Bifonazole

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Bifonazole
Bifonazole.svg
Systematic (IUPAC) name
(RS)-1-[Phenyl(4-phenylphenyl)methyl]-1H-imidazole
Clinical data
Trade names Canespor, many others
AHFS/Drugs.com International Drug Names
Routes of
administration
Topical
Legal status
Legal status
Identifiers
CAS Number 60628-96-8 YesY
ATC code D01AC10 (WHO)
PubChem CID 2378
DrugBank DB04794 YesY
ChemSpider 2287 YesY
UNII QYJ305Z91O YesY
KEGG D01775 YesY
ChEBI CHEBI:31286 N
ChEMBL CHEMBL277535 YesY
Chemical data
Formula C22H18N2
Molar mass 310.392 g/mol
Chirality Racemic mixture
 NYesY (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.[1]

There are also combinations with carbamide for the treatment of onychomycosis.

Adverse effects[edit]

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[edit]

Mechanism of action[edit]

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.[2][3]

Pharmacokinetics[edit]

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[edit]

  1. ^ International Drug Names: Bifonazole.
  2. ^ a b c Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. 
  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.