Bifonazole

Bifonazole
Systematic (IUPAC) name

(RS)-1-[Phenyl(4-phenylphenyl)methyl]-1H-imidazole
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	US: OTC
Routes of administration	topic
Identifiers
CAS Number	60628-96-8^Y
ATC code	D01AC10
PubChem	CID 2378
DrugBank	DB04794^Y
ChemSpider	2287^Y
UNII	QYJ305Z91O^Y
KEGG	D01775^Y
ChEBI	CHEBI:31286^N
ChEMBL	CHEMBL277535^Y
Chemical data
Formula	C₂₂H₁₈N₂
Molar mass	310.392 g/mol
Chirality	1 : 1 mixture (racemate)
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 is an imidazole antifungal drug. Bifonazole is marketed by Bayer under the trade mark Canespor in ointment form.

Mechanism of action

Bifonazole has dual mode of action. It blocks transformation of 24-methylendihydrolanosterol to desmethylsterol in fungi together with inhibition of HMG-CoA. This enables fungicidal properties against dermatophytes and distinguishes bifonazole from other antifungal drugs.

References

External links

Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. / Drugs. 1989 Aug;38(2):204-25. PMID 2670516

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ chlormidazole^‡ croconazole^‡ fenticonazole^‡ isoconazole^‡ luliconazole neticonazole^‡ omoconazole^‡ butoconazole clotrimazole^# econazole ketoconazole miconazole^# oxiconazole sertaconazole sulconazole tioconazole

Triazoles	Topical: fluconazole^#, fosfluconazole efinaconazole terconazole Systemic: hexaconazole^‡ isavuconazole fluconazole itraconazole posaconazole voriconazole Unknown: albaconazole^‡

Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Allylamines
(squalene monooxygenase
inhibitors)

Topical: amorolfine^‡
butenafine
naftifine
terbinafine
Systemic: terbinafine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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