Bifonazole (trade name Canespor among others) is an
imidazole
Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole Diazole refers ...
antifungal drug
An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryp ...
used in form of ointments.
It was patented in 1974 and approved for medical use in 1983.
There are also combinations with
carbamide
Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid.
Urea serves an important r ...
for the treatment of
onychomycosis
Onychomycosis, also known as tinea unguium, is a fungal infection of the nail. Symptoms may include white or yellow nail discoloration, thickening of the nail, and separation of the nail from the nail bed. Toenails or fingernails may be affected ...
.
Adverse effects
The most common side effect is a burning sensation at the application site. Other reactions, such as itching,
eczema
Dermatitis is inflammation of the Human skin, skin, typically characterized by itchiness, erythema, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become lichenification, thick ...
or skin dryness, are rare.
Bifonazole is a potent
aromatase inhibitor
Aromatase inhibitors (AIs) are a class of drugs used in the treatment of breast cancer in postmenopausal women and in men, and gynecomastia in men. They may also be used off-label to reduce estrogen conversion when supplementing testosterone exog ...
''
in vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...
''.
Pharmacology
Mechanism of action
Bifonazole has a dual
mode of action A mode of action (MoA) describes a functional or anatomical change, resulting from the exposure of a living organism to a substance. In comparison, a mechanism of action (MOA) describes such changes at the molecular level.
A mode of action is impor ...
. It inhibits fungal
ergosterol
Ergosterol (ergosta-5,7,22-trien-3β-ol) is a sterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Because many fungi and protozoa cannot survive without ergosterol, the ...
biosynthesis at two points, via transformation of
24-methylendihydrolanosterol to
desmethylsterol, together with inhibition of
HMG-CoA
β-Hydroxy β-methylglutaryl-CoA (HMG-CoA), also known as 3-hydroxy-3-methylglutaryl coenzyme A, is an intermediate in the mevalonate and ketogenesis pathways. It is formed from acetyl CoA and acetoacetyl CoA by HMG-CoA synthase. The research of M ...
. This enables fungicidal properties against
dermatophyte
Dermatophyte (from Greek '' derma'' "skin" (GEN ''dermatos'') and ''phyton'' "plant") is a common label for a group of fungus of ''Arthrodermataceae'' that commonly causes skin disease in animals and humans. Traditionally, these anamorphic (as ...
s and distinguishes bifonazole from other antifungal drugs.
Pharmacokinetics
Six hours after application, bifonazole concentrations range from 1000
µg
In the metric system, a microgram or microgramme is a unit of mass equal to one millionth () of a gram. The unit symbol is μg according to the International System of Units (SI); the recommended symbol in the United States and United Kingdom whe ...
/
cm³ in the
stratum corneum
The stratum corneum (Latin for 'horny layer') is the outermost layer of the epidermis. The human stratum corneum comprises several levels of flattened corneocytes that are divided into two layers: the ''stratum disjunctum'' and ''stratum compact ...
to 5 µg/cm³ in the
papillary dermis
The dermis or corium is a layer of skin between the epidermis (with which it makes up the cutis) and subcutaneous tissues, that primarily consists of dense irregular connective tissue and cushions the body from stress and strain. It is divided in ...
.
References
Further reading
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{{Antifungals
21-Hydroxylase inhibitors
Imidazole antifungals
Biphenyls
Antifungals
Aromatase inhibitors
CYP17A1 inhibitors
Lanosterol 14α-demethylase inhibitors