Fenticonazole

Title: Fenticonazole
CAS Registry Number: 72479-26-6
CAS Name: 1-[2-(2,4-Dichlorophenyl)-2-[[4-(phenylthio)phenyl]methoxy]ethyl]-1H-imidazole
Additional Names: 1-[2,4-dichloro-b-[[p-(phenylthio)benzyl]oxy]phenethyl]imidazole; 1-(2,4-dichlorophenyl)-2-(N-imidazolyl)ethyl-4-phenylthiobenzyl ether; 2,4-dichloro-4¢-phenylthio-(N-imidazolylmethyl)dibenzyl ether
Molecular Formula: C24H20Cl2N2OS
Molecular Weight: 455.40
Percent Composition: C 63.30%, H 4.43%, Cl 15.57%, N 6.15%, O 3.51%, S 7.04%
Literature References: Broad spectrum antimycotic; also active as antibacterial. Prepn: D. Nardi et al., DE 2917244; eidem, US 4221803 (1979, 1980 both to Recordati); eidem, Arzneim.-Forsch. 31, 2123 (1981). Series of articles on physico-chemical properties, in vitro and in vivo antibacterial and antifungal activity, pharmacology and toxicology: ibid. 2127-2154. Toxicity data: G. Graziani et al., ibid. 2145. Preliminary clinical comparison with miconazole in vaginal candidiasis: A. Gastaldi, Curr. Ther. Res. 38, 489 (1985). Comparative clinical trials in dermatomycoses: A. Finzi et al., Mykosen 29, 41 (1986); E. M. Kokoschka et al., ibid. 45.
Derivative Type: Mononitrate
CAS Registry Number: 73151-29-8
Manufacturers' Codes: Rec-15-1476
Trademarks: Falvin (Farmades); Fentiderm (Zyma); Fentigyn (Novartis); Lomexin (Recordati)
Molecular Formula: C24H20Cl2NS.HNO3
Molecular Weight: 488.41
Percent Composition: C 59.02%, H 4.33%, Cl 14.52%, N 5.74%, S 6.57%, O 9.83%
Properties: Odorless, white crystalline powder, mp 136°. uv max (methanol): 252 nm (e 13894). Soly at 20° (mg/ml): water <0.1; ethyl ether <0.1; ethanol 30; methanol 100; chloroform 300; DMF 600. pKa 6.54. LD50 in mice, male rats, female rats (mg/kg): 1191, 440, 309 i.p.; all >3000 orally (Graziani).
Melting point: mp 136°
pKa: pKa 6.54
Absorption maximum: uv max (methanol): 252 nm (e 13894)
Toxicity data: LD50 in mice, male rats, female rats (mg/kg): 1191, 440, 309 i.p.; all >3000 orally (Graziani)
Therap-Cat: Antifungal (topical).
Keywords: Antifungal (Synthetic); Imidazoles.
Fentonium Bromide Fentrazamide Fenuron Fenvalerate Fepradinol

Fenticonazole
Fenticonazole.png
Systematic (IUPAC) name
1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)phenyl]methoxy}ethyl]-1H-imidazole
Clinical data
AHFS/Drugs.com International Drug Names
Legal status prescription
Routes ovule, spray, cream
Identifiers
CAS number 72479-26-6
ATC code D01AC12 G01AF12
PubChem CID 51755
UNII QG05NRB077 YesY
KEGG D02582 YesY
Chemical data
Formula C24H20Cl2N2OS 
Mol. mass 455.4 g/mol
 YesY (what is this?)  (verify)

Fenticonazole is an azole 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.