Bifonazole

Bifonazole
Clinical data
Trade names	Canespor, many others
AHFS/Drugs.com	International Drug Names
Routes of; administration	Topical
ATC code	D01AC10 (WHO) ;
Legal status
Legal status	In general: Over-the-counter (OTC);
Identifiers
	IUPAC name (RS)-1-[Phenyl(4-phenylphenyl)methyl]-1H-imidazole;
CAS Number	60628-96-8 ;
PubChem CID	2378;
DrugBank	DB04794 ;
ChemSpider	2287 ;
UNII	QYJ305Z91O;
KEGG	D01775 ;
ChEBI	CHEBI:31286 ;
ChEMBL	ChEMBL277535 ;
CompTox Dashboard (EPA)	DTXSID9045631 ;
ECHA InfoCard	100.056.651
Chemical and physical data
Formula	C22H18N2
Molar mass	310.400 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES n1ccn(c1)C(c3ccc(c2ccccc2)cc3)c4ccccc4;
	InChI InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H ; Key:OCAPBUJLXMYKEJ-UHFFFAOYSA-N ;
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Bifonazole (trade name Canespor among others[1]) is an imidazole antifungal drug used in form of ointments.

It was patented in 1974 and approved for medical use in 1983.[2] There are also combinations with carbamide for the treatment of onychomycosis.

Adverse effects

The most common side effect is a burning sensation at the application site. Other reactions, such as itching, eczema or skin dryness, are rare.[3] Bifonazole is a potent aromatase inhibitor in vitro.[4][5]

Pharmacology

Mechanism of action

Bifonazole has a dual mode of action. It inhibits fungal ergosterol biosynthesis at two points, via transformation of 24-methylendihydrolanosterol to desmethylsterol, together with inhibition of HMG-CoA. This enables fungicidal properties against dermatophytes and distinguishes bifonazole from other antifungal drugs.[3][6]

Pharmacokinetics

Six hours after application, bifonazole concentrations range from 1000 µg/cm³ in the stratum corneum to 5 µg/cm³ in the papillary dermis.[3]

References

International Drug Names: Bifonazole.
Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495.
Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Canesten Bifonazol-Creme.
Trösken ER, Fischer K, Völkel W, Lutz WK (February 2006). "Inhibition of human CYP19 by azoles used as antifungal agents and aromatase inhibitors, using a new LC-MS/MS method for the analysis of estradiol product formation". Toxicology. 219 (1–3): 33–40. doi:10.1016/j.tox.2005.10.020. PMID 16330141.
Egbuta C, Lo J, Ghosh D (December 2014). "Mechanism of inhibition of estrogen biosynthesis by azole fungicides". Endocrinology. 155 (12): 4622–4628. doi:10.1210/en.2014-1561. PMC 4239419. PMID 25243857.
Berg D, Regel E, Harenberg HE, Plempel M (1984). "Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole". Arzneimittel-Forschung. 34 (2): 139–146. PMID 6372801.