Bifonazole
- D01AC10 (WHO)
- In general: Over-the-counter (OTC)
- (RS)-1-[Phenyl(4-phenylphenyl)methyl]-1H-imidazole
- 60628-96-8 Y
- 2378
- DB04794 Y
- 2287 Y
- QYJ305Z91O
- D01775 Y
- CHEBI:31286 N
- ChEMBL277535 Y
- DTXSID9045631
- Interactive image
- n1ccn(c1)C(c3ccc(c2ccccc2)cc3)c4ccccc4
- 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
Bifonazole (trade name Canespor among others[1]) is an imidazole antifungal drug used in form of ointments.
It was patented in 1974 and approved for medical use in 1983.[2] 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.[3] Bifonazole is a potent aromatase inhibitor in vitro.[4][5]
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.[3][6]
Pharmacokinetics
Six hours after application, bifonazole concentrations range from 1000 μg/cm3 in the stratum corneum to 5 μg/cm3 in the papillary dermis.[3]
References
- ^ International Drug Names: Bifonazole.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495.
- ^ a b c Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Canesten Bifonazol-Creme.
- ^ Trösken ER, Fischer K, Völkel W, Lutz WK (February 2006). "Inhibition of human CYP19 by azoles used as antifungal agents and aromatase inhibitors, using a new LC-MS/MS method for the analysis of estradiol product formation". Toxicology. 219 (1–3): 33–40. doi:10.1016/j.tox.2005.10.020. PMID 16330141.
- ^ Egbuta C, Lo J, Ghosh D (December 2014). "Mechanism of inhibition of estrogen biosynthesis by azole fungicides". Endocrinology. 155 (12): 4622–4628. doi:10.1210/en.2014-1561. PMC 4239419. PMID 25243857.
- ^ Berg D, Regel E, Harenberg HE, Plempel M (1984). "Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole". Arzneimittel-Forschung. 34 (2): 139–146. PMID 6372801.
Further reading
- Lackner TE, Clissold SP (August 1989). "Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses". Drugs. 38 (2): 204–225. doi:10.2165/00003495-198938020-00004. PMID 2670516. S2CID 195697559.
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Ergosterol inhibitors |
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β-glucan synthase inhibitors |
Pyrimidine analogues/ thymidylate synthase inhibitors |
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Mitotic inhibitors |
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Aminoacyl tRNA synthetase inhibitors |
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- bromochlorosalicylanilide
- chlorophetanol
- chlorphenesin
- ciclopirox
- crystal violet
- dimazole
- ethylparaben
- haloprogin‡
- polynoxylin
- potassium iodide#
- salicylic acid
- selenium disulfide#
- sodium thiosulfate#
- sulbentine
- taurolidine
- ticlatone
- tolciclate
- tolnaftate
- tribromometacresol
- undecylenic acid
- Whitfield's ointment#
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III