Bifonazole (trade name Canespor among others[: Bifonazole.]) is an imidazole antifungal drug used in form of ointments.
It was patented in 1974 and approved for medical use in 1983.
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
and distinguishes bifonazole from other antifungal drugs.
Pharmacokinetics
Six hours after application, bifonazole concentrations range from 1000
Microgram/
Cubic centimetre in the
stratum corneum to 5 μg/cm
3 in the
papillary dermis.
Synthesis
Friedel-Crafts acylation between
biphenyl (1) and
benzoyl chloride (2) gives 4-phenylbenzophenone (3). Reduction with sodium borohydride gives the alcohol (4). Halogenation by
thionyl chloride gives (5). Amination with
imidazole (6) completes the synthesis of bifonazole.
Further reading
