Fenticonazole

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 ℞ (Prescription only)
Identifiers
IUPAC name 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)phenyl]methoxy}ethyl]-1H-imidazole
CAS Number	72479-26-6^Y
PubChem (CID)	51755
ChemSpider	46840^N
UNII	QG05NRB077^Y
KEGG	D02582^Y
ChEBI	CHEBI:82863^N
Chemical and physical data
Formula	C₂₄H₂₀Cl₂N₂OS
Molar mass	455.4 g/mol
3D model (Jmol)	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^N Key:ZCJYUTQZBAIHBS-UHFFFAOYSA-N^N
^NY (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.

Uses and administration

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. Fenticonazole nitrate is also applied topically as a 2% cream or solution for the treatment of fungal skin infections.

Adverse effects

Burning and itching have been reported after the application of fenticonazole nitrate.

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

References

The Merck Index, 12th Edition. 4047

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ clotrimazole^# croconazole^‡ econazole fenticonazole^‡ flutrimazole isoconazole^‡ ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

Triazoles	Topical: efinaconazole fluconazole^# fosfluconazole terconazole Systemic: fluconazole^# hexaconazole^‡ isavuconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡ ravuconazole^†

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine

Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole

Triazoles	Terconazole

Polyenes	Nystatin Natamycin Amphotericin B

Other	Ciclopirox Methylrosaniline

Other

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