6927:calcium
6921:(incl.
6919:Cations
6716:Linuron
6656:EPI-001
6562:(e.g.,
6351:EM-6537
6346:EM-5855
6341:EM-5854
6336:EM-4350
6182:MK-0773
6177:EM-9017
6157:S-40503
6012:ACP-105
6007:198RL26
5872:(e.g.,
5845:(e.g.,
5754:Danazol
5704:RU-2309
5644:Bolenol
4641:(e.g.,
4631:(e.g.,
4597:(e.g.,
4242:(e.g.,
4228:(e.g.,
4214:(e.g.,
4156:(e.g.,
4144:Danazol
3942:(e.g.,
3835:(e.g.,
3737:(incl.
3675:5905496
3406:3782148
3255:2981508
3234:Bibcode
3226:Science
3123:3909768
3074:4673554
3025:4490394
3004:Bibcode
2968:3800038
2761:9057741
2721:8639102
2691:BJU Int
2663:3928129
2611:3684034
2524:6309403
2463:3788593
2376:3306502
2264:3553559
2212:3398601
2161:4653827
1999:3782148
1882:2 April
1606:phase I
1584:History
1464:pyridyl
1405:enzymes
1387:in the
1273:OATP1B1
1253:CYP2C19
1245:enzymes
1187:to the
1167:of the
1133:OATP1B1
1113:CYP2C19
970:fatigue
871:in the
847:of the
797:fatigue
771:Erleada
644:Formula
497:DB11901
463:PubChem
251::
212:)
206: (
204:L02BB05
159: D
133:Erleada
130::
106:a618018
18:Erleada
8983:Portal
8850:KK-92A
8680:3-APPA
8448:ATHDOC
8002:DHEA-S
7841:1,3M1B
7573:Niacin
7534:kavain
6904:GPRC6A
6880:YM-580
6810:RD-162
6701:LG-105
6052:FTBU-1
4716:WHO-EM
4683:Others
4482:Others
3682:
3672:
3518:
3477:
3413:
3403:
3360:
3305:
3297:
3262:
3252:
3205:
3197:
3130:
3120:
3081:
3071:
3032:
3022:
2975:
2965:
2926:
2880:
2855:
2847:
2811:
2803:
2768:
2758:
2719:
2711:
2670:
2660:
2618:
2608:
2562:
2522:
2514:
2494:Cancer
2470:
2460:
2408:
2383:
2373:
2317:
2309:
2271:
2261:
2219:
2209:
2159:
2151:
2006:
1996:
1563:RD-162
1468:RD-162
1460:RD-162
1397:CYP3A4
1393:CYP2C8
1271:, and
1257:CYP2C9
1249:CYP3A4
1117:CYP2C9
1032:, and
996:, and
980:, and
974:nausea
851:, the
801:nausea
724:SMILES
691:477.44
568:ChEMBL
557:D11040
346:CYP3A4
342:CYP2C8
278:℞-only
276:
263:
253:℞-only
239:
126:
8740:GHBAL
8725:GABOB
8628:THDOC
8572:trans
8566:TPMPA
8541:P4MPA
8493:4-GBA
8375:GABOB
8101:IPTBO
7951:IPTBO
7886:β-CCP
7881:β-CCM
7876:β-CCE
7871:β-CCB
7831:Tutin
7735:gases
7567:THDOC
7183:GABOB
6568:BFDGE
6564:BADGE
6510:AA560
6192:YK-11
6102:LY305
5992:SARMs
3621:(1).
3303:S2CID
3203:S2CID
3156:(PDF)
3149:(PDF)
2853:S2CID
2809:S2CID
2717:S2CID
2520:S2CID
2315:S2CID
2157:S2CID
2133:Drugs
1944:(EMA)
1844:(PDF)
1837:(PDF)
1481:NSAA
1430:feces
1426:urine
1389:liver
1269:ABCG2
1131:, or
1129:ABCG2
1051:like
990:falls
859:like
821:falls
744:InChI
700:JSmol
401:: 24%
399:Feces
396:: 65%
394:Urine
338:Liver
327:: 95%
8958:GABA
8895:DAVA
8825:BSPP
8820:BHFF
8715:GABA
8657:GABA
8633:Zinc
8579:ZAPA
8526:I4AA
8511:DAVA
8418:TAMP
8413:TACA
8370:GABA
8360:CAMP
8355:CACA
8331:GABA
8315:Zinc
8300:TETS
8285:TBPS
8280:TBOB
8212:and
8027:EBOB
8022:DMPC
8017:DMCM
7997:DHEA
7972:CHEB
7957:BIDN
7947:TBPO
7943:TBPS
7861:α3IA
7846:3M2B
7530:Kava
7385:2M2B
7367:here
7358:ZAPA
7333:TAMP
7328:TACA
7173:GABA
7163:DAVA
7115:GABA
7092:GABA
7000:SHBG
6943:zinc
6641:DIMP
6256:BOMT
6152:S-23
6042:DTIB
3724:and
3680:PMID
3597:2024
3560:2018
3534:link
3516:ISSN
3475:ISSN
3411:PMID
3340:2015
3295:PMID
3260:PMID
3195:PMID
3164:2018
3128:PMID
3079:PMID
3030:PMID
2973:PMID
2924:PMID
2878:ISBN
2845:PMID
2801:PMID
2766:PMID
2709:PMID
2668:PMID
2616:PMID
2592:2013
2560:ISSN
2512:PMID
2468:PMID
2381:PMID
2307:PMID
2269:PMID
2217:PMID
2149:PMID
2093:2024
2049:2018
2004:PMID
1956:2020
1916:2024
1884:2024
1852:2022
1820:2020
1691:2020
1458:and
1444:and
1395:and
1331:oral
1284:GABA
1282:the
1251:and
1213:, a
1183:and
1087:for
1063:and
1055:and
992:and
986:rash
863:and
817:rash
548:KEGG
528:UNII
361:NDMA
325:NDMA
312:100%
302:data
82:AHFS
8750:GVL
8745:GHV
8735:GHB
8730:GBL
8546:P4S
8499:cis
8265:SCS
7609:),
7601:),
7593:),
7298:P4S
6626:DDT
6147:S-1
6137:R-1
4254:hCG
3740:AAS
3670:PMC
3660:doi
3623:hdl
3506:doi
3465:doi
3434:doi
3401:PMC
3393:doi
3287:doi
3250:PMC
3242:doi
3230:324
3187:doi
3118:PMC
3110:doi
3069:PMC
3061:doi
3020:PMC
3012:doi
2963:PMC
2955:doi
2914:doi
2837:doi
2793:doi
2756:PMC
2748:doi
2699:doi
2658:PMC
2650:doi
2606:PMC
2596:doi
2552:doi
2502:doi
2498:121
2458:PMC
2450:doi
2371:PMC
2363:doi
2299:doi
2259:PMC
2251:doi
2207:PMC
2199:doi
2141:doi
1994:PMC
1986:doi
1454:of
1424:in
1391:by
964:or
952:in
898:or
855:of
593:EPA
467:CID
265:POM
209:WHO
9009::
8610:,
8335:-ρ
8208:,
8179:,
8175:,
8171:,
8167:,
8058:,
7949:,
7945:,
7921:,
7917:,
7753:,
7749:,
7745:,
7741:,
7617:))
7565:,
7561:,
7502:,
7383:,
6983:,
6976:,
6941:,
6937:,
6933:,
6929:,
6925:,
6578:,
6574:,
6570:,
6566:,
5876:,
5531:)
5120:)
5021:)
4818:AR
4729::
4671:,
4667:,
4663:,
4659:,
4655:,
4621:,
4617:,
4613:,
4609:,
4605:,
4601:,
4587:,
4583:,
4579:,
4575:,
4571:,
4283:AR
4251:,
4245:LH
4232:,
4218:,
4176:,
4172:,
4168:,
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4160:,
3946:,
3871:))
3867:,
3863:,
3859:,
3851:,
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284:EU
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