Fenticonazole (original) (raw)

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Chemical compound

Pharmaceutical compound

Fenticonazole
Clinical data
Trade names Lomexin, Gynoxin
AHFS/Drugs.com International Drug Names
Routes of administration Topical (ovule, spray, cream)
ATC code D01AC12 (WHO) G01AF12 (WHO)
Legal status
Legal status UK: POM (Prescription only) US: Not approved In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)phenyl]methoxy}ethyl]-1_H_-imidazole
CAS Number 72479-26-6 checkY
PubChem CID 51755
ChemSpider 46840 ☒N
UNII QG05NRB077
KEGG D02582 checkY
ChEBI CHEBI:82863 ☒N
CompTox Dashboard (EPA) DTXSID7057812 Edit this at Wikidata
Chemical and physical data
Formula C24H20Cl2N2OS
Molar mass 455.40 g·mol−1
3D model (JSmol) Interactive image
SMILES c1ccc(cc1)Sc2ccc(cc2)COC(Cn3ccnc3)c4ccc(cc4Cl)Cl
InChI InChI=1S/C24H20Cl2N2OS/c25-19-8-11-22(23(26)14-19)24(15-28-13-12-27-17-28)29-16-18-6-9-21(10-7-18)30-20-4-2-1-3-5-20/h1-14,17,24H,15-16H2 ☒NKey:ZCJYUTQZBAIHBS-UHFFFAOYSA-N ☒N
☒NcheckY (what is this?) (verify)

Fenticonazole is an imidazole antifungal drug, used locally as the nitrate in the treatment of vulvovaginal candidiasis. It is active against a range of organisms including dermatophyte pathogens, Malassezia furfur, and Candida albicans. Fenticonazole has also been shown to exhibit antibacterial action, with a spectrum of activity that includes bacteria commonly associated with superinfected fungal skin and vaginal infections, and antiparasitic action against the protozoan Trichomonas vaginalis.[1]

Uses and administration

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A 200 mg pessary is inserted into the vagina at bedtime for 3 nights or a 600 mg pessary is inserted once only at bedtime. The fenticonazole nitrate vaginal capsule is not greasy, does not soil and can easily be removed with water.[2] Fenticonazole nitrate can also be applied topically as a 2% cream or solution for the treatment of fungal skin infections.[_citation needed_]

Pregnancy and lactation

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Oral administration of fenticonazole in rats has been reported to produce prolonged gestation and embryotoxic effects after doses above 40 mg/kg/day. Fenticonazole does not interfere with the function of male and female gonads and does not modify the first phases of reproduction. Fenticonazole has shown no teratogenic effects in rats and rabbits. Fenticonazole or its metabolites cross the placental barrier in pregnant rats and rabbits after vaginal application and are excreted in milk of lactating rats. Since there is no experience of use during pregnancy or lactation, fenticonazole nitrate vaginal capsules should not be used unless the physician considers if essential to the welfare of the patient.[2]

Burning and itching have been reported after the application of fenticonazole nitrate.[_citation needed_]

Intravaginal preparations of fenticonazole may damage latex contraceptives and additional contraceptive measures are therefore necessary during local administration.[_citation needed_]

  1. ^ Veraldi S, Milani R (2008). "Topical fenticonazole in dermatology and gynaecology: current role in therapy". Drugs. 68 (15): 2183–2194. doi:10.2165/00003495-200868150-00007. PMID 18840006. S2CID 46971075.
  2. ^ a b Stewart M (20 October 2020). Dajani S (ed.). "Fenticonazole for vaginal thrush". Patient. Egton Medical Information Systems Limited.