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 ;
ECHA InfoCard	100.056.651
Chemical and physical data
Formula	C22H18N2
Molar mass	310.392 g/mol
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 many others^[1]) is an imidazole antifungal drug used in form of ointments.

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.^[2]

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.^[2]^[3]

Pharmacokinetics

Six hours after application, bifonazole concentrations range from 1000 µg/cm³ in the stratum corneum to 5 µg/cm³ in the papillary dermis.^[2]

References

↑ International Drug Names: Bifonazole.
1 2 3 Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Canesten Bifonazol-Creme.
↑ Berg, D; Regel, E; Harenberg, H. E.; Plempel, M (1984). "Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole". Arzneimittel-Forschung. 34 (2): 139–46. PMID 6372801.

Lackner, T. E.; Clissold, S. P. (1989). "Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses". Drugs. 38 (2): 204–25. doi:10.2165/00003495-198938020-00004. PMID 2670516.

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[1] International Drug Names: Bifonazole.

[AC-2] 1 2 3 Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Canesten Bifonazol-Creme.

[3] Berg, D; Regel, E; Harenberg, H. E.; Plempel, M (1984). "Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole". Arzneimittel-Forschung. 34 (2): 139–46. PMID 6372801.