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Bifonazole

Bifonazole is an imidazole antifungal that also exhibits anticancer activity. Bifonazole inhibits calmodulin, HMG-CoA reductase, and 14-α demethylase in fungi such as dermatophytes. Bifonazole also decreases cell viability and induces Ca2+-dependent apoptosis in prostate cancer cells and melanoma cells.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18844251

Cas No.

60628-96-8

Purity

≥98%

Formula

C22H18N2

Formula Wt.

310.39

Chemical Name

1-([1,1-Biphenyl]-4-yl-phenylmethyl)-1H-imidazole

IUPAC Name

1-[phenyl-(4-phenylphenyl)methyl]imidazole

Synonym

Amycor; Bedriol; Mycospor; Mycosporan

Melting Point

142°C

Solubility

Soluble in alcohols, DMF or DMSO.

Appearance

White or Almost White Powder

Cheng JS, Chou CT, Liang WZ, et al. The mechanism of bifonazole-induced [Ca2+]i rises and non-Ca2+-triggered cell death in PC3 human prostate cancer cells. J Recept Signal Transduct Res. 2014 May 22:1-7. PMID: 24849495.

Penso J, Beitner R. Clotrimazole and bifonazole detach hexokinase from mitochondria of melanoma cells. Eur J Pharmacol. 1998 Jan 19;342(1):113-7. PMID: 9544799.

Hegemann L, Toso SM, Lahijani KI, et al. Direct interaction of antifungal azole-derivatives with calmodulin: a possible mechanism for their therapeutic activity. J Invest Dermatol. 1993 Mar;100(3):343-6. PMID: 8440921.

Berg D, Regel E, Harenberg HE, et al. Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung. 1984;34(2):139-46. PMID: 6372801.

Kawakami K, Harada T, Yoshihashi Y, et al. Correlation between glass-forming ability and fragility of pharmaceutical compounds. J Phys Chem B. 2015 Apr 9;119(14):4873-4880. PMID: 25781503.

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