550:
100% mycological cure over a long-term period (28–34 days). This study focused on the drug as an 80 mg vaginal suppository, taken three times overnight by 10 women. In another placebo-controlled, double blind study by
Schmidt et al., the efficacy of different concentrations of terconazole creams were tested. Cream was applied for three days to 24 women between the ages of 18 and 60. The results showed 0.8% terconazole mycologic cure rates were 83.3% within 1–3 days of starting treatment, 83.3% within 8–11 days of treatment and 58.3% within 30–35 days of treatment. The suppository is more effective after a long-term follow-up than terconazole as a cream or other intravaginal treatments.
748:, was available on the market, replacing rare and expensive treatments. It was effective in its function but was very toxic and only used for serious infections. The drug was infused into the bloodstream and could cause kidney damage and other side effects. The first azole compounds to replace this treatment were synthesized in the late 1960s and early 1970s and administered to humans under strict care. These compounds were imidazoles, a molecule containing two non-adjacent nitrogen atoms in a 5 membered ring. The first oral antimycotic imidazole, called
373:
350:
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similar results in pregnant vulvovaginal candidiasis, non-pregnant vulvovaginal candidiasis and healthy women. The half-life of terconazole in blood is recorded to be around 6.9 hours over a range of 4–11.3 hours). Radioactivity of plasma terconazole is low compared to terconazole at 0.6%. Excretion of radioactivity is via two routes, renal (32–53%) and fecal (47–52%). Metabolism is extensive and is highly protein bound (94.9%) with the degree of binding being independent of drug concentration.
621:
42:
716:: a major constituent in the ergosterol biosynthesis pathway for the creation of cell membrane constituents in yeast. This structure provides the membrane with fluidity. This occurs by transforming lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-β-ol. This stops respiration by prohibiting reduction of
534:. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell. It has a relatively broad spectrum compared to azole compounds but not triazole compounds. Testing shows that it is a suitable compound for prophylaxis for those that suffer from chronic vulvovaginal candidiasis.
585:
Terconazole is not considered hazardous when handled under normal conditions. It is generally non-flammable and non-carcinogenic. Generally is non-toxic, however, can emit toxic fumes when dust is set alight. Can cause respiratory distress as dust. Can be absorbed by embryo within the first trimester
720:
to NAD. This stops biosynthesis of cell membrane products as well as transport and catabolism. Eventually, membrane fluidity and activity of membrane bound enzymes become depleted. It has also been shown to inhibit morphologic change of yeast as well as cell adherence and is directly toxic to yeast.
549:
A review found that short-term rates for intravaginally administered azole treatments shows cure in 80% of cases in a short term follow-up and 66% over long term follow-up. In a double-blind study by Slavin in 1992, terconazole showed a 75% mycological cure over a short-term period (7–14 days) and
735:
Absorption of terconazole is 5–8% in patients that have had a hysterectomy and 12–16% in other patients. In those that administered 0.8% terconazole, plasma concentrations of the drug remained quite low with the peak plasma concentration being 0.006 mcg at 6.6 hours. Those metabolism rates show
752:, was available on the market in 1981. Triazole based drugs came shortly after and quickly gained popularity due to its broader spectrum of antifungal activity and less toxicity. Terconazole was the first triazole-based antifungal drug synthesized for human use.
712:. The gene ERG11 controls lanosterol creation. Lanosterol is found within the yeast plasma membrane. It is a class of methylsterol. Within a normal yeast cell, lanosterol is demethylated using 14α-demethylation. This process creates
1316:
Isaacson DM, Tolman EL, Tobia AJ, Rosenthale ME, McGuire JL, Vanden
Bossche H, et al. (March 1988). "Selective inhibition of 14 alpha-desmethyl sterol synthesis in Candida albicans by terconazole, a new triazole antimycotic".
1599:
2811:
448:
672:-1,2,4-triazole. Terconazole has a melting point of 126.3 °C (259.34 °F). The molecular weight of terconazole is 532.462 g/mol. Terconazole is synthesized using two chemical compounds:
1592:
949:
Slavin MB, Benrubi GI, Parker R, Griffin CR, Magee MJ (October 1992). "Single dose oral fluconazole vs intravaginal terconazole in treatment of
Candida vaginitis. Comparison and pilot study".
490:
InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1
692:. Terconazole is non-reactive except when exposed to strong oxidizing agents or strong bases due to the nitrogen attached to the triazole ring. It has been found to be photosensitive.
542:
Terconazole is approved to treat vulvovaginal candidiasis (vaginal thrush). It works as a broad spectrum antifungal and has shown to be an effective first-line treatment against other
760:
species. Since creation, terconazole has been superseded by second-generation triazoles due to their even broader spectrum and higher activity levels against resistant pathogens like
1585:
1042:. Office of Surveillance, Epidemiology, and Laboratory Services, Centers for Disease Control and Prevention (CDC), U.S. Department of Health and Human Services, Atlanta, GA 30333
96:
617:
Terconazole synthesis synologous with ketoconazole except for the fact that triazole and not imidazole heterocyclic ring is used, and that isopropyl group instead of acetamide.
2804:
582:
and allergic reactions. Flu-like symptoms have been recorded in those that take suppositories greater than 160 mg. May cause birth defects if used in the first trimester.
506:
3825:
2797:
64:
462:
1509:
Heeres J, Hendrickx R, Van Cutsem J (April 1983). "Antimycotic azoles. 6. Synthesis and antifungal properties of terconazole, a novel triazole ketal".
1161:
Heeres J, Hendrickx R, Van Cutsem J (April 1983). "Antimycotic azoles. 6. Synthesis and antifungal properties of terconazole, a novel triazole ketal".
640:
1106:
1061:
Faro S, Apuzzio J, Bohannon N, Elliott K, Martens MG, Mou SM, et al. (March 1997). "Treatment
Considerations in Vulvovaginal Candidiasis".
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1553:
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Terconazole targets fungi specifically since humans do not use lanosterol in this pathway. This process does not affect all fungi such as
979:
Schmitt C, Sobel J, Meriwether C (September 1990). "Comparison of 0.8% and 1.6% terconazole cream in severe vulvovaginal candidiasis".
3855:
1145:
717:
482:
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1138:
Kucers' the Use of
Antibiotics Sixth Edition: a Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs
147:
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2522:
902:"Oral versus intra-vaginal imidazole and triazole anti-fungal treatment of uncomplicated vulvovaginal candidiasis (thrush)"
3840:
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at 1300 °C (2372 °F) to give many different types of triazole derivatives. These are purified using alcohol and
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developed it in 1983. Previously, all triazole based drugs targeted fungal infections related to plants from
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Grayson ML, Crowe SM, McCarthy JS, Mills J, Mouton JW, Norrby SR, Paterson DL, Pfaller MA, eds. (2010).
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753:
3123:
3113:
1199:
Cauwenbergh G, Vanden
Bossche H (August 1989). "Terconazole. Pharmacology of a new antimycotic agent".
318:
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1006:
Maibach HI, Farage MA, eds. (2006). "Vulvar
Therapies: Evidence vs. Testimony. Fungal: Candidiasis.".
636:
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3118:
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900:
Denison HJ, Worswick J, Bond CM, Grimshaw JM, Mayhew A, Gnani
Ramadoss S, et al. (August 2020).
800:
Tolman EL, Isaacson DM, Rosenthale ME, McGuire JL, Van Cutsem J, Borgers M, et al. (June 1986).
3820:
3457:
3263:
3163:
3087:
2517:
2333:
1905:
772:
Terconazole is a white, odourless powder. It can be purchased commercially in the following forms:
345:
164:
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851:"Terconazole cream for non-Candida albicans fungal vaginitis: results of a retrospective analysis"
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of pregnancy and cause birth defects. Cross inhibition shows that there may be some toxicity.
54:
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598:. A precipitate is formed upon combination of both drugs. Terconazole may weaken latex-based
298:
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1989:
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1641:
1275:
Yoshida Y (1988). "Cytochrome P450 of Fungi: Primary Target for Azole
Antifungal Agents".
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1140:(6th ed.). Boca Raton, FL: CRC Press. Taylor & Francis Group. pp. 1933–5.
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570:, burning or discomfort. Other side effects may include abdominal pain or cramps,
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1033:"Sexually Transmitted Diseases Treatment Guidelines, 2010. Vol. 59. No. RR-12"
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713:
705:
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species. It also shows effectiveness against dermatomycoses in animal models.
527:
424:
229:
1032:
668:. The chemical name for terconazole is 1-{methyl}-1,3-dioxolan-2-yl]methyl}-1
3666:
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2017:
1979:
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1084:(2nd ed.). Burlington, MA: Jones & Bartlett Learning. p. 312.
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1010:(1st ed.). New York: Informa Healthcare USA, Inc. pp. 128–129.
817:
677:
559:
209:
1522:
1436:
1243:
1174:
779:
Terconazole 0.8% cream 5 g applied intravaginally once a day for 3 days;
776:
Terconazole 0.4% cream 5 g applied intravaginally once a day for 7 days;
218:
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1969:
1681:
764:
It is still used as a treatment in cases of resistance to other drugs.
184:
17:
802:"Anticandidal activities of terconazole, a broad-spectrum antimycotic"
782:
Terconazole 80 mg vaginal suppository used once daily for 3 days.
709:
676:- methyl benzoate and the sodium salt of triazole, created by mixing
599:
575:
309:
1548:(3rd ed.). St. Louis, Missouri: Elsevier. pp. 1558–1559.
278:
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619:
611:
579:
447:
438:
289:
567:
563:
269:
2793:
2021:
1581:
1573:
Information about terconazole from the United States
Government
1228:"Overview of medically important antifungal azole derivatives"
470:
Clc1ccc(c(Cl)c1)4(O(COc3ccc(N2CCN(C(C)C)CC2)cc3)CO4)Cn5ncnc5
334:
1544:
Mosby (2012). "Terconazole". In White K, Watrous J (eds.).
1082:
Frequently Prescribed Medications: Drugs You Need to Know
2832:
614:
with broad-spectrum antifungal/antimycotic tendencies.
513:
744:
In 1940, the first commercial antifungal drug, called
1419:
Sheehan DJ, Hitchcock CA, Sibley CM (January 1999).
700:
Terconazole binds to the heme iron component on the
558:
The most common side effects of terconazole include
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684:. These are put in a solution and catalyzed using
1470:"History of the development of azole derivatives"
849:Sood G, Nyirjesy P, Weitz MV, Chatwani A (2000).
855:Infectious Diseases in Obstetrics and Gynecology
197:
172:
1421:"Current and emerging azole antifungal agents"
1194:
1192:
1113:. State Government of Victoria. Archived from
1040:USA Centers for Disease Control and Prevention
951:The Journal of the Florida Medical Association
2805:
2033:
1593:
1546:Mosby's Drug Reference for Health Professions
594:Terconazole may interact with the spermicide
8:
1031:Workowski KA, Berman S (December 17, 2010).
1008:The Vulva: Anatomy, Physiology and Pathology
32:
3088:
906:The Cochrane Database of Systematic Reviews
3139:Allopregnanedione (5α-dihydroprogesterone)
2812:
2798:
2790:
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2381:
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2081:
2070:
2040:
2026:
2018:
1795:
1600:
1586:
1578:
371:
348:
237:
155:1-methoxy]phenyl]-4-propan-2-yl-piperazine
1485:
1444:
1395:
1359:. Stanford University, Stanford, CA 94305
1319:The Journal of Antimicrobial Chemotherapy
1251:
974:
972:
925:
876:
866:
825:
257:
2837:Tooltip Constitutive androstane receptor
1384:Infectious Diseases in Clinical Practice
792:
487:
467:
344:
217:
152:
87:
3592:Pregnanedione (5β-dihydroprogesterone)
2978:Pregnanedione (5β-dihydroprogesterone)
648:Terconazole has the chemical formula C
362:
31:
3826:Lanosterol 14α-demethylase inhibitors
806:Antimicrobial Agents and Chemotherapy
317:
297:
73:
7:
1201:The Journal of Reproductive Medicine
108:
1474:Clinical Microbiology and Infection
1353:"C-4 Methylsterol Oxidase Activity"
277:
188:
1277:Current Topics in Medical Mycology
25:
1279:. Vol. 2. pp. 388–418.
1080:Mancano MA, Gallagher JC (2013).
1487:10.1111/j.1470-9465.2004.00841.x
1397:10.1097/00019048-199409000-00002
1380:"Mini Review. Candida Vaginitis"
1105:Melbourne Sexual Health Centre.
408:
402:
396:
40:
2523:thymidylate synthase inhibitors
495:Key:BLSQLHNBWJLIBQ-OZXSUGGESA-N
3144:Allopregnanolone (brexanolone)
1511:Journal of Medicinal Chemistry
1163:Journal of Medicinal Chemistry
918:10.1002/14651858.CD002845.pub3
414:
390:
1:
3799:Receptor/signaling modulators
3757:Tropanyl 3,5-dimethulbenzoate
3607:Pregnenolone 16α-carbonitrile
1425:Clinical Microbiology Reviews
1357:Saccharomyces Genome Database
1232:Clinical Microbiology Reviews
562:, vulvar/vaginal irritation,
1285:10.1007/978-1-4612-3730-3_11
3334:Dodecylbenzenesulfonic acid
3093:Tooltip Pregnane X receptor
2821:Xenobiotic-sensing receptor
1226:Fromtling RA (April 1988).
3872:
1468:Maertens JA (March 2004).
727:, which lacks lanosterol.
610:Terconazole is a triazole
380:Chemical and physical data
3856:Phenylethanolamine ethers
3790:
2750:
2591:bromochlorosalicylanilide
2561:Aminoacyl tRNA synthetase
981:Obstetrics and Gynecology
868:10.1155/S1064744900000351
503:
478:
458:
143:
39:
3717:Testosterone isocaproate
3632:Reverse triiodothyronine
708:of fungi, also known as
3109:17α-Hydroxyprogesterone
3104:17α-Hydroxypregnenolone
2001:Lactobacillus fermentum
624:Terconazole synthesis:
532:vaginal yeast infection
2375:Squalene monooxygenase
2212:Systemic: ketoconazole
1710:Diiodohydroxyquinoline
724:Pneumocystis jirovecii
645:
2848:6,7-Dimethylesculetin
2403:Systemic: terbinafine
1111:Better Health Channer
754:Janssen Pharmaceutica
632:U.S. patent 4,223,036
627:U.S. patent 4,144,346
623:
3841:Triazole antifungals
3435:Hypericum perforatum
3424:Hetacillin potassium
2691:Whitfield's ointment
2518:Pyrimidine analogues
2334:Polyene antimycotics
1331:10.1093/jac/21.3.333
1207:(8 Suppl): 588–592.
818:10.1128/aac.29.6.986
3846:Isopropyl compounds
3264:Cyproterone acetate
3164:Amlodipine besylate
1523:10.1021/jm00358a032
1437:10.1128/cmr.12.1.40
1244:10.1128/CMR.1.2.187
1175:10.1021/jm00358a032
987:(3 Pt 1): 414–416.
696:Mechanism of action
530:drug used to treat
36:
3737:Thonzonium bromide
3492:Methylprednisolone
3293:prasterone sulfate
2777:Never to phase III
2681:tribromometacresol
2651:sodium thiosulfate
2646:selenium disulfide
2542:Mitotic inhibitors
1063:The Female Patient
646:
3808:
3807:
3442:Indinavir sulfate
3149:Alpha-Lipoic acid
3124:Δ-Androstenedione
3114:Δ-Androstenedione
2787:
2786:
2579:
2578:
2505:
2504:
2456:β-glucan synthase
2450:
2449:
2429:
2428:
2328:
2327:
2015:
2014:
1953:
1952:
1555:978-0-323-09574-7
1480:(Suppl 1): 1–10.
1378:Sobel JD (1994).
1294:978-1-4612-8323-2
1117:on 5 October 2015
1091:978-1-4496-9884-3
1017:978-0-8493-3608-9
521:
520:
449:Interactive image
330:CompTox Dashboard
27:Chemical compound
16:(Redirected from
3863:
3727:Thiamylal sodium
3462:γ-linolenic acid
3458:α-Linolenic acid
3456:Linolenic acid:
3447:Lasalocid sodium
3437:(St John's wort)
3329:Docusate calcium
3259:Cyclophosphamide
3134:Allopregnanediol
3119:Δ-Androstenediol
3094:
3090:
3048:Ethinylestradiol
2898:Cyclophosphamide
2838:
2834:
2814:
2807:
2800:
2791:
2686:undecylenic acid
2636:potassium iodide
2514:
2382:
2098:
2082:
2071:
2042:
2035:
2028:
2019:
1945:Methylrosaniline
1796:
1602:
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1122:
1107:"Vaginal thrush"
1102:
1096:
1095:
1077:
1071:
1070:
1058:
1052:
1051:
1049:
1047:
1037:
1028:
1022:
1021:
1003:
997:
996:
976:
967:
966:
946:
940:
939:
929:
897:
891:
890:
880:
870:
861:(5–6): 240–243.
846:
840:
839:
829:
797:
762:Aspergillus spp.
686:dimethyl sulfate
644:
643:
639:
634:
629:
517:
516:
509:
451:
431:
416:
410:
404:
398:
392:
375:
364:
353:
352:
338:
336:
321:
301:
281:
261:
241:
221:
201:
191:
190:
176:
112:
91:
77:
44:
37:
35:
21:
3871:
3870:
3866:
3865:
3864:
3862:
3861:
3860:
3811:
3810:
3809:
3804:
3786:
3687:Suberoylanilide
3404:Fluorometholone
3299:Dibunate sodium
3179:Aurothioglucose
3092:
3082:
3018:3,17β-Estradiol
2836:
2826:
2818:
2788:
2783:
2782:
2767:Clinical trials
2746:
2575:
2555:
2536:
2521:
2501:
2458:
2446:
2425:
2406:
2402:
2377:
2369:
2361:
2336:
2324:
2305:
2258:fosravuconazole
2215:
2091:
2090:lanosterol 14α-
2077:
2066:
2060:
2046:
2016:
2011:
1990:Povidone-iodine
1949:
1928:
1900:
1882:
1785:
1767:
1739:
1695:
1676:
1652:Oxytetracycline
1642:Chloramphenicol
1623:
1612:anti-infectives
1606:
1569:
1564:
1563:
1556:
1543:
1542:
1538:
1508:
1507:
1503:
1467:
1466:
1462:
1418:
1417:
1413:
1377:
1376:
1372:
1362:
1360:
1351:
1350:
1346:
1315:
1314:
1310:
1295:
1274:
1273:
1269:
1225:
1224:
1220:
1198:
1197:
1190:
1160:
1159:
1155:
1148:
1135:
1134:
1130:
1120:
1118:
1104:
1103:
1099:
1092:
1079:
1078:
1074:
1060:
1059:
1055:
1045:
1043:
1035:
1030:
1029:
1025:
1018:
1005:
1004:
1000:
978:
977:
970:
957:(10): 693–696.
948:
947:
943:
912:(8): CD002845.
899:
898:
894:
848:
847:
843:
799:
798:
794:
789:
770:
768:Available forms
742:
733:
702:cytochrome P450
698:
667:
663:
659:
655:
651:
641:
635:
630:
625:
608:
592:
556:
540:
512:
510:
507:(what is this?)
504:
499:
496:
491:
486:
485:
474:
471:
466:
465:
454:
429:
419:
413:
407:
401:
395:
356:
332:
324:
304:
284:
264:
244:
224:
204:
187:
179:
159:
156:
151:
150:
130:Protein binding
122:Pharmacokinetic
116:
28:
23:
22:
15:
12:
11:
5:
3869:
3867:
3859:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3813:
3812:
3806:
3805:
3803:
3802:
3795:
3791:
3788:
3787:
3785:
3784:
3779:
3770:
3769:
3764:
3759:
3754:
3752:Troleandomycin
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3714:
3709:
3704:
3699:
3694:
3689:
3684:
3679:
3674:
3672:Spironolactone
3669:
3664:
3659:
3654:
3649:
3644:
3639:
3634:
3629:
3624:
3619:
3614:
3609:
3604:
3599:
3594:
3589:
3584:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3542:Norelgestromin
3539:
3534:
3529:
3524:
3519:
3514:
3509:
3504:
3499:
3494:
3489:
3484:
3479:
3474:
3469:
3464:
3454:
3449:
3444:
3439:
3431:
3426:
3421:
3416:
3411:
3406:
3401:
3399:Flucloxacillin
3396:
3391:
3386:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3346:
3341:
3336:
3331:
3326:
3321:
3316:
3311:
3306:
3301:
3296:
3286:
3276:
3271:
3266:
3261:
3256:
3254:Corticosterone
3251:
3246:
3241:
3236:
3231:
3226:
3221:
3219:Chlorpromazine
3216:
3211:
3206:
3201:
3196:
3191:
3186:
3181:
3176:
3171:
3166:
3161:
3156:
3151:
3146:
3141:
3136:
3131:
3126:
3121:
3116:
3111:
3106:
3097:
3095:
3084:
3083:
3081:
3080:
3075:
3070:
3065:
3060:
3055:
3050:
3045:
3040:
3038:17-Androstanol
3035:
3033:3β-Androstanol
3030:
3028:3α-Androstenol
3025:
3023:3α-Androstanol
3020:
3011:
3010:
3005:
3000:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2925:
2920:
2915:
2905:
2900:
2895:
2890:
2885:
2880:
2878:Chlorpromazine
2875:
2870:
2865:
2860:
2855:
2850:
2841:
2839:
2828:
2827:
2819:
2817:
2816:
2809:
2802:
2794:
2785:
2784:
2781:
2780:
2779:
2778:
2775:
2764:
2758:
2752:
2751:
2748:
2747:
2745:
2744:
2739:
2734:
2725:
2720:
2715:
2710:
2705:
2700:
2698:citronella oil
2694:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2653:
2648:
2643:
2641:salicylic acid
2638:
2633:
2628:
2623:
2618:
2613:
2611:crystal violet
2608:
2603:
2598:
2596:chlorophetanol
2593:
2587:
2585:
2581:
2580:
2577:
2576:
2574:
2573:
2566:
2564:
2557:
2556:
2554:
2553:
2546:
2544:
2538:
2537:
2535:
2534:
2527:
2525:
2511:
2507:
2506:
2503:
2502:
2500:
2499:
2494:
2488:
2483:
2478:
2473:
2462:
2460:
2452:
2451:
2448:
2447:
2445:
2444:
2437:
2435:
2431:
2430:
2427:
2426:
2424:
2423:
2416:
2414:
2408:
2407:
2405:
2404:
2397:
2390:
2388:
2379:
2371:
2370:
2368:
2367:
2364:amphotericin B
2356:
2351:
2344:
2342:
2330:
2329:
2326:
2325:
2323:
2322:
2315:
2313:
2307:
2306:
2304:
2303:
2298:
2291:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2253:fosfluconazole
2250:
2243:
2242:
2237:
2232:
2225:
2223:
2217:
2216:
2214:
2213:
2209:
2208:
2203:
2198:
2193:
2188:
2183:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2143:
2138:
2133:
2128:
2123:
2118:
2113:
2106:
2104:
2095:
2079:
2068:
2062:
2061:
2047:
2045:
2044:
2037:
2030:
2022:
2013:
2012:
2010:
2009:
2004:
1997:
1992:
1987:
1982:
1977:
1972:
1967:
1961:
1959:
1955:
1954:
1951:
1950:
1948:
1947:
1942:
1936:
1934:
1930:
1929:
1927:
1926:
1924:Amphotericin B
1921:
1916:
1910:
1908:
1902:
1901:
1899:
1898:
1892:
1890:
1884:
1883:
1881:
1880:
1875:
1870:
1865:
1860:
1855:
1850:
1845:
1840:
1835:
1830:
1825:
1820:
1815:
1810:
1804:
1802:
1793:
1787:
1786:
1784:
1783:
1777:
1775:
1769:
1768:
1766:
1765:
1760:
1755:
1749:
1747:
1741:
1740:
1738:
1737:
1732:
1730:Broxyquinoline
1727:
1722:
1720:Chlorquinaldol
1717:
1712:
1706:
1704:
1697:
1696:
1694:
1693:
1687:
1685:
1678:
1677:
1675:
1674:
1669:
1664:
1659:
1654:
1649:
1644:
1639:
1633:
1631:
1625:
1624:
1607:
1605:
1604:
1597:
1590:
1582:
1576:
1575:
1568:
1567:External links
1565:
1562:
1561:
1554:
1536:
1517:(4): 611–613.
1501:
1460:
1411:
1390:(5): 334–339.
1370:
1344:
1325:(3): 333–343.
1308:
1293:
1267:
1238:(2): 187–217.
1218:
1188:
1169:(4): 611–613.
1153:
1147:978-0340927670
1146:
1128:
1097:
1090:
1072:
1053:
1023:
1016:
998:
968:
941:
892:
841:
812:(6): 986–991.
791:
790:
788:
785:
784:
783:
780:
777:
769:
766:
746:amphotericin B
741:
738:
732:
729:
697:
694:
690:chromatography
682:sodium hydride
665:
661:
657:
653:
649:
607:
604:
591:
588:
555:
552:
539:
536:
519:
518:
501:
500:
498:
497:
494:
492:
489:
481:
480:
479:
476:
475:
473:
472:
469:
461:
460:
459:
456:
455:
453:
452:
444:
442:
434:
433:
427:
421:
420:
417:
411:
405:
399:
393:
388:
382:
381:
377:
376:
366:
358:
357:
355:
354:
341:
339:
326:
325:
323:
322:
314:
312:
306:
305:
303:
302:
294:
292:
286:
285:
283:
282:
274:
272:
266:
265:
263:
262:
254:
252:
246:
245:
243:
242:
234:
232:
226:
225:
223:
222:
214:
212:
206:
205:
203:
202:
194:
192:
181:
180:
178:
177:
169:
167:
161:
160:
158:
157:
154:
146:
145:
144:
141:
140:
136:
135:
132:
126:
125:
118:
117:
115:
114:
101:
99:
93:
92:
85:
79:
78:
71:
61:
60:
57:
51:
50:
46:
45:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3868:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3831:Phenol ethers
3829:
3827:
3824:
3822:
3819:
3818:
3816:
3801:
3800:
3796:
3793:
3792:
3789:
3783:
3780:
3778:
3775:
3772:
3771:
3768:
3765:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3698:
3695:
3693:
3692:Sulfisoxazole
3690:
3688:
3685:
3683:
3680:
3678:
3675:
3673:
3670:
3668:
3665:
3663:
3660:
3658:
3655:
3653:
3650:
3648:
3645:
3643:
3640:
3638:
3635:
3633:
3630:
3628:
3625:
3623:
3620:
3618:
3615:
3613:
3610:
3608:
3605:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3568:
3567:Phenobarbital
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3545:
3543:
3540:
3538:
3535:
3533:
3530:
3528:
3525:
3523:
3520:
3518:
3515:
3513:
3510:
3508:
3505:
3503:
3500:
3498:
3495:
3493:
3490:
3488:
3485:
3483:
3480:
3478:
3475:
3473:
3470:
3468:
3465:
3463:
3459:
3455:
3453:
3452:Levothyroxine
3450:
3448:
3445:
3443:
3440:
3438:
3436:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3414:Guggulsterone
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3309:Dicloxacillin
3307:
3305:
3302:
3300:
3297:
3294:
3290:
3287:
3284:
3280:
3277:
3275:
3274:Dexamethasone
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3217:
3215:
3212:
3210:
3209:Cephaloridine
3207:
3205:
3202:
3200:
3197:
3195:
3192:
3190:
3187:
3185:
3182:
3180:
3177:
3175:
3172:
3170:
3167:
3165:
3162:
3160:
3157:
3155:
3152:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3099:
3098:
3096:
3091:
3085:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3013:
3012:
3009:
3008:Valproic acid
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2968:Phenobarbital
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2913:
2909:
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2868:Carbamazepine
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2843:
2842:
2840:
2835:
2829:
2825:
2822:
2815:
2810:
2808:
2803:
2801:
2796:
2795:
2792:
2776:
2774:
2771:
2770:
2768:
2765:
2762:
2759:
2757:
2754:
2753:
2749:
2743:
2740:
2738:
2735:
2733:
2729:
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2704:
2701:
2699:
2696:
2695:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2639:
2637:
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2602:
2601:chlorphenesin
2599:
2597:
2594:
2592:
2589:
2588:
2586:
2582:
2572:
2568:
2567:
2565:
2562:
2558:
2552:
2548:
2547:
2545:
2543:
2539:
2533:
2529:
2528:
2526:
2524:
2519:
2515:
2512:
2510:Intracellular
2508:
2498:
2497:ibrexafungerp
2495:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2471:anidulafungin
2468:
2467:echinocandins
2464:
2463:
2461:
2457:
2453:
2443:
2439:
2438:
2436:
2432:
2422:
2418:
2417:
2415:
2413:
2409:
2401:
2398:
2396:
2392:
2391:
2389:
2387:
2383:
2380:
2376:
2372:
2365:
2360:
2357:
2355:
2352:
2350:
2346:
2345:
2343:
2340:
2335:
2331:
2321:
2317:
2316:
2314:
2312:
2308:
2302:
2299:
2297:
2293:
2292:
2289:
2286:
2284:
2281:
2279:
2278:oteseconazole
2276:
2274:
2271:
2269:
2268:isavuconazole
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2245:
2244:
2241:
2238:
2236:
2233:
2231:
2230:efinaconazole
2227:
2226:
2224:
2222:
2218:
2211:
2210:
2207:
2204:
2202:
2199:
2197:
2196:sertaconazole
2194:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2151:fenticonazole
2149:
2147:
2144:
2142:
2139:
2137:
2134:
2132:
2129:
2127:
2124:
2122:
2121:chlormidazole
2119:
2117:
2114:
2112:
2108:
2107:
2105:
2103:
2099:
2096:
2093:
2087:
2083:
2080:
2076:
2072:
2069:
2063:
2058:
2054:
2050:
2043:
2038:
2036:
2031:
2029:
2024:
2023:
2020:
2008:
2007:Copper usnate
2005:
2003:
2002:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1963:
1962:
1960:
1956:
1946:
1943:
1941:
1938:
1937:
1935:
1931:
1925:
1922:
1920:
1917:
1915:
1912:
1911:
1909:
1907:
1903:
1897:
1894:
1893:
1891:
1889:
1885:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1859:
1858:Propenidazole
1856:
1854:
1851:
1849:
1848:Fenticonazole
1846:
1844:
1841:
1839:
1836:
1834:
1831:
1829:
1826:
1824:
1821:
1819:
1816:
1814:
1811:
1809:
1808:Metronidazole
1806:
1805:
1803:
1801:
1797:
1794:
1792:
1788:
1782:
1781:Sulfatolamide
1779:
1778:
1776:
1774:
1770:
1764:
1763:Ascorbic acid
1761:
1759:
1756:
1754:
1751:
1750:
1748:
1746:
1745:Organic acids
1742:
1736:
1733:
1731:
1728:
1726:
1723:
1721:
1718:
1716:
1713:
1711:
1708:
1707:
1705:
1702:
1698:
1692:
1689:
1688:
1686:
1683:
1679:
1673:
1670:
1668:
1665:
1663:
1660:
1658:
1655:
1653:
1650:
1648:
1645:
1643:
1640:
1638:
1635:
1634:
1632:
1630:
1626:
1621:
1617:
1613:
1610:
1609:Gynecological
1603:
1598:
1596:
1591:
1589:
1584:
1583:
1580:
1574:
1571:
1570:
1566:
1557:
1551:
1547:
1540:
1537:
1532:
1528:
1524:
1520:
1516:
1512:
1505:
1502:
1497:
1493:
1488:
1483:
1479:
1475:
1471:
1464:
1461:
1456:
1452:
1447:
1442:
1438:
1434:
1430:
1426:
1422:
1415:
1412:
1407:
1403:
1398:
1393:
1389:
1385:
1381:
1374:
1371:
1358:
1354:
1348:
1345:
1340:
1336:
1332:
1328:
1324:
1320:
1312:
1309:
1304:
1300:
1296:
1290:
1286:
1282:
1278:
1271:
1268:
1263:
1259:
1254:
1249:
1245:
1241:
1237:
1233:
1229:
1222:
1219:
1214:
1210:
1206:
1202:
1195:
1193:
1189:
1184:
1180:
1176:
1172:
1168:
1164:
1157:
1154:
1149:
1143:
1139:
1132:
1129:
1116:
1112:
1108:
1101:
1098:
1093:
1087:
1083:
1076:
1073:
1068:
1064:
1057:
1054:
1041:
1034:
1027:
1024:
1019:
1013:
1009:
1002:
999:
994:
990:
986:
982:
975:
973:
969:
964:
960:
956:
952:
945:
942:
937:
933:
928:
923:
919:
915:
911:
907:
903:
896:
893:
888:
884:
879:
874:
869:
864:
860:
856:
852:
845:
842:
837:
833:
828:
823:
819:
815:
811:
807:
803:
796:
793:
786:
781:
778:
775:
774:
773:
767:
765:
763:
759:
755:
751:
747:
739:
737:
730:
728:
726:
725:
719:
715:
711:
707:
703:
695:
693:
691:
687:
683:
679:
675:
671:
638:
633:
628:
622:
618:
615:
613:
605:
603:
601:
597:
589:
587:
583:
581:
577:
573:
569:
565:
561:
553:
551:
547:
545:
537:
535:
533:
529:
525:
515:
508:
502:
493:
488:
484:
477:
468:
464:
457:
450:
446:
445:
443:
440:
435:
428:
426:
422:
389:
387:
383:
378:
374:
370:
367:
365:
363:ECHA InfoCard
359:
351:
347:
346:DTXSID2045498
343:
342:
340:
331:
327:
320:
316:
315:
313:
311:
307:
300:
296:
295:
293:
291:
287:
280:
276:
275:
273:
271:
267:
260:
256:
255:
253:
251:
247:
240:
236:
235:
233:
231:
227:
220:
216:
215:
213:
211:
207:
200:
196:
195:
193:
186:
182:
175:
171:
170:
168:
166:
162:
153:
149:
142:
137:
133:
131:
127:
123:
119:
111:
106:
103:
102:
100:
98:
94:
90:
86:
84:
80:
76:
72:
70:
66:
62:
58:
56:
52:
49:Clinical data
47:
43:
38:
30:
19:
3851:Chloroarenes
3797:
3777:Ketoconazole
3774:Antagonists:
3773:
3747:Troglitazone
3722:Tetracycline
3711:
3677:Spiroxatrine
3622:Quingestrone
3617:Progesterone
3602:Pregnenolone
3597:Pregnanolone
3587:Pregnanediol
3582:Prednisolone
3507:Mifepristone
3434:
3409:Griseofulvin
3389:Fenbendazole
3374:Famprofazone
3369:Erythromycin
3364:Epothilone B
3349:Eburnamonine
3244:Clotrimazole
3234:Clofenvinfos
3169:Antimycotics
3100:
3063:Okadaic acid
3015:Antagonists:
3014:
3003:Troglitazone
2938:Mifepristone
2933:Methoxychlor
2928:Griseofulvin
2923:Ellagic acid
2903:Cypermethrin
2893:Clotrimazole
2844:
2723:tea tree oil
2708:lemon myrtle
2621:ethylparaben
2551:griseofulvin
2412:Benzylamines
2301:ravuconazole
2296:albaconazole
2288:voriconazole
2283:posaconazole
2273:itraconazole
2263:hexaconazole
2239:
2181:neticonazole
2171:luliconazole
2166:ketoconazole
2156:flutrimazole
2141:eberconazole
2131:clotrimazole
2116:butoconazole
1999:
1985:Furazolidone
1975:Policresulen
1895:
1878:Flutrimazole
1863:Butoconazole
1843:Ketoconazole
1813:Clotrimazole
1773:Sulfonamides
1735:Oxyquinoline
1545:
1539:
1514:
1510:
1504:
1477:
1473:
1463:
1431:(1): 40–79.
1428:
1424:
1414:
1387:
1383:
1373:
1361:. Retrieved
1356:
1347:
1322:
1318:
1311:
1276:
1270:
1235:
1231:
1221:
1204:
1200:
1166:
1162:
1156:
1137:
1131:
1119:. Retrieved
1115:the original
1110:
1100:
1081:
1075:
1066:
1062:
1056:
1044:. Retrieved
1039:
1026:
1007:
1001:
984:
980:
954:
950:
944:
909:
905:
895:
858:
854:
844:
809:
805:
795:
771:
761:
757:
750:ketoconazole
743:
734:
722:
699:
673:
669:
647:
616:
609:
593:
590:Interactions
584:
572:dysmenorrhea
557:
554:Side effects
548:
543:
541:
538:Medical uses
523:
522:
511:
505:
29:
3836:Piperazines
3762:Zafirlukast
3732:Thiothixene
3712:Terconazole
3662:Simvastatin
3537:Nisoldipine
3532:Nilvadipine
3517:Nicardipine
3487:Metacycline
3314:Dimercaprol
3269:Demecolcine
3229:Clindamycin
3224:Ciglitazone
3174:Artemisinin
3154:Ambrisentan
3058:Nigramide J
2993:Telmisartan
2953:Nicardipine
2863:Benfuracarb
2858:Artemisinin
2763:from market
2742:pentamidine
2703:lemon grass
2661:taurolidine
2631:polynoxylin
2532:flucytosine
2476:caspofungin
2400:terbinafine
2386:Allylamines
2248:fluconazole
2240:terconazole
2235:fluconazole
2206:tioconazole
2201:sulconazole
2191:oxiconazole
2186:omoconazole
2161:isoconazole
2136:croconazole
2094:inhibitors)
2092:demethylase
2049:Antifungals
1896:Terconazole
1873:Oxiconazole
1868:Omoconazole
1853:Azanidazole
1838:Tioconazole
1833:Isoconazole
1791:Antifungals
1758:Acetic acid
1753:Lactic acid
1725:Dequalinium
1703:derivatives
1667:Clindamycin
1662:Mepartricin
1657:Carfecillin
1629:Antibiotics
1616:antiseptics
596:nonoxynol-9
524:Terconazole
432: g·mol
369:100.061.573
139:Identifiers
83:MedlinePlus
55:Trade names
34:Terconazole
3821:Dioxolanes
3815:Categories
3742:Tianeptine
3707:Tenylidone
3702:Tacrolimus
3647:Rimexolone
3637:Rifampicin
3577:Plicamycin
3562:Paclitaxel
3547:Omeprazole
3527:Nifedipine
3502:Mevastatin
3497:Metyrapone
3477:Lovastatin
3472:Loratadine
3429:Hyperforin
3419:Haloprogin
3384:Felodipine
3359:Enzacamene
3339:Dronabinol
3304:Diclazuril
3283:prasterone
3239:Chloroxine
3214:Cephradine
3184:Bile acids
2998:Tolnaftate
2963:Permethrin
2948:Nevirapine
2943:Nefazodone
2912:prasterone
2873:Carvedilol
2853:Amiodarone
2824:modulators
2732:atovaquone
2713:orange oil
2676:tolnaftate
2671:tolciclate
2656:sulbentine
2626:haloprogin
2606:ciclopirox
2571:tavaborole
2563:inhibitors
2549:Systemic:
2530:Systemic:
2491:rezafungin
2486:micafungin
2481:cilofungin
2465:Systemic:
2459:inhibitors
2442:amorolfine
2421:butenafine
2378:inhibitors
2362:Systemic:
2339:ergosterol
2246:Systemic:
2176:miconazole
2126:climbazole
2111:bifonazole
2102:Imidazoles
2078:inhibitors
2075:Ergosterol
1995:Protiofate
1965:Clodantoin
1940:Ciclopirox
1828:Ornidazole
1818:Miconazole
1800:Imidazoles
1715:Clioquinol
1672:Pentamycin
1647:Hachimycin
1637:Candicidin
1069:(1): 1–17.
787:References
731:Metabolism
714:zymosterol
706:lanosterol
637:DE 2804096
528:antifungal
437:3D model (
425:Molar mass
319:ChEMBL1306
299:CHEBI:9451
259:0KJ2VE664U
230:ChemSpider
174:67915-31-5
165:CAS Number
148:IUPAC name
3667:Sirolimus
3657:Ritonavir
3652:Riodipine
3642:Rifaximin
3627:Reserpine
3612:Proadifen
3557:Oxatomide
3512:Nafcillin
3482:Meclizine
3344:Droxidopa
3324:Docetaxel
3249:Colforsin
3199:Bumecaine
3189:Bithionol
3101:Agonists:
3078:T-0901317
3053:Meclizine
2983:Reserpine
2973:Phenytoin
2958:Octicizer
2918:Efavirenz
2845:Agonists:
2773:Phase III
2761:Withdrawn
2718:patchouli
2666:ticlatone
2569:Topical:
2440:Topical:
2419:Topical:
2395:naftifine
2393:Topical:
2366:, hamycin
2354:natamycin
2347:Topical:
2320:abafungin
2318:Topical:
2311:Thiazoles
2294:Unknown:
2228:Topical:
2221:Triazoles
2146:econazole
2109:Topical:
1980:Nifuratel
1919:Natamycin
1888:Triazoles
1823:Econazole
1701:Quinoline
1691:Acetarsol
1684:compounds
1406:220575082
606:Chemistry
560:headaches
75:Monograph
69:Drugs.com
3794:See also
3682:SR-12813
3572:Piperine
3552:Orlistat
3522:Nicotine
3394:Fentanyl
3379:Febantel
3354:Ecopipam
3319:Dinaline
3204:Cafestol
3194:Bosentan
3068:PK-11195
2616:dimazole
2359:nystatin
2341:binding)
2067:membrane
1914:Nystatin
1906:Polyenes
1496:14748798
936:32845024
887:11220485
678:triazole
514:(verify)
210:DrugBank
97:ATC code
3782:Sesamin
3767:Zeranol
3697:Suramin
3467:LOE-908
3159:AMI-193
3073:S-07662
2988:TCPOBOP
2883:Chrysin
2737:dapsone
2349:hamycin
1970:Inosine
1682:Arsenic
1531:6834396
1455:9880474
1363:10 July
1339:3129389
1303:3288361
1262:3069196
1213:2677363
1183:6834396
1121:10 July
1046:10 July
993:2381618
963:1460451
927:8095055
878:1784691
836:3729366
758:Candida
740:History
704:enzyme
600:condoms
568:itching
544:Candida
386:Formula
219:DB00251
185:PubChem
113:)
107: (
105:G01AG02
89:a688022
59:Terazol
18:Terazol
3289:DHEA-S
3129:AA-861
2756:WHO-EM
2584:Others
2434:Others
2086:Azoles
1552:
1529:
1494:
1453:
1443:
1404:
1337:
1301:
1291:
1260:
1253:358042
1250:
1211:
1181:
1144:
1088:
1014:
991:
961:
934:
924:
885:
875:
834:
827:180489
824:
710:CYP3A4
642:
576:chills
526:is an
463:SMILES
430:532.47
310:ChEMBL
279:D00888
239:390122
199:441383
2888:CITCO
2065:Wall/
1958:Other
1933:Other
1446:88906
1402:S2CID
1036:(PDF)
680:with
612:ketal
580:fever
483:InChI
439:JSmol
290:ChEBI
134:94.9%
3460:and
3279:DHEA
3043:AITC
2908:DHEA
2055:and
1614:and
1550:ISBN
1527:PMID
1492:PMID
1451:PMID
1365:2015
1335:PMID
1299:PMID
1289:ISBN
1258:PMID
1209:PMID
1179:PMID
1142:ISBN
1123:2015
1086:ISBN
1048:2015
1012:ISBN
989:PMID
959:PMID
932:PMID
910:2020
883:PMID
832:PMID
718:NADH
564:rash
270:KEGG
250:UNII
124:data
65:AHFS
3089:PXR
2833:CAR
2728:PCP
2057:J02
2053:D01
1620:G01
1519:doi
1482:doi
1441:PMC
1433:doi
1392:doi
1327:doi
1281:doi
1248:PMC
1240:doi
1171:doi
922:PMC
914:doi
873:PMC
863:doi
822:PMC
814:doi
674:cis
335:EPA
189:CID
110:WHO
3817::
2769::
2730::
1525:.
1515:26
1513:.
1490:.
1478:10
1476:.
1472:.
1449:.
1439:.
1429:12
1427:.
1423:.
1400:.
1386:.
1382:.
1355:.
1333:.
1323:21
1321:.
1297:.
1287:.
1256:.
1246:.
1234:.
1230:.
1205:34
1203:.
1191:^
1177:.
1167:26
1165:.
1109:.
1067:22
1065:.
1038:.
985:76
983:.
971:^
955:79
953:.
930:.
920:.
908:.
904:.
881:.
871:.
857:.
853:.
830:.
820:.
810:29
808:.
804:.
656:Cl
654:31
650:26
602:.
578:,
574:,
566:,
403:Cl
400:31
394:26
3295:)
3291:(
3285:)
3281:(
2914:)
2910:(
2813:e
2806:t
2799:v
2520:/
2493:)
2469:(
2337:(
2088:(
2059:)
2051:(
2041:e
2034:t
2027:v
1622:)
1618:(
1601:e
1594:t
1587:v
1558:.
1533:.
1521::
1498:.
1484::
1457:.
1435::
1408:.
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1388:3
1367:.
1341:.
1329::
1305:.
1283::
1264:.
1242::
1236:1
1215:.
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1173::
1150:.
1125:.
1094:.
1050:.
1020:.
995:.
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938:.
916::
889:.
865::
859:8
838:.
816::
670:H
666:3
664:O
662:5
660:N
658:2
652:H
441:)
418:3
415:O
412:5
409:N
406:2
397:H
391:C
337:)
333:(
67:/
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
