539:
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.
737:, 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
362:
339:
725:
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.
610:
31:
705:: 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
523:. 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.
574:
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
709:
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.
538:
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
724:
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
741:, 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.
701:. 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
1305:
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".
1588:
2800:
437:
661:-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:
1581:
938:
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".
479:
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
681:. 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.
531:
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
749:
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
1574:
1031:. 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
85:
606:
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.
2793:
571:
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.
495:
3814:
2786:
53:
451:
1498:
Heeres J, Hendrickx R, Van Cutsem J (April 1983). "Antimycotic azoles. 6. Synthesis and antifungal properties of terconazole, a novel triazole ketal".
1150:
Heeres J, Hendrickx R, Van Cutsem J (April 1983). "Antimycotic azoles. 6. Synthesis and antifungal properties of terconazole, a novel triazole ketal".
629:
1095:
1050:
Faro S, Apuzzio J, Bohannon N, Elliott K, Martens MG, Mou SM, et al. (March 1997). "Treatment
Considerations in Vulvovaginal Candidiasis".
2744:
2028:
1542:
1281:
1078:
1004:
710:
Terconazole targets fungi specifically since humans do not use lanosterol in this pathway. This process does not affect all fungi such as
968:
Schmitt C, Sobel J, Meriwether C (September 1990). "Comparison of 0.8% and 1.6% terconazole cream in severe vulvovaginal candidiasis".
3844:
1134:
706:
471:
3595:
2820:
1127:
Kucers' the Use of
Antibiotics Sixth Edition: a Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs
136:
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2511:
891:"Oral versus intra-vaginal imidazole and triazole anti-fungal treatment of uncomplicated vulvovaginal candidiasis (thrush)"
3829:
2078:
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at 1300 °C (2372 °F) to give many different types of triazole derivatives. These are purified using alcohol and
3834:
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238:
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developed it in 1983. Previously, all triazole based drugs targeted fungal infections related to plants from
2749:
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1989:
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Grayson ML, Crowe SM, McCarthy JS, Mills J, Mouton JW, Norrby SR, Paterson DL, Pfaller MA, eds. (2010).
1103:
742:
3112:
3102:
1188:
Cauwenbergh G, Vanden
Bossche H (August 1989). "Terconazole. Pharmacology of a new antimycotic agent".
307:
1566:
995:
Maibach HI, Farage MA, eds. (2006). "Vulvar
Therapies: Evidence vs. Testimony. Fungal: Candidiasis.".
625:
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3412:
3107:
3031:
3006:
2014:
889:
Denison HJ, Worswick J, Bond CM, Grimshaw JM, Mayhew A, Gnani
Ramadoss S, et al. (August 2020).
789:
Tolman EL, Isaacson DM, Rosenthale ME, McGuire JL, Van Cutsem J, Borgers M, et al. (June 1986).
3809:
3446:
3252:
3152:
3076:
2506:
2322:
1894:
761:
Terconazole is a white, odourless powder. It can be purchased commercially in the following forms:
334:
153:
2876:
840:"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.
43:
3455:
3061:
2976:
587:. A precipitate is formed upon combination of both drugs. Terconazole may weaken latex-based
287:
3715:
3435:
3317:
3247:
3132:
3122:
3117:
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1978:
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1264:
Yoshida Y (1988). "Cytochrome P450 of Fungi: Primary Target for Azole
Antifungal Agents".
690:
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361:
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1129:(6th ed.). Boca Raton, FL: CRC Press. Taylor & Francis Group. pp. 1933–5.
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63:
559:, burning or discomfort. Other side effects may include abdominal pain or cramps,
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1604:
1022:"Sexually Transmitted Diseases Treatment Guidelines, 2010. Vol. 59. No. RR-12"
856:
702:
694:
620:
615:
535:
species. It also shows effectiveness against dermatomycoses in animal models.
516:
413:
218:
1021:
657:. The chemical name for terconazole is 1-{methyl}-1,3-dioxolan-2-yl]methyl}-1
3655:
3645:
3640:
3630:
3615:
3600:
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2006:
1968:
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1073:(2nd ed.). Burlington, MA: Jones & Bartlett Learning. p. 312.
57:
22:
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999:(1st ed.). New York: Informa Healthcare USA, Inc. pp. 128–129.
806:
666:
548:
198:
1511:
1425:
1232:
1163:
768:
Terconazole 0.8% cream 5 g applied intravaginally once a day for 3 days;
765:
Terconazole 0.4% cream 5 g applied intravaginally once a day for 7 days;
207:
3770:
3755:
3685:
3147:
2871:
2725:
2337:
1958:
1670:
753:
It is still used as a treatment in cases of resistance to other drugs.
173:
791:"Anticandidal activities of terconazole, a broad-spectrum antimycotic"
771:
Terconazole 80 mg vaginal suppository used once daily for 3 days.
698:
665:- methyl benzoate and the sodium salt of triazole, created by mixing
588:
564:
298:
1537:(3rd ed.). St. Louis, Missouri: Elsevier. pp. 1558–1559.
267:
2074:
608:
600:
568:
436:
427:
278:
556:
552:
258:
2782:
2010:
1570:
1562:
Information about terconazole from the United States
Government
1217:"Overview of medically important antifungal azole derivatives"
459:
Clc1ccc(c(Cl)c1)4(O(COc3ccc(N2CCN(C(C)C)CC2)cc3)CO4)Cn5ncnc5
323:
1533:
Mosby (2012). "Terconazole". In White K, Watrous J (eds.).
1071:
Frequently Prescribed Medications: Drugs You Need to Know
2821:
603:
with broad-spectrum antifungal/antimycotic tendencies.
502:
733:
In 1940, the first commercial antifungal drug, called
1408:
Sheehan DJ, Hitchcock CA, Sibley CM (January 1999).
689:
Terconazole binds to the heme iron component on the
547:
The most common side effects of terconazole include
3075:
2819:
2572:
2548:
2529:
2505:
2498:
2443:
2422:
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127:
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84:
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52:
42:
37:
673:. These are put in a solution and catalyzed using
1459:"History of the development of azole derivatives"
838:Sood G, Nyirjesy P, Weitz MV, Chatwani A (2000).
844:Infectious Diseases in Obstetrics and Gynecology
186:
161:
1410:"Current and emerging azole antifungal agents"
1183:
1181:
1102:. State Government of Victoria. Archived from
1029:USA Centers for Disease Control and Prevention
940:The Journal of the Florida Medical Association
2794:
2022:
1582:
1535:Mosby's Drug Reference for Health Professions
583:Terconazole may interact with the spermicide
8:
1020:Workowski KA, Berman S (December 17, 2010).
997:The Vulva: Anatomy, Physiology and Pathology
21:
3077:
895:The Cochrane Database of Systematic Reviews
3128:Allopregnanedione (5α-dihydroprogesterone)
2801:
2787:
2779:
2502:
2370:
2086:
2070:
2059:
2029:
2015:
2007:
1784:
1589:
1575:
1567:
360:
337:
226:
144:1-methoxy]phenyl]-4-propan-2-yl-piperazine
1474:
1433:
1384:
1348:. Stanford University, Stanford, CA 94305
1308:The Journal of Antimicrobial Chemotherapy
1240:
963:
961:
914:
865:
855:
814:
246:
2826:Tooltip Constitutive androstane receptor
1373:Infectious Diseases in Clinical Practice
781:
476:
456:
333:
206:
141:
76:
3581:Pregnanedione (5β-dihydroprogesterone)
2967:Pregnanedione (5β-dihydroprogesterone)
637:Terconazole has the chemical formula C
351:
20:
3815:Lanosterol 14α-demethylase inhibitors
795:Antimicrobial Agents and Chemotherapy
306:
286:
62:
7:
1190:The Journal of Reproductive Medicine
97:
1463:Clinical Microbiology and Infection
1342:"C-4 Methylsterol Oxidase Activity"
266:
177:
1266:Current Topics in Medical Mycology
14:
1268:. Vol. 2. pp. 388–418.
1069:Mancano MA, Gallagher JC (2013).
1476:10.1111/j.1470-9465.2004.00841.x
1386:10.1097/00019048-199409000-00002
1369:"Mini Review. Candida Vaginitis"
1094:Melbourne Sexual Health Centre.
397:
391:
385:
29:
2512:thymidylate synthase inhibitors
484:Key:BLSQLHNBWJLIBQ-OZXSUGGESA-N
3133:Allopregnanolone (brexanolone)
1500:Journal of Medicinal Chemistry
1152:Journal of Medicinal Chemistry
907:10.1002/14651858.CD002845.pub3
403:
379:
1:
3788:Receptor/signaling modulators
3746:Tropanyl 3,5-dimethulbenzoate
3596:Pregnenolone 16α-carbonitrile
1414:Clinical Microbiology Reviews
1346:Saccharomyces Genome Database
1221:Clinical Microbiology Reviews
551:, vulvar/vaginal irritation,
1274:10.1007/978-1-4612-3730-3_11
3323:Dodecylbenzenesulfonic acid
3082:Tooltip Pregnane X receptor
2810:Xenobiotic-sensing receptor
1215:Fromtling RA (April 1988).
3861:
1457:Maertens JA (March 2004).
716:, which lacks lanosterol.
599:Terconazole is a triazole
369:Chemical and physical data
3845:Phenylethanolamine ethers
3779:
2739:
2580:bromochlorosalicylanilide
2550:Aminoacyl tRNA synthetase
970:Obstetrics and Gynecology
857:10.1155/S1064744900000351
492:
467:
447:
132:
28:
3706:Testosterone isocaproate
3621:Reverse triiodothyronine
697:of fungi, also known as
3098:17α-Hydroxyprogesterone
3093:17α-Hydroxypregnenolone
1990:Lactobacillus fermentum
613:Terconazole synthesis:
521:vaginal yeast infection
2364:Squalene monooxygenase
2201:Systemic: ketoconazole
1699:Diiodohydroxyquinoline
713:Pneumocystis jirovecii
634:
2837:6,7-Dimethylesculetin
2392:Systemic: terbinafine
1100:Better Health Channer
743:Janssen Pharmaceutica
621:U.S. patent 4,223,036
616:U.S. patent 4,144,346
612:
3830:Triazole antifungals
3424:Hypericum perforatum
3413:Hetacillin potassium
2680:Whitfield's ointment
2507:Pyrimidine analogues
2323:Polyene antimycotics
1320:10.1093/jac/21.3.333
1196:(8 Suppl): 588–592.
807:10.1128/aac.29.6.986
3835:Isopropyl compounds
3253:Cyproterone acetate
3153:Amlodipine besylate
1512:10.1021/jm00358a032
1426:10.1128/cmr.12.1.40
1233:10.1128/CMR.1.2.187
1164:10.1021/jm00358a032
976:(3 Pt 1): 414–416.
685:Mechanism of action
519:drug used to treat
25:
3726:Thonzonium bromide
3481:Methylprednisolone
3282:prasterone sulfate
2766:Never to phase III
2670:tribromometacresol
2640:sodium thiosulfate
2635:selenium disulfide
2531:Mitotic inhibitors
1052:The Female Patient
635:
3797:
3796:
3431:Indinavir sulfate
3138:Alpha-Lipoic acid
3113:Δ-Androstenedione
3103:Δ-Androstenedione
2776:
2775:
2568:
2567:
2494:
2493:
2445:β-glucan synthase
2439:
2438:
2418:
2417:
2317:
2316:
2004:
2003:
1942:
1941:
1544:978-0-323-09574-7
1469:(Suppl 1): 1–10.
1367:Sobel JD (1994).
1283:978-1-4612-8323-2
1106:on 5 October 2015
1080:978-1-4496-9884-3
1006:978-0-8493-3608-9
510:
509:
438:Interactive image
319:CompTox Dashboard
16:Chemical compound
3852:
3716:Thiamylal sodium
3451:γ-linolenic acid
3447:α-Linolenic acid
3445:Linolenic acid:
3436:Lasalocid sodium
3426:(St John's wort)
3318:Docusate calcium
3248:Cyclophosphamide
3123:Allopregnanediol
3108:Δ-Androstenediol
3083:
3079:
3037:Ethinylestradiol
2887:Cyclophosphamide
2827:
2823:
2803:
2796:
2789:
2780:
2675:undecylenic acid
2625:potassium iodide
2503:
2371:
2087:
2071:
2060:
2031:
2024:
2017:
2008:
1934:Methylrosaniline
1785:
1591:
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1111:
1096:"Vaginal thrush"
1091:
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1084:
1066:
1060:
1059:
1047:
1041:
1040:
1038:
1036:
1026:
1017:
1011:
1010:
992:
986:
985:
965:
956:
955:
935:
929:
928:
918:
886:
880:
879:
869:
859:
850:(5–6): 240–243.
835:
829:
828:
818:
786:
751:Aspergillus spp.
675:dimethyl sulfate
633:
632:
628:
623:
618:
506:
505:
498:
440:
420:
405:
399:
393:
387:
381:
364:
353:
342:
341:
327:
325:
310:
290:
270:
250:
230:
210:
190:
180:
179:
165:
101:
80:
66:
33:
26:
24:
3860:
3859:
3855:
3854:
3853:
3851:
3850:
3849:
3800:
3799:
3798:
3793:
3775:
3676:Suberoylanilide
3393:Fluorometholone
3288:Dibunate sodium
3168:Aurothioglucose
3081:
3071:
3007:3,17β-Estradiol
2825:
2815:
2807:
2777:
2772:
2771:
2756:Clinical trials
2735:
2564:
2544:
2525:
2510:
2490:
2447:
2435:
2414:
2395:
2391:
2366:
2358:
2350:
2325:
2313:
2294:
2247:fosravuconazole
2204:
2080:
2079:lanosterol 14α-
2066:
2055:
2049:
2035:
2005:
2000:
1979:Povidone-iodine
1938:
1917:
1889:
1871:
1774:
1756:
1728:
1684:
1665:
1641:Oxytetracycline
1631:Chloramphenicol
1612:
1601:anti-infectives
1595:
1558:
1553:
1552:
1545:
1532:
1531:
1527:
1497:
1496:
1492:
1456:
1455:
1451:
1407:
1406:
1402:
1366:
1365:
1361:
1351:
1349:
1340:
1339:
1335:
1304:
1303:
1299:
1284:
1263:
1262:
1258:
1214:
1213:
1209:
1187:
1186:
1179:
1149:
1148:
1144:
1137:
1124:
1123:
1119:
1109:
1107:
1093:
1092:
1088:
1081:
1068:
1067:
1063:
1049:
1048:
1044:
1034:
1032:
1024:
1019:
1018:
1014:
1007:
994:
993:
989:
967:
966:
959:
946:(10): 693–696.
937:
936:
932:
901:(8): CD002845.
888:
887:
883:
837:
836:
832:
788:
787:
783:
778:
759:
757:Available forms
731:
722:
691:cytochrome P450
687:
656:
652:
648:
644:
640:
630:
624:
619:
614:
597:
581:
545:
529:
501:
499:
496:(what is this?)
493:
488:
485:
480:
475:
474:
463:
460:
455:
454:
443:
418:
408:
402:
396:
390:
384:
345:
321:
313:
293:
273:
253:
233:
213:
193:
176:
168:
148:
145:
140:
139:
119:Protein binding
111:Pharmacokinetic
105:
17:
12:
11:
5:
3858:
3856:
3848:
3847:
3842:
3837:
3832:
3827:
3822:
3817:
3812:
3802:
3801:
3795:
3794:
3792:
3791:
3784:
3780:
3777:
3776:
3774:
3773:
3768:
3759:
3758:
3753:
3748:
3743:
3741:Troleandomycin
3738:
3733:
3728:
3723:
3718:
3713:
3708:
3703:
3698:
3693:
3688:
3683:
3678:
3673:
3668:
3663:
3661:Spironolactone
3658:
3653:
3648:
3643:
3638:
3633:
3628:
3623:
3618:
3613:
3608:
3603:
3598:
3593:
3588:
3583:
3578:
3573:
3568:
3563:
3558:
3553:
3548:
3543:
3538:
3533:
3531:Norelgestromin
3528:
3523:
3518:
3513:
3508:
3503:
3498:
3493:
3488:
3483:
3478:
3473:
3468:
3463:
3458:
3453:
3443:
3438:
3433:
3428:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3388:Flucloxacillin
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3290:
3285:
3275:
3265:
3260:
3255:
3250:
3245:
3243:Corticosterone
3240:
3235:
3230:
3225:
3220:
3215:
3210:
3208:Chlorpromazine
3205:
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3160:
3155:
3150:
3145:
3140:
3135:
3130:
3125:
3120:
3115:
3110:
3105:
3100:
3095:
3086:
3084:
3073:
3072:
3070:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3029:
3027:17-Androstanol
3024:
3022:3β-Androstanol
3019:
3017:3α-Androstenol
3014:
3012:3α-Androstanol
3009:
3000:
2999:
2994:
2989:
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2919:
2914:
2909:
2904:
2894:
2889:
2884:
2879:
2874:
2869:
2867:Chlorpromazine
2864:
2859:
2854:
2849:
2844:
2839:
2830:
2828:
2817:
2816:
2808:
2806:
2805:
2798:
2791:
2783:
2774:
2773:
2770:
2769:
2768:
2767:
2764:
2753:
2747:
2741:
2740:
2737:
2736:
2734:
2733:
2728:
2723:
2714:
2709:
2704:
2699:
2694:
2689:
2687:citronella oil
2683:
2682:
2677:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2637:
2632:
2630:salicylic acid
2627:
2622:
2617:
2612:
2607:
2602:
2600:crystal violet
2597:
2592:
2587:
2585:chlorophetanol
2582:
2576:
2574:
2570:
2569:
2566:
2565:
2563:
2562:
2555:
2553:
2546:
2545:
2543:
2542:
2535:
2533:
2527:
2526:
2524:
2523:
2516:
2514:
2500:
2496:
2495:
2492:
2491:
2489:
2488:
2483:
2477:
2472:
2467:
2462:
2451:
2449:
2441:
2440:
2437:
2436:
2434:
2433:
2426:
2424:
2420:
2419:
2416:
2415:
2413:
2412:
2405:
2403:
2397:
2396:
2394:
2393:
2386:
2379:
2377:
2368:
2360:
2359:
2357:
2356:
2353:amphotericin B
2345:
2340:
2333:
2331:
2319:
2318:
2315:
2314:
2312:
2311:
2304:
2302:
2296:
2295:
2293:
2292:
2287:
2280:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2242:fosfluconazole
2239:
2232:
2231:
2226:
2221:
2214:
2212:
2206:
2205:
2203:
2202:
2198:
2197:
2192:
2187:
2182:
2177:
2172:
2167:
2162:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2122:
2117:
2112:
2107:
2102:
2095:
2093:
2084:
2068:
2057:
2051:
2050:
2036:
2034:
2033:
2026:
2019:
2011:
2002:
2001:
1999:
1998:
1993:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1950:
1948:
1944:
1943:
1940:
1939:
1937:
1936:
1931:
1925:
1923:
1919:
1918:
1916:
1915:
1913:Amphotericin B
1910:
1905:
1899:
1897:
1891:
1890:
1888:
1887:
1881:
1879:
1873:
1872:
1870:
1869:
1864:
1859:
1854:
1849:
1844:
1839:
1834:
1829:
1824:
1819:
1814:
1809:
1804:
1799:
1793:
1791:
1782:
1776:
1775:
1773:
1772:
1766:
1764:
1758:
1757:
1755:
1754:
1749:
1744:
1738:
1736:
1730:
1729:
1727:
1726:
1721:
1719:Broxyquinoline
1716:
1711:
1709:Chlorquinaldol
1706:
1701:
1695:
1693:
1686:
1685:
1683:
1682:
1676:
1674:
1667:
1666:
1664:
1663:
1658:
1653:
1648:
1643:
1638:
1633:
1628:
1622:
1620:
1614:
1613:
1596:
1594:
1593:
1586:
1579:
1571:
1565:
1564:
1557:
1556:External links
1554:
1551:
1550:
1543:
1525:
1506:(4): 611–613.
1490:
1449:
1400:
1379:(5): 334–339.
1359:
1333:
1314:(3): 333–343.
1297:
1282:
1256:
1227:(2): 187–217.
1207:
1177:
1158:(4): 611–613.
1142:
1136:978-0340927670
1135:
1117:
1086:
1079:
1061:
1042:
1012:
1005:
987:
957:
930:
881:
830:
801:(6): 986–991.
780:
779:
777:
774:
773:
772:
769:
766:
758:
755:
735:amphotericin B
730:
727:
721:
718:
686:
683:
679:chromatography
671:sodium hydride
654:
650:
646:
642:
638:
596:
593:
580:
577:
544:
541:
528:
525:
508:
507:
490:
489:
487:
486:
483:
481:
478:
470:
469:
468:
465:
464:
462:
461:
458:
450:
449:
448:
445:
444:
442:
441:
433:
431:
423:
422:
416:
410:
409:
406:
400:
394:
388:
382:
377:
371:
370:
366:
365:
355:
347:
346:
344:
343:
330:
328:
315:
314:
312:
311:
303:
301:
295:
294:
292:
291:
283:
281:
275:
274:
272:
271:
263:
261:
255:
254:
252:
251:
243:
241:
235:
234:
232:
231:
223:
221:
215:
214:
212:
211:
203:
201:
195:
194:
192:
191:
183:
181:
170:
169:
167:
166:
158:
156:
150:
149:
147:
146:
143:
135:
134:
133:
130:
129:
125:
124:
121:
115:
114:
107:
106:
104:
103:
90:
88:
82:
81:
74:
68:
67:
60:
50:
49:
46:
40:
39:
35:
34:
15:
13:
10:
9:
6:
4:
3:
2:
3857:
3846:
3843:
3841:
3838:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3820:Phenol ethers
3818:
3816:
3813:
3811:
3808:
3807:
3805:
3790:
3789:
3785:
3782:
3781:
3778:
3772:
3769:
3767:
3764:
3761:
3760:
3757:
3754:
3752:
3749:
3747:
3744:
3742:
3739:
3737:
3734:
3732:
3729:
3727:
3724:
3722:
3719:
3717:
3714:
3712:
3709:
3707:
3704:
3702:
3699:
3697:
3694:
3692:
3689:
3687:
3684:
3682:
3681:Sulfisoxazole
3679:
3677:
3674:
3672:
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3627:
3624:
3622:
3619:
3617:
3614:
3612:
3609:
3607:
3604:
3602:
3599:
3597:
3594:
3592:
3589:
3587:
3584:
3582:
3579:
3577:
3574:
3572:
3569:
3567:
3564:
3562:
3559:
3557:
3556:Phenobarbital
3554:
3552:
3549:
3547:
3544:
3542:
3539:
3537:
3534:
3532:
3529:
3527:
3524:
3522:
3519:
3517:
3514:
3512:
3509:
3507:
3504:
3502:
3499:
3497:
3494:
3492:
3489:
3487:
3484:
3482:
3479:
3477:
3474:
3472:
3469:
3467:
3464:
3462:
3459:
3457:
3454:
3452:
3448:
3444:
3442:
3441:Levothyroxine
3439:
3437:
3434:
3432:
3429:
3427:
3425:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3403:Guggulsterone
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3298:Dicloxacillin
3296:
3294:
3291:
3289:
3286:
3283:
3279:
3276:
3273:
3269:
3266:
3264:
3263:Dexamethasone
3261:
3259:
3256:
3254:
3251:
3249:
3246:
3244:
3241:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3198:Cephaloridine
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3161:
3159:
3156:
3154:
3151:
3149:
3146:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3088:
3087:
3085:
3080:
3074:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3002:
3001:
2998:
2997:Valproic acid
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2957:Phenobarbital
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2902:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2857:Carbamazepine
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2832:
2831:
2829:
2824:
2818:
2814:
2811:
2804:
2799:
2797:
2792:
2790:
2785:
2784:
2781:
2765:
2763:
2760:
2759:
2757:
2754:
2751:
2748:
2746:
2743:
2742:
2738:
2732:
2729:
2727:
2724:
2722:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2684:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2590:chlorphenesin
2588:
2586:
2583:
2581:
2578:
2577:
2575:
2571:
2561:
2557:
2556:
2554:
2551:
2547:
2541:
2537:
2536:
2534:
2532:
2528:
2522:
2518:
2517:
2515:
2513:
2508:
2504:
2501:
2499:Intracellular
2497:
2487:
2486:ibrexafungerp
2484:
2481:
2478:
2476:
2473:
2471:
2468:
2466:
2463:
2461:
2460:anidulafungin
2457:
2456:echinocandins
2453:
2452:
2450:
2446:
2442:
2432:
2428:
2427:
2425:
2421:
2411:
2407:
2406:
2404:
2402:
2398:
2390:
2387:
2385:
2381:
2380:
2378:
2376:
2372:
2369:
2365:
2361:
2354:
2349:
2346:
2344:
2341:
2339:
2335:
2334:
2332:
2329:
2324:
2320:
2310:
2306:
2305:
2303:
2301:
2297:
2291:
2288:
2286:
2282:
2281:
2278:
2275:
2273:
2270:
2268:
2267:oteseconazole
2265:
2263:
2260:
2258:
2257:isavuconazole
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2234:
2233:
2230:
2227:
2225:
2222:
2220:
2219:efinaconazole
2216:
2215:
2213:
2211:
2207:
2200:
2199:
2196:
2193:
2191:
2188:
2186:
2185:sertaconazole
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2140:fenticonazole
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2116:
2113:
2111:
2110:chlormidazole
2108:
2106:
2103:
2101:
2097:
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2085:
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2076:
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2025:
2020:
2018:
2013:
2012:
2009:
1997:
1996:Copper usnate
1994:
1992:
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1878:
1874:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1847:Propenidazole
1845:
1843:
1840:
1838:
1837:Fenticonazole
1835:
1833:
1830:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1797:Metronidazole
1795:
1794:
1792:
1790:
1786:
1783:
1781:
1777:
1771:
1770:Sulfatolamide
1768:
1767:
1765:
1763:
1759:
1753:
1752:Ascorbic acid
1750:
1748:
1745:
1743:
1740:
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1735:
1734:Organic acids
1731:
1725:
1722:
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1599:
1598:Gynecological
1592:
1587:
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1578:
1573:
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1569:
1563:
1560:
1559:
1555:
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1234:
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1184:
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1173:
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1105:
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1057:
1053:
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1030:
1023:
1016:
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1008:
1002:
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988:
983:
979:
975:
971:
964:
962:
958:
953:
949:
945:
941:
934:
931:
926:
922:
917:
912:
908:
904:
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868:
863:
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853:
849:
845:
841:
834:
831:
826:
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808:
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800:
796:
792:
785:
782:
775:
770:
767:
764:
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748:
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740:
736:
728:
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719:
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684:
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536:
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522:
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491:
482:
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457:
453:
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434:
432:
429:
424:
417:
415:
411:
378:
376:
372:
367:
363:
359:
356:
354:
352:ECHA InfoCard
348:
340:
336:
335:DTXSID2045498
332:
331:
329:
320:
316:
309:
305:
304:
302:
300:
296:
289:
285:
284:
282:
280:
276:
269:
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264:
262:
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256:
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196:
189:
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164:
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159:
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155:
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142:
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112:
108:
100:
95:
92:
91:
89:
87:
83:
79:
75:
73:
69:
65:
61:
59:
55:
51:
47:
45:
41:
38:Clinical data
36:
32:
27:
19:
3840:Chloroarenes
3786:
3766:Ketoconazole
3763:Antagonists:
3762:
3736:Troglitazone
3711:Tetracycline
3700:
3666:Spiroxatrine
3611:Quingestrone
3606:Progesterone
3591:Pregnenolone
3586:Pregnanolone
3576:Pregnanediol
3571:Prednisolone
3496:Mifepristone
3423:
3398:Griseofulvin
3378:Fenbendazole
3363:Famprofazone
3358:Erythromycin
3353:Epothilone B
3338:Eburnamonine
3233:Clotrimazole
3223:Clofenvinfos
3158:Antimycotics
3089:
3052:Okadaic acid
3004:Antagonists:
3003:
2992:Troglitazone
2927:Mifepristone
2922:Methoxychlor
2917:Griseofulvin
2912:Ellagic acid
2892:Cypermethrin
2882:Clotrimazole
2833:
2712:tea tree oil
2697:lemon myrtle
2610:ethylparaben
2540:griseofulvin
2401:Benzylamines
2290:ravuconazole
2285:albaconazole
2277:voriconazole
2272:posaconazole
2262:itraconazole
2252:hexaconazole
2228:
2170:neticonazole
2160:luliconazole
2155:ketoconazole
2145:flutrimazole
2130:eberconazole
2120:clotrimazole
2105:butoconazole
1988:
1974:Furazolidone
1964:Policresulen
1884:
1867:Flutrimazole
1852:Butoconazole
1832:Ketoconazole
1802:Clotrimazole
1762:Sulfonamides
1724:Oxyquinoline
1534:
1528:
1503:
1499:
1493:
1466:
1462:
1452:
1420:(1): 40–79.
1417:
1413:
1403:
1376:
1372:
1362:
1350:. Retrieved
1345:
1336:
1311:
1307:
1300:
1265:
1259:
1224:
1220:
1210:
1193:
1189:
1155:
1151:
1145:
1126:
1120:
1108:. Retrieved
1104:the original
1099:
1089:
1070:
1064:
1055:
1051:
1045:
1033:. Retrieved
1028:
1015:
996:
990:
973:
969:
943:
939:
933:
898:
894:
884:
847:
843:
833:
798:
794:
784:
760:
750:
746:
739:ketoconazole
732:
723:
711:
688:
662:
658:
636:
605:
598:
582:
579:Interactions
573:
561:dysmenorrhea
546:
543:Side effects
537:
532:
530:
527:Medical uses
512:
511:
500:
494:
18:
3825:Piperazines
3751:Zafirlukast
3721:Thiothixene
3701:Terconazole
3651:Simvastatin
3526:Nisoldipine
3521:Nilvadipine
3506:Nicardipine
3476:Metacycline
3303:Dimercaprol
3258:Demecolcine
3218:Clindamycin
3213:Ciglitazone
3163:Artemisinin
3143:Ambrisentan
3047:Nigramide J
2982:Telmisartan
2942:Nicardipine
2852:Benfuracarb
2847:Artemisinin
2752:from market
2731:pentamidine
2692:lemon grass
2650:taurolidine
2620:polynoxylin
2521:flucytosine
2465:caspofungin
2389:terbinafine
2375:Allylamines
2237:fluconazole
2229:terconazole
2224:fluconazole
2195:tioconazole
2190:sulconazole
2180:oxiconazole
2175:omoconazole
2150:isoconazole
2125:croconazole
2083:inhibitors)
2081:demethylase
2038:Antifungals
1885:Terconazole
1862:Oxiconazole
1857:Omoconazole
1842:Azanidazole
1827:Tioconazole
1822:Isoconazole
1780:Antifungals
1747:Acetic acid
1742:Lactic acid
1714:Dequalinium
1692:derivatives
1656:Clindamycin
1651:Mepartricin
1646:Carfecillin
1618:Antibiotics
1605:antiseptics
585:nonoxynol-9
513:Terconazole
421: g·mol
358:100.061.573
128:Identifiers
72:MedlinePlus
44:Trade names
23:Terconazole
3810:Dioxolanes
3804:Categories
3731:Tianeptine
3696:Tenylidone
3691:Tacrolimus
3636:Rimexolone
3626:Rifampicin
3566:Plicamycin
3551:Paclitaxel
3536:Omeprazole
3516:Nifedipine
3491:Mevastatin
3486:Metyrapone
3466:Lovastatin
3461:Loratadine
3418:Hyperforin
3408:Haloprogin
3373:Felodipine
3348:Enzacamene
3328:Dronabinol
3293:Diclazuril
3272:prasterone
3228:Chloroxine
3203:Cephradine
3173:Bile acids
2987:Tolnaftate
2952:Permethrin
2937:Nevirapine
2932:Nefazodone
2901:prasterone
2862:Carvedilol
2842:Amiodarone
2813:modulators
2721:atovaquone
2702:orange oil
2665:tolnaftate
2660:tolciclate
2645:sulbentine
2615:haloprogin
2595:ciclopirox
2560:tavaborole
2552:inhibitors
2538:Systemic:
2519:Systemic:
2480:rezafungin
2475:micafungin
2470:cilofungin
2454:Systemic:
2448:inhibitors
2431:amorolfine
2410:butenafine
2367:inhibitors
2351:Systemic:
2328:ergosterol
2235:Systemic:
2165:miconazole
2115:climbazole
2100:bifonazole
2091:Imidazoles
2067:inhibitors
2064:Ergosterol
1984:Protiofate
1954:Clodantoin
1929:Ciclopirox
1817:Ornidazole
1807:Miconazole
1789:Imidazoles
1704:Clioquinol
1661:Pentamycin
1636:Hachimycin
1626:Candicidin
1058:(1): 1–17.
776:References
720:Metabolism
703:zymosterol
695:lanosterol
626:DE 2804096
517:antifungal
426:3D model (
414:Molar mass
308:ChEMBL1306
288:CHEBI:9451
248:0KJ2VE664U
219:ChemSpider
163:67915-31-5
154:CAS Number
137:IUPAC name
3656:Sirolimus
3646:Ritonavir
3641:Riodipine
3631:Rifaximin
3616:Reserpine
3601:Proadifen
3546:Oxatomide
3501:Nafcillin
3471:Meclizine
3333:Droxidopa
3313:Docetaxel
3238:Colforsin
3188:Bumecaine
3178:Bithionol
3090:Agonists:
3067:T-0901317
3042:Meclizine
2972:Reserpine
2962:Phenytoin
2947:Octicizer
2907:Efavirenz
2834:Agonists:
2762:Phase III
2750:Withdrawn
2707:patchouli
2655:ticlatone
2558:Topical:
2429:Topical:
2408:Topical:
2384:naftifine
2382:Topical:
2355:, hamycin
2343:natamycin
2336:Topical:
2309:abafungin
2307:Topical:
2300:Thiazoles
2283:Unknown:
2217:Topical:
2210:Triazoles
2135:econazole
2098:Topical:
1969:Nifuratel
1908:Natamycin
1877:Triazoles
1812:Econazole
1690:Quinoline
1680:Acetarsol
1673:compounds
1395:220575082
595:Chemistry
549:headaches
64:Monograph
58:Drugs.com
3783:See also
3671:SR-12813
3561:Piperine
3541:Orlistat
3511:Nicotine
3383:Fentanyl
3368:Febantel
3343:Ecopipam
3308:Dinaline
3193:Cafestol
3183:Bosentan
3057:PK-11195
2605:dimazole
2348:nystatin
2330:binding)
2056:membrane
1903:Nystatin
1895:Polyenes
1485:14748798
925:32845024
876:11220485
667:triazole
503:(verify)
199:DrugBank
86:ATC code
3771:Sesamin
3756:Zeranol
3686:Suramin
3456:LOE-908
3148:AMI-193
3062:S-07662
2977:TCPOBOP
2872:Chrysin
2726:dapsone
2338:hamycin
1959:Inosine
1671:Arsenic
1520:6834396
1444:9880474
1352:10 July
1328:3129389
1292:3288361
1251:3069196
1202:2677363
1172:6834396
1110:10 July
1035:10 July
982:2381618
952:1460451
916:8095055
867:1784691
825:3729366
747:Candida
729:History
693:enzyme
589:condoms
557:itching
533:Candida
375:Formula
208:DB00251
174:PubChem
102:)
96: (
94:G01AG02
78:a688022
48:Terazol
3278:DHEA-S
3118:AA-861
2745:WHO-EM
2573:Others
2423:Others
2075:Azoles
1541:
1518:
1483:
1442:
1432:
1393:
1326:
1290:
1280:
1249:
1242:358042
1239:
1200:
1170:
1133:
1077:
1003:
980:
950:
923:
913:
874:
864:
823:
816:180489
813:
699:CYP3A4
631:
565:chills
515:is an
452:SMILES
419:532.47
299:ChEMBL
268:D00888
228:390122
188:441383
2877:CITCO
2054:Wall/
1947:Other
1922:Other
1435:88906
1391:S2CID
1025:(PDF)
669:with
601:ketal
569:fever
472:InChI
428:JSmol
279:ChEBI
123:94.9%
3449:and
3268:DHEA
3032:AITC
2897:DHEA
2044:and
1603:and
1539:ISBN
1516:PMID
1481:PMID
1440:PMID
1354:2015
1324:PMID
1288:PMID
1278:ISBN
1247:PMID
1198:PMID
1168:PMID
1131:ISBN
1112:2015
1075:ISBN
1037:2015
1001:ISBN
978:PMID
948:PMID
921:PMID
899:2020
872:PMID
821:PMID
707:NADH
553:rash
259:KEGG
239:UNII
113:data
54:AHFS
3078:PXR
2822:CAR
2717:PCP
2046:J02
2042:D01
1609:G01
1508:doi
1471:doi
1430:PMC
1422:doi
1381:doi
1316:doi
1270:doi
1237:PMC
1229:doi
1160:doi
911:PMC
903:doi
862:PMC
852:doi
811:PMC
803:doi
663:cis
324:EPA
178:CID
99:WHO
3806::
2758::
2719::
1514:.
1504:26
1502:.
1479:.
1467:10
1465:.
1461:.
1438:.
1428:.
1418:12
1416:.
1412:.
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1371:.
1344:.
1322:.
1312:21
1310:.
1286:.
1276:.
1245:.
1235:.
1223:.
1219:.
1194:34
1192:.
1180:^
1166:.
1156:26
1154:.
1098:.
1056:22
1054:.
1027:.
974:76
972:.
960:^
944:79
942:.
919:.
909:.
897:.
893:.
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860:.
846:.
842:.
819:.
809:.
799:29
797:.
793:.
645:Cl
643:31
639:26
591:.
567:,
563:,
555:,
392:Cl
389:31
383:26
3284:)
3280:(
3274:)
3270:(
2903:)
2899:(
2802:e
2795:t
2788:v
2509:/
2482:)
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878:.
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805::
659:H
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647:2
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401:5
398:N
395:2
386:H
380:C
326:)
322:(
56:/
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