1041:, where the amine group is converted to an imine by deprotonation, then attacks the free aldehyde to form a carbocation that is quenched by electrons from the methyl-phenol ring. This is done in the EtuA2 T-domain. This reaction is done a second time to yield a dimer of modified tyrosine residues that have been further cyclized via Pictet-Spengler reaction, yielding a bicyclic ring moiety. The EtuO and EtuF3 enzymes continue to post-translationally modify the molecule, adding several functional groups and making a sulfide bridge between the original cysteine residue and the beta-carbon of the first tyrosine to form ET-583, ET-597, ET-596, and ET-594 which have been previously isolated. A third
691:
668:
1019:
31:
949:. However, the pivotal study did show a significant difference between two different trabectedin treatment regimens, and due to the rarity of the disease, the CHMP considered that marketing authorization could be granted under exceptional circumstances. As part of the approval PharmaMar agreed to conduct a further trial to identify whether any specific chromosomal
3680:
763:
1446:
901:
licensed the compound from the
University of Illinois before 1994 and attempted to farm the sea squirt with limited success. Yields from the sea squirt are extremely low as around 1,000 kilograms of animals is needed to isolate 1 gram of trabectedin - and about 5 grams were believed to be
892:
was found to have anticancer activity in 1969. Separation and characterization of the active molecules had to wait many years for the development of sufficiently sensitive techniques, and the structure of one of them, Ecteinascidin 743, was determined by KL Rinehart at the
University of Illinois in
906:
to search for a synthetic method of preparation. His group developed such a method and published it in 1996. This was later followed by a simpler and more tractable method which was patented by
Harvard and subsequently licensed to PharmaMar. The current supply is based on a semisynthetic process
1121:
work that this binding occurs in the minor groove, spans approximately three to five base pairs and is most efficient with CGG sequences. Additional favorable binding sequences are TGG, AGC, or GGC. Once bound, this reversible covalent adduct bends DNA toward the major groove, interferes directly
1036:
starts with a fatty acid loading onto the acyl-ligase domain of the EtuA3 module. A cysteine and glycine are then loaded as canonical NRPS amino acids. A tyrosine residue is modified by the enzymes EtuH, EtuM1, and EtuM2 to add a hydroxyl at the meta position of the phenol, and adding two methyl
805:
InChI=1S/C39H43N3O11S/c1-16-9-20-10-22-37(46)42-23-13-50-38(47)39(21-12-25(48-5)24(44)11-19(21)7-8-40-39)14-54-36(30(42)29(41(22)4)26(20)31(45)32(16)49-6)28-27(23)35-34(51-15-52-35)17(2)33(28)53-18(3)43/h9,11-12,22-23,29-30,36-37,40,44-46H,7-8,10,13-15H2,1-6H3/t22-,23-,29+,30+,36+,37-,39+/m0/s1
941:(CHMP), observed that trabectedin had not been evaluated in an adequately designed and analyzed randomized controlled trial against current best care, and that the clinical efficacy data were mainly based on patients with
1116:
Other than transcriptional interference, the mechanism of action of trabectedin is complex and not completely understood. The compound is known to bind and alkylate DNA at the N2 position of guanine. It is known from
1865:
Son K, Takhaveev V, Mor V, Yu H, Dillier E, Zilio N, et al. (February 2024). "Trabectedin derails transcription-coupled nucleotide excision repair to induce DNA breaks in highly transcribed genes".
967:
approved trabectedin (Yondelis) for the treatment of liposarcoma and leiomyosarcoma that is either unresectable or has metastasized. Patients must have received prior chemotherapy with an anthracycline.
929:
In 2007, the
European Commission gave authorization for the marketing of trabectedin, under the trade name Yondelis, "for the treatment of patients with advanced soft tissue sarcoma, after failure of
1447:"Hostages of the deep - Prospectors are taking to the seas in search of new and promising chemicals. But the better the drugs turn out to be, the greater the threat to the animals that produce them"
988:. In 2011, Johnson & Johnson voluntarily withdrew the submission in the United States following a request by the FDA for an additional phase III study to be done in support of the submission.
289:
893:
1984. Rinehart had collected his sea squirts by scuba diving in the reefs of the West Indies. The biosynthetic pathway responsible for producing the drug has been determined to come from
1494:
Cuevas C, Pérez M, Martín MJ, Chicharro JL, Fernández-Rivas C, Flores M, et al. (August 2000). "Synthesis of ecteinascidin ET-743 and phthalascidin Pt-650 from cyanosafracin B".
859:
It is sold by Pharma Mar S.A. and
Johnson and Johnson. It is approved for use in the European Union, Russia, South Korea and the United States. The European Commission and the U.S.
1641:
1094:
to assist in the formation of the pentacyclic core. This reaction was unprecedented for using such a one pot multicomponent reaction in the synthesis of such a complex molecule.
244:
821:
1619:
1134:
1958:
1674:
1138:
1123:
3720:
1113:. By reversing the genetic program created by this transcription factor, trabectedin promotes differentiation and reverses the oncogenic phenotype in these cells.
938:
1529:
1575:
125:
2658:
777:
856:
The most common adverse reactions include nausea, fatigue, vomiting, constipation, decreased appetite, diarrhea, peripheral edema, dyspnea, and headache.
176:
1558:
3700:
3634:
1951:
1778:
1301:
Lichter W, Wallham LL, Van Der Worf BA, Middle Brook RE, Sigal MM, Weinheimer AJ (August 1972). Worthen LW (ed.). "Food Drugs from the Sea".
1369:
3241:
2393:
2349:
2227:
1649:
1398:"Meta-omic characterization of the marine invertebrate microbial consortium that produces the chemotherapeutic natural product ET-743"
1162:
In
September 2020, the European Medicines Agency recommended that the use of trabectedin in treating ovarian cancer remain unchanged.
3740:
2152:
797:
93:
1627:
1333:
1944:
1239:
1149:
incision at trabectedin lesions, recording TC-NER on a genome-wide scale, which resulted in a TC-NER-profiling assay TRABI-Seq.
2874:
2668:
413:
274:
157:
1696:
1664:
1141:
of trabectedin-DNA adducts forms persistent single-strand breaks (SSBs) as the adducts block the second of the two sequential
883:
carried out a wide-ranging program of screening plant and marine organism material. As part of that program, extract from the
3287:
2289:
2179:
449:)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydrospiroisoquinobenzazocine-20,1'(2'
1057:
by E.J. Corey used this proposed biosynthesis to guide their synthetic strategy. The synthesis uses such reactions as the
3710:
3209:
3192:
3067:
2831:
2209:
1037:
groups at the para-hydroxyl and the meta carbon position. This modified tyrosine reacts with the original substrate via a
3670:
3745:
2941:
2537:
860:
567:
193:
3651:
3143:
1936:
647:
1579:
2323:
1146:
1142:
3509:
3389:
3379:
1916:
1277:
977:
880:
171:
3735:
3561:
3494:
3464:
3082:
2332:
1062:
1038:
516:
3705:
3639:
3546:
3364:
3079:
2565:
2413:
2340:
1209:"Yondelis 1 mg powder for concentrate for solution for infusion - Summary of Product Characteristics (SmPC)"
909:
888:
230:
1718:
D'Incalci M, Galmarini CM (August 2010). "A review of trabectedin (ET-743): a unique mechanism of action".
686:
3715:
3444:
3434:
3167:
3009:
1669:
1000:
355:
937:, or who are unsuited to receive these agents". The European Medicine Agency's evaluating committee, the
913:. PharmaMar entered into an agreement with Johnson & Johnson to market the compound outside Europe.
636:
3725:
2716:
2533:
2503:
2363:
1070:
1066:
507:
907:
developed by PharmaMar starting from safracin B, a chemical obtained by fermentation of the bacterium
3114:
2991:
2512:
2428:
1103:
382:
3399:
3299:
3278:
2999:
2821:
2653:
2384:
2280:
1593:
846:
663:
462:
237:
1911:
2457:
1743:
1345:
1110:
204:
3606:
2487:
2467:
2452:
1377:
3581:
3155:
1989:
1893:
1846:
1794:
1774:
1735:
1511:
1427:
1337:
903:
616:
315:
302:
107:
1272:
785:
Cc1cc2c(c(c1OC)O)345c6c(c7c(c(c6OC(=O)C)C)OCO7)(N4((C2)N3C)O)COC(=O)8(CS5)c9cc(c(cc9CCN8)O)OC
3730:
3586:
3343:
3058:
2692:
2677:
2398:
1883:
1875:
1836:
1828:
1784:
1766:
1727:
1503:
1476:
1467:
Corey EJ, Gin DY, Kania RS (1996). "Enantioselective Total
Synthesis of Ecteinascidin 743".
1417:
1409:
1329:
1145:
incisions. The researchers mapped the 3’-hydroxyl groups of SSBs originating from the first
1126:
complex, promotes degradation of RNA polymerase II, and generates DNA double-strand breaks.
1084:
1058:
1003:
703:
471:
337:
48:
1815:
Grohar PJ, Griffin LB, Yeung C, Chen QR, Pommier Y, Khanna C, et al. (February 2011).
1045:-methylated tyrosine is added and cyclized via Pictet-Spengler to yield the final product.
576:
556:
3684:
3025:
2987:
2778:
2200:
2115:
1054:
1018:
897:
Endoecteinascidia frumentensis, a microbial symbiont of the tunicate. The
Spanish company
365:
345:
1761:
Chukwueke UN, Wen PY (2020). "Medical management of meningiomas". In McDermott MW (ed.).
690:
667:
3645:
3179:
2770:
2264:
2128:
2015:
1985:
1972:
1841:
1816:
1789:
1770:
1422:
1397:
985:
950:
946:
868:
850:
1208:
30:
3694:
3519:
3479:
2849:
2722:
2603:
2546:
2304:
2253:
1087:
991:
Trabectedin is also in phase II trials for prostate, breast, and paediatric cancers.
930:
679:
149:
1349:
3566:
3530:
3414:
3404:
3358:
3354:
3316:
3224:
3014:
2953:
2949:
2930:
2925:
2904:
2893:
2707:
2701:
2687:
2682:
2613:
2608:
2561:
2447:
2314:
2294:
2223:
2172:
2162:
1976:
1968:
1817:"Ecteinascidin 743 interferes with the activity of EWS-FLI1 in Ewing sarcoma cells"
1747:
1704:
1091:
1077:
496:
257:
252:
135:
1731:
1396:
Rath CM, Janto B, Earl J, Ahmed A, Hu FZ, Hiller L, et al. (November 2011).
1102:
Recently, it has been shown that trabectedin blocks DNA binding of the oncogenic
3611:
3576:
3571:
3556:
3514:
3484:
3424:
3394:
3338:
3311:
3184:
3125:
3097:
3087:
3040:
3004:
2920:
2882:
2864:
2859:
2839:
2816:
2787:
2765:
2745:
2735:
2586:
2571:
2551:
2437:
2368:
2354:
2309:
2242:
2237:
2214:
2189:
2157:
2100:
2063:
2040:
2025:
2020:
2005:
981:
960:
942:
864:
143:
1888:
1879:
3601:
3504:
3499:
3474:
3469:
3459:
3454:
3449:
3419:
3409:
3374:
3369:
3349:
3304:
3292:
3267:
3262:
3252:
3234:
3229:
3219:
3214:
3172:
3160:
3148:
3120:
3107:
3102:
3072:
3035:
3030:
2968:
2963:
2909:
2854:
2806:
2792:
2740:
2727:
2696:
2629:
2618:
2591:
2581:
2576:
2522:
2477:
2472:
2373:
2337:
2269:
2259:
2248:
2232:
2184:
2167:
2143:
2095:
2083:
2035:
1182:
1130:
934:
739:
547:
1765:. Handbook of Clinical Neurology. Vol. 170. Elsevier. pp. 291–302.
3616:
3596:
3551:
3541:
3535:
3439:
3384:
3333:
3257:
3247:
3202:
3189:
3130:
3092:
3020:
2958:
2899:
2888:
2844:
2801:
2760:
2754:
2750:
2712:
2639:
2634:
2624:
2596:
2556:
2517:
2492:
2482:
2442:
2088:
2078:
2073:
2068:
2030:
1081:
1027:
898:
395:
129:
22:
1897:
1850:
1798:
1739:
1515:
1431:
1341:
3525:
3489:
3429:
3197:
3135:
2915:
2811:
2783:
2462:
2299:
1106:
1007:
884:
527:
188:
845:, is an antitumor chemotherapy medication for the treatment of advanced
536:
2418:
2319:
2133:
1994:
1832:
1073:
1006:, eight rings including one 10-membered heterocyclic ring containing a
976:
In 2008, the submission was announced of a registration dossier to the
482:
1642:"FDA Approves Trabectedin (Yondelis) for Advanced Soft-Tissue Sarcoma"
1507:
1480:
1413:
1334:
10.1002/(SICI)1098-1128(200001)20:1<1::AID-MED1>3.0.CO;2-A
2058:
1620:"Trabectedin Superior to Dacarbazine for Leiomyosarcoma, Liposarcoma"
964:
627:
374:
1240:"Yondelis- trabectedin injection, powder, lyophilized, for solution"
596:
1320:
Rinehart KL (January 2000). "Antitumor compounds from tunicates".
1017:
902:
needed for a clinical trial so
Rinehart asked the Harvard chemist
762:
753:
607:
370:
587:
321:
296:
175:
166:
1940:
980:
and the FDA for
Yondelis when administered in combination with
309:
183:
959:
In 2015, (after a phase III study comparing trabectedin with
652:
283:
215:
66:
57:
984:(Doxil, Caelyx) for the treatment of women with relapsed
81:
75:
1370:"Potent cancer drugs made -- Sea squirts provide recipe"
956:
Trabectedin is also approved in South Korea and Russia.
953:
could be used to predict responsiveness to trabectedin.
828:
1177:
1175:
3668:
94:
84:
69:
1234:
1232:
1230:
78:
72:
63:
54:
51:
3326:
3277:
3057:
3050:
2986:
2940:
2873:
2830:
2667:
2652:
2532:
2502:
2427:
2412:
2383:
2279:
2199:
2142:
2125:
2114:
2050:
2003:
1984:
867:status to trabectedin for soft-tissue sarcomas and
751:
738:
702:
697:
678:
646:
626:
606:
586:
566:
546:
526:
515:
506:
481:
461:
404:
394:
381:
364:
354:
344:
336:
273:
268:
243:
229:
203:
156:
142:
124:
116:
106:
60:
42:
37:
1090:. A separate synthetic process also involved the
921:Trabectedin was first trialed in humans in 1996.
1665:"J&J pulls submission for Zeltia's Yondelis"
1139:transcription-coupled nucleotide excision repair
1124:transcription-coupled nucleotide excision repair
1026:The biosynthesis of trabectedin in the tunicate
1022:Proposed scheme for the biosynthesis of the drug
495:
1267:
1265:
1263:
1261:
470:
1594:"S.Korea approves Zeltia cancer drug Yondelis"
1539:. European Medicines Agency. 24 September 2009
1537:Post-Authorization Summary of Positive Opinion
1391:
1389:
1387:
939:Committee for Medicinal Products for Human Use
1952:
1810:
1808:
8:
1109:and reverses the transcriptional program in
192:
21:
329:In general: ℞ (Prescription only)
3054:
2664:
2424:
2139:
2122:
2000:
1959:
1945:
1937:
1122:with activated transcription, poisons the
689:
666:
555:
29:
1887:
1840:
1788:
1421:
1363:
1361:
1359:
575:
3721:Drugs developed by Johnson & Johnson
1469:Journal of the American Chemical Society
1462:
1460:
3675:
1673:. London, England. Online PharmaTimes.
1171:
802:
782:
662:
535:
418:
148:
1187:Therapeutic Goods Administration (TGA)
680:
20:
635:
615:
134:
7:
256:
2228:ribonucleotide reductase inhibitors
1677:from the original on 2 October 2011
1626:. 21 September 2015. Archived from
1010:residue, and seven chiral centers.
595:
486:
2394:Ribonucleotide reductase inhibitor
2350:Ribonucleotide reductase inhibitor
1771:10.1016/B978-0-12-822198-3.00048-3
14:
2153:Dihydrofolate reductase inhibitor
1648:. 26 October 2015. Archived from
999:Trabectedin is composed of three
3678:
879:During the 1950s and 1960s, the
720:
714:
47:
982:pegylated liposomal doxorubicin
810:Key:PKVRCIRHQMSYJX-AIFWHQITSA-N
2290:Thymidylate synthase inhibitor
2180:Thymidylate synthase inhibitor
1034:Endoecteinascidia frumentensis
732:
726:
708:
1:
2210:Adenosine deaminase inhibitor
2051:Block microtubule disassembly
1732:10.1158/1535-7163.MCT-10-0263
1720:Molecular Cancer Therapeutics
3701:2,5-Dimethoxyphenethylamines
1445:Pain S (14 September 1996).
861:Food and Drug Administration
841:, sold under the brand name
1309:. Marine Tech Soc: 117–127.
453:)-isoquinolin]-5-yl acetate
3762:
1880:10.1038/s41467-024-45664-7
1374:Harvard University Gazette
1322:Medicinal Research Reviews
1129:In 2024, researchers from
698:Chemical and physical data
3629:
3510:Omacetaxine mepesuccinate
3390:Ciltacabtagene autoleucel
3380:Brexucabtagene autoleucel
1917:European Medicines Agency
1278:European Medicines Agency
1137:determined that abortive
978:European Medicines Agency
917:Approvals and indications
881:National Cancer Institute
818:
793:
773:
409:
120:ecteinascidin 743, ET-743
28:
3741:Phenethylamine alkaloids
3562:Talimogene laherparepvec
3495:Nadofaragene firadenovec
3465:Lisocabtagene maraleucel
2414:Topoisomerase inhibitors
2333:DNA polymerase inhibitor
1855:and works cited therein.
1697:"Yondelis (trabectedin)"
1530:"YONDELIS (trabectedin)"
1368:Cromie WJ (4 May 2000).
1063:Pictet-Spengler reaction
1039:Pictet-Spengler reaction
972:Ovarian cancer and other
875:Discovery and production
350:Not applicable (IV only)
3365:Axicabtagene ciloleucel
1969:chemotherapeutic agents
1663:Grogan K (3 May 2011).
910:Pseudomonas fluorescens
889:Ecteinascidia turbinata
3547:Sitimagene ceradenovec
3445:Idecabtagene vicleucel
3010:Methyl aminolevulinate
1582:on September 18, 2008.
1023:
1001:tetrahydroisoquinoline
3021:Porphyrin derivatives
2717:Melphalan flufenamide
2364:Hypomethylating agent
1973:antineoplastic agents
1868:Nature Communications
1067:Curtius rearrangement
1021:
3711:Antineoplastic drugs
3350:Asparagine depleters
3279:Receptor antagonists
3193:+abiraterone acetate
1763:Meningiomas, Part II
1707:on 13 February 2012.
1670:PharmaTimes Magazine
1402:ACS Chemical Biology
1104:transcription factor
3746:Bacterial alkaloids
3400:Denileukin diftitox
3300:Retinoid X receptor
3000:Aminolevulinic acid
2822:Triethylenemelamine
2654:Crosslinking of DNA
2385:Deoxyribonucleotide
2324:+gimeracil/oteracil
1889:20.500.11850/661709
1576:"PharmaMar website"
1282:. 17 September 2018
1246:. 22 September 2020
1215:. 21 September 2020
1153:Society and culture
1098:Mechanism of action
925:Soft tissue sarcoma
847:soft-tissue sarcoma
305:(Prescription only)
292:(Prescription only)
25:
3656:Never to phase III
2458:Etirinotecan pegol
1921:. 27 February 2020
1833:10.1593/neo.101202
1111:myxoid liposarcoma
1028:symbiotic bacteria
1024:
3666:
3665:
3625:
3624:
3582:Tigilanol tiglate
3059:Enzyme inhibitors
2982:
2981:
2978:
2977:
2678:Nitrogen mustards
2648:
2647:
2408:
2407:
2110:
2109:
1780:978-0-12-822198-3
1652:on 17 March 2016.
1559:"CHMP evaluation"
1508:10.1021/ol0062502
1502:(16): 2545–2548.
1481:10.1021/ja962480t
1475:(38): 9202–9203.
1414:10.1021/cb200244t
1408:(11): 1244–1256.
836:
835:
764:Interactive image
648:CompTox Dashboard
325:
313:
300:
287:
219:
186:
169:
16:Chemical compound
3753:
3683:
3682:
3681:
3674:
3587:Tisagenlecleucel
3344:Arsenic trioxide
3055:
2988:Photosensitizers
2779:Alkyl sulfonates
2693:Cyclophosphamide
2665:
2604:Anthracenediones
2425:
2399:Hydroxycarbamide
2140:
2123:
2001:
1961:
1954:
1947:
1938:
1931:
1930:
1928:
1926:
1908:
1902:
1901:
1891:
1862:
1856:
1854:
1844:
1812:
1803:
1802:
1792:
1758:
1752:
1751:
1726:(8): 2157–2163.
1715:
1709:
1708:
1703:. Archived from
1693:
1687:
1686:
1684:
1682:
1660:
1654:
1653:
1638:
1632:
1631:
1630:on 5 March 2016.
1616:
1610:
1609:
1607:
1605:
1590:
1584:
1583:
1578:. Archived from
1572:
1566:
1565:
1563:
1555:
1549:
1548:
1546:
1544:
1534:
1526:
1520:
1519:
1491:
1485:
1484:
1464:
1455:
1454:
1442:
1436:
1435:
1425:
1393:
1382:
1381:
1376:. Archived from
1365:
1354:
1353:
1317:
1311:
1310:
1298:
1292:
1291:
1289:
1287:
1269:
1256:
1255:
1253:
1251:
1236:
1225:
1224:
1222:
1220:
1205:
1199:
1198:
1196:
1194:
1179:
1085:enantioselective
1059:Mannich reaction
832:
831:
824:
766:
746:
734:
728:
722:
716:
710:
693:
682:
671:
670:
656:
654:
639:
619:
599:
579:
559:
539:
519:
499:
489:
488:
474:
390:180 hours (mean)
386:
323:
320:
311:
308:
298:
295:
285:
282:
260:
217:
214:
196:
185:
182:
179:
168:
165:
152:
138:
98:
91:
90:
87:
86:
83:
80:
77:
74:
71:
68:
65:
62:
59:
56:
53:
33:
26:
24:
3761:
3760:
3756:
3755:
3754:
3752:
3751:
3750:
3736:Total synthesis
3691:
3690:
3689:
3679:
3677:
3669:
3667:
3662:
3661:
3646:Clinical trials
3621:
3327:Other/ungrouped
3322:
3273:
3046:
3026:Porfimer sodium
2974:
2936:
2869:
2826:
2656:
2644:
2528:
2498:
2416:
2404:
2379:
2275:
2195:
2131:
2129:antimetabolites
2127:
2126:DNA precursors/
2118:
2116:DNA replication
2106:
2046:
2016:Vinca alkaloids
1992:
1980:
1965:
1935:
1934:
1924:
1922:
1910:
1909:
1905:
1864:
1863:
1859:
1814:
1813:
1806:
1781:
1760:
1759:
1755:
1717:
1716:
1712:
1695:
1694:
1690:
1680:
1678:
1662:
1661:
1657:
1640:
1639:
1635:
1618:
1617:
1613:
1603:
1601:
1592:
1591:
1587:
1574:
1573:
1569:
1561:
1557:
1556:
1552:
1542:
1540:
1532:
1528:
1527:
1523:
1496:Organic Letters
1493:
1492:
1488:
1466:
1465:
1458:
1444:
1443:
1439:
1395:
1394:
1385:
1380:on 3 June 2006.
1367:
1366:
1357:
1319:
1318:
1314:
1300:
1299:
1295:
1285:
1283:
1273:"Yondelis EPAR"
1271:
1270:
1259:
1249:
1247:
1238:
1237:
1228:
1218:
1216:
1207:
1206:
1202:
1192:
1190:
1181:
1180:
1173:
1168:
1160:
1155:
1100:
1055:total synthesis
1051:
1049:Total synthesis
1016:
997:
974:
927:
919:
877:
827:
825:
822:(what is this?)
819:
814:
811:
806:
801:
800:
789:
786:
781:
780:
769:
744:
731:
725:
719:
713:
674:
650:
642:
622:
602:
582:
562:
542:
522:
502:
485:
477:
457:
454:
417:
416:
384:
356:Protein binding
346:Bioavailability
338:Pharmacokinetic
332:
264:
232:
225:
206:
199:
96:
92:
50:
46:
17:
12:
11:
5:
3759:
3757:
3749:
3748:
3743:
3738:
3733:
3728:
3723:
3718:
3713:
3708:
3706:Acetate esters
3703:
3693:
3692:
3688:
3687:
3664:
3663:
3660:
3659:
3658:
3657:
3654:
3643:
3637:
3631:
3630:
3627:
3626:
3623:
3622:
3620:
3619:
3614:
3609:
3604:
3599:
3594:
3589:
3584:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3539:
3533:
3522:
3517:
3512:
3507:
3502:
3497:
3492:
3487:
3482:
3477:
3472:
3467:
3462:
3457:
3452:
3447:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3382:
3377:
3372:
3367:
3362:
3346:
3341:
3336:
3330:
3328:
3324:
3323:
3321:
3320:
3308:
3296:
3283:
3281:
3275:
3274:
3272:
3271:
3265:
3260:
3255:
3250:
3238:
3232:
3227:
3222:
3217:
3206:
3200:
3195:
3187:
3180:PARP inhibitor
3176:
3164:
3152:
3140:
3139:
3138:
3133:
3128:
3123:
3111:
3105:
3100:
3095:
3090:
3076:
3063:
3061:
3052:
3048:
3047:
3045:
3044:
3038:
3033:
3028:
3017:
3012:
3007:
3002:
2996:
2994:
2984:
2983:
2980:
2979:
2976:
2975:
2973:
2972:
2966:
2961:
2956:
2946:
2944:
2938:
2937:
2935:
2934:
2928:
2923:
2912:
2907:
2902:
2897:
2885:
2879:
2877:
2871:
2870:
2868:
2867:
2862:
2857:
2852:
2847:
2842:
2836:
2834:
2832:Platinum-based
2828:
2827:
2825:
2824:
2819:
2814:
2809:
2797:
2796:
2790:
2774:
2773:
2768:
2763:
2758:
2748:
2743:
2731:
2730:
2725:
2720:
2710:
2705:
2699:
2690:
2685:
2673:
2671:
2662:
2650:
2649:
2646:
2645:
2643:
2642:
2637:
2632:
2627:
2622:
2616:
2611:
2600:
2594:
2589:
2584:
2579:
2574:
2569:
2559:
2554:
2547:Anthracyclines
2542:
2540:
2530:
2529:
2527:
2526:
2520:
2508:
2506:
2500:
2499:
2497:
2496:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2445:
2433:
2431:
2422:
2410:
2409:
2406:
2405:
2403:
2402:
2389:
2387:
2381:
2380:
2378:
2377:
2371:
2359:
2358:
2345:
2344:
2328:
2327:
2317:
2312:
2307:
2302:
2297:
2285:
2283:
2277:
2276:
2274:
2273:
2267:
2265:Mercaptopurine
2256:
2251:
2246:
2240:
2235:
2219:
2218:
2205:
2203:
2197:
2196:
2194:
2193:
2187:
2176:
2170:
2165:
2160:
2148:
2146:
2137:
2120:
2112:
2111:
2108:
2107:
2105:
2104:
2092:
2086:
2081:
2076:
2071:
2066:
2054:
2052:
2048:
2047:
2045:
2044:
2038:
2033:
2028:
2023:
2011:
2009:
1998:
1982:
1981:
1967:Intracellular
1966:
1964:
1963:
1956:
1949:
1941:
1933:
1932:
1903:
1857:
1827:(2): 145–153.
1804:
1779:
1753:
1710:
1688:
1655:
1646:Cancer Network
1633:
1624:Cancer Network
1611:
1585:
1567:
1550:
1521:
1486:
1456:
1437:
1383:
1355:
1312:
1293:
1257:
1226:
1200:
1170:
1169:
1167:
1164:
1159:
1156:
1154:
1151:
1099:
1096:
1050:
1047:
1015:
1012:
996:
993:
986:ovarian cancer
973:
970:
951:translocations
947:leiomyosarcoma
931:anthracyclines
926:
923:
918:
915:
876:
873:
869:ovarian cancer
863:(FDA) granted
851:ovarian cancer
834:
833:
816:
815:
813:
812:
809:
807:
804:
796:
795:
794:
791:
790:
788:
787:
784:
776:
775:
774:
771:
770:
768:
767:
759:
757:
749:
748:
742:
736:
735:
729:
723:
717:
711:
706:
700:
699:
695:
694:
684:
676:
675:
673:
672:
659:
657:
644:
643:
641:
640:
632:
630:
624:
623:
621:
620:
612:
610:
604:
603:
601:
600:
592:
590:
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:
479:
478:
476:
475:
467:
465:
459:
458:
456:
455:
420:
412:
411:
410:
407:
406:
402:
401:
398:
392:
391:
388:
379:
378:
368:
362:
361:
358:
352:
351:
348:
342:
341:
334:
333:
331:
330:
327:
318:
306:
293:
279:
277:
271:
270:
266:
265:
263:
262:
249:
247:
241:
240:
235:
233:administration
227:
226:
224:
223:
221:
211:
209:
201:
200:
198:
197:
180:
162:
160:
154:
153:
146:
140:
139:
132:
122:
121:
118:
114:
113:
110:
104:
103:
44:
40:
39:
35:
34:
15:
13:
10:
9:
6:
4:
3:
2:
3758:
3747:
3744:
3742:
3739:
3737:
3734:
3732:
3729:
3727:
3724:
3722:
3719:
3717:
3716:Benzodioxoles
3714:
3712:
3709:
3707:
3704:
3702:
3699:
3698:
3696:
3686:
3676:
3672:
3655:
3653:
3650:
3649:
3647:
3644:
3641:
3638:
3636:
3633:
3632:
3628:
3618:
3615:
3613:
3610:
3608:
3605:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3545:
3543:
3540:
3537:
3534:
3532:
3528:
3527:
3523:
3521:
3520:Tabelecleucel
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3491:
3488:
3486:
3483:
3481:
3480:Lurbinectedin
3478:
3476:
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3383:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3360:
3356:
3352:
3351:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3331:
3329:
3325:
3318:
3314:
3313:
3309:
3306:
3302:
3301:
3297:
3294:
3290:
3289:
3285:
3284:
3282:
3280:
3276:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3251:
3249:
3245:
3243:
3239:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3212:
3211:
3207:
3204:
3201:
3199:
3196:
3194:
3191:
3188:
3186:
3182:
3181:
3177:
3174:
3170:
3169:
3165:
3162:
3158:
3157:
3153:
3150:
3146:
3145:
3141:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3118:
3117:
3116:
3112:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3089:
3085:
3084:
3081:
3077:
3074:
3070:
3069:
3065:
3064:
3062:
3060:
3056:
3053:
3049:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3023:
3022:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2997:
2995:
2993:
2989:
2985:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2951:
2948:
2947:
2945:
2943:
2942:Intercalation
2939:
2932:
2929:
2927:
2924:
2922:
2918:
2917:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2895:
2891:
2890:
2886:
2884:
2881:
2880:
2878:
2876:
2872:
2866:
2863:
2861:
2858:
2856:
2853:
2851:
2850:Dicycloplatin
2848:
2846:
2843:
2841:
2838:
2837:
2835:
2833:
2829:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2799:
2798:
2794:
2791:
2789:
2785:
2782:
2780:
2776:
2775:
2772:
2769:
2767:
2764:
2762:
2759:
2756:
2752:
2749:
2747:
2744:
2742:
2739:
2737:
2733:
2732:
2729:
2726:
2724:
2723:Prednimustine
2721:
2718:
2714:
2711:
2709:
2706:
2703:
2700:
2698:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2675:
2674:
2672:
2670:
2666:
2663:
2660:
2655:
2651:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2620:
2617:
2615:
2612:
2610:
2606:
2605:
2601:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2567:
2563:
2560:
2558:
2555:
2553:
2549:
2548:
2544:
2543:
2541:
2539:
2538:Intercalation
2535:
2531:
2524:
2521:
2519:
2515:
2514:
2510:
2509:
2507:
2505:
2501:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2440:
2439:
2435:
2434:
2432:
2430:
2426:
2423:
2420:
2415:
2411:
2400:
2396:
2395:
2391:
2390:
2388:
2386:
2382:
2375:
2372:
2370:
2366:
2365:
2361:
2360:
2356:
2352:
2351:
2347:
2346:
2342:
2341:+daunorubicin
2339:
2335:
2334:
2330:
2329:
2325:
2321:
2318:
2316:
2313:
2311:
2308:
2306:
2305:Doxifluridine
2303:
2301:
2298:
2296:
2292:
2291:
2287:
2286:
2284:
2282:
2278:
2271:
2268:
2266:
2262:
2261:
2257:
2255:
2254:Rabacfosadine
2252:
2250:
2247:
2244:
2241:
2239:
2236:
2234:
2230:
2229:
2225:
2221:
2220:
2216:
2212:
2211:
2207:
2206:
2204:
2202:
2198:
2191:
2188:
2186:
2182:
2181:
2177:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2155:
2154:
2150:
2149:
2147:
2145:
2141:
2138:
2135:
2130:
2124:
2121:
2117:
2113:
2102:
2098:
2097:
2093:
2090:
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2070:
2067:
2065:
2061:
2060:
2056:
2055:
2053:
2049:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2018:
2017:
2013:
2012:
2010:
2007:
2002:
1999:
1996:
1991:
1987:
1983:
1978:
1974:
1970:
1962:
1957:
1955:
1950:
1948:
1943:
1942:
1939:
1920:
1918:
1913:
1907:
1904:
1899:
1895:
1890:
1885:
1881:
1877:
1873:
1869:
1861:
1858:
1852:
1848:
1843:
1838:
1834:
1830:
1826:
1822:
1818:
1811:
1809:
1805:
1800:
1796:
1791:
1786:
1782:
1776:
1772:
1768:
1764:
1757:
1754:
1749:
1745:
1741:
1737:
1733:
1729:
1725:
1721:
1714:
1711:
1706:
1702:
1698:
1692:
1689:
1676:
1672:
1671:
1666:
1659:
1656:
1651:
1647:
1643:
1637:
1634:
1629:
1625:
1621:
1615:
1612:
1599:
1595:
1589:
1586:
1581:
1577:
1571:
1568:
1560:
1554:
1551:
1538:
1531:
1525:
1522:
1517:
1513:
1509:
1505:
1501:
1497:
1490:
1487:
1482:
1478:
1474:
1470:
1463:
1461:
1457:
1452:
1451:New Scientist
1448:
1441:
1438:
1433:
1429:
1424:
1419:
1415:
1411:
1407:
1403:
1399:
1392:
1390:
1388:
1384:
1379:
1375:
1371:
1364:
1362:
1360:
1356:
1351:
1347:
1343:
1339:
1335:
1331:
1327:
1323:
1316:
1313:
1308:
1304:
1297:
1294:
1281:
1279:
1274:
1268:
1266:
1264:
1262:
1258:
1245:
1241:
1235:
1233:
1231:
1227:
1214:
1210:
1204:
1201:
1188:
1184:
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1132:
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1088:hydrogenation
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1072:
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1060:
1056:
1048:
1046:
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1013:
1011:
1009:
1005:
1002:
994:
992:
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987:
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979:
971:
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948:
944:
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936:
932:
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922:
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912:
911:
905:
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890:
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848:
844:
840:
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823:
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779:
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765:
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760:
758:
755:
750:
743:
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737:
707:
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701:
696:
692:
688:
685:
683:
681:ECHA InfoCard
677:
669:
665:
664:DTXSID2046880
661:
660:
658:
649:
645:
638:
634:
633:
631:
629:
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614:
613:
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609:
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531:
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389:
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380:
376:
372:
369:
367:
363:
359:
357:
353:
349:
347:
343:
339:
335:
328:
326: Rx-only
319:
317:
307:
304:
294:
291:
281:
280:
278:
276:
272:
267:
259:
254:
251:
250:
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137:
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109:
105:
101:
100:
89:
45:
43:Pronunciation
41:
38:Clinical data
36:
32:
27:
19:
3726:Orphan drugs
3591:
3567:Tazemetostat
3531:Alitretinoin
3524:
3435:Estramustine
3415:Elsamitrucin
3405:Eflornithine
3359:Pegaspargase
3355:Asparaginase
3348:
3317:Testolactone
3310:
3298:
3286:
3240:
3225:Panobinostat
3208:
3178:
3166:
3154:
3142:
3113:
3078:
3066:
3019:
3015:Padeliporfin
2954:Dactinomycin
2950:Streptomyces
2931:Temozolomide
2926:Mitozolomide
2914:
2905:Mitobronitol
2894:Procarbazine
2887:
2875:Nonclassical
2800:
2777:
2771:Streptozocin
2736:Nitrosoureas
2734:
2708:Chlorambucil
2702:Trofosfamide
2688:Chlormethine
2683:Bendamustine
2676:
2614:Mitoxantrone
2609:Losoxantrone
2602:
2562:Daunorubicin
2545:
2511:
2448:Camptothecin
2436:
2392:
2362:
2348:
2331:
2315:Fluorouracil
2295:Capecitabine
2288:
2258:
2222:
2208:
2178:
2173:Pralatrexate
2163:Methotrexate
2151:
2094:
2057:
2014:
1925:30 September
1923:. Retrieved
1915:
1906:
1871:
1867:
1860:
1824:
1820:
1762:
1756:
1723:
1719:
1713:
1705:the original
1700:
1691:
1679:. Retrieved
1668:
1658:
1650:the original
1645:
1636:
1628:the original
1623:
1614:
1604:30 September
1602:. Retrieved
1600:. 8 May 2008
1597:
1588:
1580:the original
1570:
1553:
1541:. Retrieved
1536:
1524:
1499:
1495:
1489:
1472:
1468:
1450:
1440:
1405:
1401:
1378:the original
1373:
1325:
1321:
1315:
1306:
1302:
1296:
1286:30 September
1284:. Retrieved
1276:
1250:30 September
1248:. Retrieved
1243:
1219:30 September
1217:. Retrieved
1212:
1203:
1191:. Retrieved
1189:. 3 May 2021
1186:
1161:
1158:Legal status
1128:
1118:
1115:
1101:
1092:Ugi reaction
1052:
1042:
1033:
1030:
1025:
1014:Biosynthesis
998:
990:
975:
958:
955:
928:
920:
908:
894:
887:
878:
858:
855:
842:
838:
837:
826:
820:
637:ChEMBL297812
450:
446:
442:
438:
434:
430:
426:
422:
400:Mostly fecal
383:Elimination
275:Legal status
269:Legal status
158:License data
18:
3642:from market
3612:Vorasidenib
3592:Trabectedin
3577:Tiazofurine
3572:Tebentafusp
3557:Tagraxofusp
3515:Plitidepsin
3485:Mitoguazone
3425:Epacadostat
3395:Demecolcine
3339:Aflibercept
3312:Sex steroid
3185:Fuzuloparib
3126:Carfilzomib
3098:Palbociclib
3088:Abemaciclib
3041:Verteporfin
3005:Efaproxiral
2921:Dacarbazine
2883:Altretamine
2865:Satraplatin
2860:Oxaliplatin
2840:Carboplatin
2817:Triaziquone
2788:Mannosulfan
2766:Ranimustine
2746:Fotemustine
2587:Pirarubicin
2572:Doxorubicin
2566:+cytarabine
2552:Aclarubicin
2513:Podophyllum
2438:Camptotheca
2369:Azacitidine
2355:Gemcitabine
2310:Floxuridine
2243:Fludarabine
2238:Clofarabine
2224:Halogenated
2215:Pentostatin
2190:Raltitrexed
2158:Aminopterin
2101:Ixabepilone
2096:Epothilones
2064:Cabazitaxel
2041:Vinorelbine
2026:Vincristine
2021:Vinblastine
2006:microtubule
1874:(1): 1388.
1543:12 November
1328:(1): 1–27.
1303:Proceedings
1193:6 September
1078:diphosphine
961:dacarbazine
943:liposarcoma
904:E. J. Corey
865:orphan drug
839:Trabectedin
747: g·mol
687:100.223.368
617:CHEBI:84050
472:114899-77-3
405:Identifiers
238:Intravenous
194:Trabectedin
144:MedlinePlus
117:Other names
108:Trade names
23:Trabectedin
3695:Categories
3607:Verdinexor
3602:Venetoclax
3505:Oblimersen
3500:Navitoclax
3475:Lucanthone
3470:Lonidamine
3460:Lifileucel
3455:Ivosidenib
3450:Imetelstat
3420:Enasidenib
3410:Elesclomol
3375:Bexarotene
3370:Belzutifan
3305:Bexarotene
3293:Atrasentan
3268:Umbralisib
3263:Idelalisib
3253:Copanlisib
3235:Vorinostat
3230:Romidepsin
3220:Entinostat
3215:Belinostat
3173:Masoprocol
3161:Tiazofurin
3149:Anagrelide
3121:Bortezomib
3108:Seliciclib
3103:Ribociclib
3083:inhibitors
3073:Tipifarnib
3036:Temoporfin
3031:Talaporfin
2969:Plicamycin
2964:Mitomycins
2910:Pipobroman
2889:Hydrazines
2855:Nedaplatin
2807:Carboquone
2802:Aziridines
2793:Treosulfan
2741:Carmustine
2728:Uramustine
2697:Ifosfamide
2669:Alkylating
2630:Bisantrene
2619:Pixantrone
2592:Valrubicin
2582:Idarubicin
2577:Epirubicin
2523:Teniposide
2478:Lurtotecan
2473:Irinotecan
2374:Decitabine
2338:Cytarabine
2281:Pyrimidine
2270:Tioguanine
2260:Thiopurine
2249:Nelarabine
2233:Cladribine
2185:Pemetrexed
2168:Pemetrexed
2144:Folic acid
2084:Paclitaxel
2036:Vinflunine
1912:"Yondelis"
1183:"Yondelis"
1166:References
1131:ETH Zürich
1031:Candidatus
935:ifosfamide
895:Candidatus
885:sea squirt
752:3D model (
740:Molar mass
577:ID0YZQ2TCP
548:ChemSpider
508:IUPHAR/BPS
463:CAS Number
414:IUPAC name
377:-mediated)
366:Metabolism
3652:Phase III
3640:Withdrawn
3617:Vosaroxin
3597:Veliparib
3552:Sotorasib
3542:Selinexor
3536:Tretinoin
3526:Retinoids
3440:Glasdegib
3385:Celecoxib
3334:Adagrasib
3258:Duvelisib
3248:Alpelisib
3203:Rucaparib
3190:Niraparib
3131:Oprozomib
3093:Alvocidib
2959:Bleomycin
2916:Triazenes
2900:Etoglucid
2845:Cisplatin
2761:Nimustine
2755:Semustine
2751:Lomustine
2713:Melphalan
2640:Menogaril
2635:Crisnatol
2625:Amsacrine
2597:Zorubicin
2557:Amrubicin
2518:Etoposide
2493:Topotecan
2488:Silatecan
2483:Rubitecan
2468:Gimatecan
2453:Cositecan
2443:Belotecan
2119:inhibitor
2089:Tesetaxel
2079:Ortataxel
2074:Larotaxel
2069:Docetaxel
2031:Vindesine
1821:Neoplasia
1701:PharmaMar
1082:catalyzed
995:Structure
899:PharmaMar
396:Excretion
385:half-life
360:94 to 98%
231:Routes of
205:Pregnancy
136:Monograph
130:Drugs.com
3685:Medicine
3490:Mitotane
3430:Eribulin
3198:Olaparib
3136:Ixazomib
2812:Thiotepa
2784:Busulfan
2463:Exatecan
2300:Carmofur
2008:assembly
1971: /
1898:38360910
1851:21403840
1799:32586501
1740:20647340
1675:Archived
1516:10956543
1432:21875091
1350:25117225
1342:10608919
1244:DailyMed
1119:in vitro
1107:FUS-CHOP
1008:cysteine
1004:moieties
843:Yondelis
829:(verify)
528:DrugBank
373:(mostly
245:ATC code
207:category
189:DailyMed
112:Yondelis
3731:Phenols
2419:S phase
2320:Tegafur
2134:S phase
2059:Taxanes
1995:M phase
1842:3033593
1790:6169485
1748:6723817
1598:Reuters
1423:3220770
1076:-based
1074:rhodium
963:), the
704:Formula
537:DB05109
483:PubChem
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150:a615059
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3671:Portal
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2201:Purine
2004:Block
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1340:
1071:chiral
1069:, and
1065:, the
965:US FDA
778:SMILES
745:761.84
628:ChEMBL
597:D06199
497:108150
375:CYP3A4
316:℞-only
314:
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288:
187:
177:by INN
170:
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3156:IMPDI
3051:Other
1919:(EMA)
1744:S2CID
1681:7 May
1562:(PDF)
1533:(PDF)
1346:S2CID
1280:(EMA)
1213:(emc)
1135:UNIST
798:InChI
754:JSmol
608:ChEBI
557:97236
371:Liver
3242:PIKI
3210:HDAC
2659:CCNS
1927:2020
1894:PMID
1847:PMID
1795:PMID
1775:ISBN
1736:PMID
1683:2011
1606:2020
1545:2019
1512:PMID
1428:PMID
1338:PMID
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1986:SPs
1977:L01
1884:hdl
1876:doi
1837:PMC
1829:doi
1785:PMC
1767:doi
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1477:doi
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1330:doi
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