Bifonazole

Bifonazole

Systematic (IUPAC) name
(RS)-1-[Phenyl(4-phenylphenyl)methyl]-1H-imidazole
Clinical data
Trade names	Canespor, many others
AHFS/Drugs.com	International Drug Names
Legal status	OTC
Routes of administration	Topical
Identifiers
CAS Number	60628-96-8 Y
ATC code	D01AC10 (WHO)
PubChem	CID: 2378
DrugBank	DB04794 Y
ChemSpider	2287 Y
UNII	QYJ305Z91O Y
KEGG	D01775 Y
ChEBI	CHEBI:31286 N
ChEMBL	CHEMBL277535 Y
Chemical data
Formula	C22H18N2
Molecular mass	310.392 g/mol
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 Y Key:OCAPBUJLXMYKEJ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Bifonazole is an imidazole antifungal drug. Bifonazole is marketed by Bayer under the trade name Canespor in ointment form. Many other trade names exist.

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.

Pharmacology

Mechanism of action

Bifonazole has 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.

Pharmacokinetics

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