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 Y
PubChem CID	2378
DrugBank	DB04794 Y
ChemSpider	2287 Y
UNII	QYJ305Z91O
KEGG	D01775 Y
ChEBI	CHEBI:31286 N
ChEMBL	ChEMBL277535 Y
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 Y Key:OCAPBUJLXMYKEJ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Bifonazole (trade name Canespor among others) is an imidazole antifungal drug used in form of ointments.

It was patented in 1974 and approved for medical use in 1983. 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. Bifonazole is a potent aromatase inhibitor in vitro.

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.

Pharmacokinetics

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

Further reading