802:
benzothiophene ring in sertaconazole mimics tryptophan and increases the drugs ability to form pores in the fungal cell membrane. If the cell membrane is made sufficiently leaky by these pores the fungal cell will die from loss of ATP and other effects which can include calcium disregulation. These pores are believed to open at about 10 minutes following topical application of sertaconazole. One hour following topical application, approximately 90% of fungal cells die from lack of energy (due to ATP loss) and general loss of homeostasis. Sertaconazole is thought to be the only benzothiophene antifungal with this mechanism of action.
906:
889:
476:
38:
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Sertaconazole has also antiinflammatory and antipruritic action. It inhibits the release of proinflammatory cytokines from activated immune cells. It has been shown that sertaconazole activates the p38/COX2/PGE2 pathway. PGE2 can have a variety of important effects in the body including activation of
801:
Chemically, sertaconazole contains a benzothiophene ring which makes it unique from other imidazole antifungals. A benzothiophene ring is a sulfur analogue of the indole ring found in the amino acid tryptophan. Tryptophan is found in the fungal membrane in addition to lipids such as ergosterol. The
675:
In randomized, double-blind, multicentre trials of 3 to 6 weeks' duration (n=127-383), a significantly greater number of patients with tinea of the glabrous skin and tinea pedis receiving a topical 2% sertaconazole cream once or twice daily achieved a successful mycological cure compared with
797:
Like other imidazole antifungals, sertaconazole blocks the synthesis of ergosterol by inhibiting the 14α-demethylase enzyme. Ergosterol is a critical component of the fungal cell membrane. Inhibition of ergosterol synthesis prevents fungal cells from multiplying and impairs hyphae growth.
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Sertaconazole also has antibacterial action. It is hypothesized that the mechanism of action again involves sertaconazole's ability to form pores by mimicking tryptophan.
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938:
Croxtall JD, Plosker GL (2009). "Sertaconazole: a review of its use in the management of superficial mycoses in dermatology and gynaecology".
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InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2
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Rote Liste 2017 – Arzneimittelverzeichnis für
Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte)
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Sertaconazole also appears to inhibit the dimorphic transformation of
Candida albicans into pathogenic fungi.
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The following fungal organisms, among others, are known to be susceptible to sertaconazole:
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984:. Vol. 57. Frankfurt/Main: Rote Liste Service GmbH (Hrsg.). 2017. p. 217.
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It has also been shown that sertaconazole can kill
Trichomonas vaginalis
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1363:
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Sertaconazole has several known mechanisms of action. It is considered
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were rarely reported with sertaconazole therapy, but may include
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Sertaconazole contains a stereocenter and consists of two
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816:. The exact mechanism of action is as yet unknown.
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667:form. The most popular of these is Gyno-Dermofix.
691:, burning on application site and skin dryness.
315:
290:
577:Clc1ccc(c(Cl)c1)C(OCc2c3cccc(Cl)c3sc2)Cn4ccnc4
123:
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8:
110:
19:
738:. Unsourced material may be challenged and
213:In general: ℞ (Prescription only)
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758:Learn how and when to remove this message
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269:)-1-{2--2-(2,4-dichlorophenyl)ethyl}-1
18:
1857:Lanosterol 14α-demethylase inhibitors
443:
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7:
1028:. U.S. National Library of Medicine.
1016:. U.S. National Library of Medicine.
736:adding citations to reliable sources
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952:10.2165/00003495-200969030-00009
904:
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1538:thymidylate synthase inhibitors
864:. The pharmaceutical drug is a
676:recipients of a placebo cream.
602:Key:JLGKQTAYUIMGRK-UHFFFAOYSA-N
524:
521:
497:
1:
882:Enantiomers of sertaconazole
645:class. It is available as a
633:, sold under the brand name
868:, an equal mixture of the (
842:Trichophyton mentagrophytes
806:the body's fever response.
1873:
660:It is also available in a
487:Chemical and physical data
1852:Phenylethanolamine ethers
1842:Chlorobenzene derivatives
1765:
1606:bromochlorosalicylanilide
1576:Aminoacyl tRNA synthetase
881:
610:
585:
565:
253:
55:Ertaczo, Dermofix, Zalain
35:
26:
835:Epidermophyton floccosum
1026:Drug Information Portal
1022:"Sertaconazole nitrate"
1014:Drug Information Portal
917:CAS number: 583057-51-6
900:CAS number: 583057-48-1
1390:Squalene monooxygenase
1227:Systemic: ketoconazole
1418:Systemic: terbinafine
639:antifungal medication
16:Antifungal medication
1706:Whitfield's ointment
1533:Pyrimidine analogues
1349:Polyene antimycotics
732:improve this section
637:among others, is an
849:Trichophyton rubrum
653:infections such as
23:
1792:Never to phase III
1696:tribromometacresol
1666:sodium thiosulfate
1661:selenium disulfide
1557:Mitotic inhibitors
689:contact dermatitis
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1471:β-glucan synthase
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556:Interactive image
456:CompTox Dashboard
244:>99% to plasma
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1701:undecylenic acid
1651:potassium iodide
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915:)-Sertaconazole
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898:)-Sertaconazole
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788:antitrichomonal
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1512:ibrexafungerp
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1293:oteseconazole
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1283:isavuconazole
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1245:efinaconazole
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1211:sertaconazole
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1166:fenticonazole
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1136:chlormidazole
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129:Sertaconazole
126:
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113:
112:Sertaconazole
108:
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68:
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45:Clinical data
43:
39:
34:
30:
25:
21:Sertaconazole
1847:Chloroarenes
1738:tea tree oil
1723:lemon myrtle
1636:ethylparaben
1566:griseofulvin
1427:Benzylamines
1316:ravuconazole
1311:albaconazole
1303:voriconazole
1298:posaconazole
1288:itraconazole
1278:hexaconazole
1210:
1196:neticonazole
1186:luliconazole
1181:ketoconazole
1171:flutrimazole
1156:eberconazole
1146:clotrimazole
1131:butoconazole
1025:
1013:
981:
976:
943:
939:
933:
912:
895:
873:
869:
859:
847:
840:
833:
826:
821:
818:
813:
811:
808:
804:
800:
796:
792:antipruritic
769:
754:
745:
730:Please help
718:
695:Pharmacology
685:Side effects
683:
680:Side effects
674:
671:Medical uses
659:
634:
630:
629:
618:
612:
270:
266:
194:Legal status
188:Legal status
93:License data
1778:from market
1757:pentamidine
1718:lemon grass
1676:taurolidine
1646:polynoxylin
1547:flucytosine
1491:caspofungin
1415:terbinafine
1401:Allylamines
1263:fluconazole
1255:terconazole
1250:fluconazole
1221:tioconazole
1216:sulconazole
1206:oxiconazole
1201:omoconazole
1176:isoconazole
1151:croconazole
1109:inhibitors)
1107:demethylase
1064:Antifungals
862:enantiomers
772:fungistatic
539: g·mol
425:CHEBI:82866
249:Identifiers
79:MedlinePlus
51:Trade names
1831:Categories
1747:atovaquone
1728:orange oil
1691:tolnaftate
1686:tolciclate
1671:sulbentine
1641:haloprogin
1621:ciclopirox
1586:tavaborole
1578:inhibitors
1564:Systemic:
1545:Systemic:
1506:rezafungin
1501:micafungin
1496:cilofungin
1480:Systemic:
1474:inhibitors
1457:amorolfine
1436:butenafine
1393:inhibitors
1377:Systemic:
1354:ergosterol
1261:Systemic:
1191:miconazole
1141:climbazole
1126:bifonazole
1117:Imidazoles
1093:inhibitors
1090:Ergosterol
925:References
776:fungicidal
748:April 2014
544:3D model (
532:Molar mass
377:72W71I16EG
348:ChemSpider
292:99592-32-2
283:CAS Number
258:IUPAC name
234:Negligible
1788:Phase III
1776:Withdrawn
1733:patchouli
1681:ticlatone
1584:Topical:
1455:Topical:
1434:Topical:
1410:naftifine
1408:Topical:
1381:, hamycin
1369:natamycin
1362:Topical:
1335:abafungin
1333:Topical:
1326:Thiazoles
1309:Unknown:
1243:Topical:
1236:Triazoles
1161:econazole
1124:Topical:
968:195684055
876:)-forms.
856:Chemistry
719:does not
649:to treat
140:Routes of
71:Monograph
65:Drugs.com
1821:Medicine
1631:dimazole
1374:nystatin
1356:binding)
1082:membrane
960:19275277
872:)- and (
866:racemate
814:in vitro
621:(verify)
328:DrugBank
154:ATC code
107:DailyMed
1752:dapsone
1364:hamycin
740:removed
725:sources
662:vaginal
641:of the
635:Ertaczo
493:Formula
337:DB01153
303:PubChem
174: (
172:G01AF19
170:)
164: (
162:D01AC14
147:Topical
127::
109::
85:a608047
1807:Portal
1771:WHO-EM
1599:Others
1449:Others
1101:Azoles
988:
966:
958:
790:, and
665:tablet
570:SMILES
537:437.76
436:ChEMBL
405:D08510
397:D06883
209:℞-only
207:
122:
105:
1080:Wall/
964:S2CID
940:Drugs
647:cream
590:InChI
546:JSmol
416:ChEBI
357:59273
317:65863
1070:and
986:ISBN
956:PMID
723:any
721:cite
651:skin
388:KEGG
368:UNII
224:data
61:AHFS
1743:PCP
1072:J02
1068:D01
948:doi
734:by
461:EPA
307:CID
177:WHO
167:WHO
125:FDA
1833::
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954:.
944:69
942:.
794:.
786:,
782:,
778:,
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657:.
510:Cl
507:15
501:20
267:RS
203:US
119:US
102:US
1809::
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1484:(
1352:(
1103:(
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1066:(
1056:e
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994:.
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913:S
911:(
896:R
894:(
874:S
870:R
761:)
755:(
750:)
746:(
742:.
728:.
548:)
525:S
522:O
519:2
516:N
513:3
504:H
498:C
463:)
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271:H
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205::
180:)
63:/
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