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

• ChemBase ID: 4340
• Molecular Formular: C22H18N2
• Molecular Mass: 310.39172
• Monoisotopic Mass: 310.14699859
• SMILES: n1(C(c2ccc(cc2)c2ccccc2)c2ccccc2)ccnc1
• Canonical SMILES: c1ccc(cc1)c1ccc(cc1)C(n1ccnc1)c1ccccc1
• 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
• InChIKey: OCAPBUJLXMYKEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[phenyl(4-phenylphenyl)methyl]-1H-imidazole
• IUPAC Traditional name: bifonazole; 1-[phenyl(4-phenylphenyl)methyl]-1H-imidazole
• Brand Name: Amycor; Azolmen; Mycospor
• Synonyms: (+-)-1-(p,alpha-Diphenylbenzyl)imidazole; (+-)1-([1,1'-Biphenyl]-4-ylphenylmethyl)-1H-imidazole; 1-((4-Biphenylyl)phenylmethyl)-1H-imidazole; 1-(alpha-(4-Biphenylyl)benzyl)imidazole; 1-(p,alpha-Diphenylbenzyl)imidazole; Bifonazol [inn-spanish]; Bifonazolum [inn-latin]; Trifonazole; Bay h 4502; Bifonazole; 1-[4,α-Diphenylbenzyl]-imidazole; 1-(p,α-Diphenylbenzyl)imidazole; Bifonazole; 1-(phenyl-(4-phenylphenyl)-methyl)imidazole; Bifazole; Mycospor; Mycosporan

Database IDs

• CAS Number: 60628-96-8
• EC Number: 262-336-6
• MDL Number: MFCD00865567
• PubChem SID: 46507284; 160967772
• PubChem CID: 2378

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.7149897
• LogD (pH = 7.4): 5.178793
• Log P: 5.2343907
• Molar Refractivity: 97.9411 cm^3
• Polarizability: 39.21749 Å^3
• Polar Surface Area: 17.82 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.92
• LOG S: -5.1
• Solubility (Water): 2.45e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder
• Hydrophobicity(logP): 4.77 [BIOBYTE (1995)]

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: NI3517000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22; R:22
• Safety Statements: S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Pharmacology Properties

• Mechanism of Action: Inhibitor of fungal cytochrome P450 enzyme 14-alpha-demethylase

Product Information

• Purity: ≥98% (HPLC); 97%
• Salt Data: Free Base
• Application(s): Topical antimycotic
• Empirical Formula (Hill Notation): C22H18N2

DETAILS

MP Biomedicals - 02154856

(1-[4,α-Diphenylbenzyl]-imidazole)

DrugBank - DB04794

• Drug Groups: approved
• Description: Bifonazole is an azole antifungal drug. [Wikipedia]
• Indication: Used for the treatment of various topical fungal infections, including athlete's foot (tinea pedis).
• Pharmacology: Bifonazole is a type of antifungal medicine known as an imidazole. It kills fungi and yeasts by interfering with their cell membranes.
• Affected Organisms: Fungi
• Biotransformation: Hepatic.
• Absorption: Very low absorption following topical administration (0.6% of an applied dose). In cases of skin lesions absorption is increased (2.5%).
• Half Life: 1-2 hours
• References: Watanabe S, Takahashi H, Nishikawa T, Takiuchi I, Higashi N, Nishimoto K, Kagawa S, Yamaguchi H, Ogawa H: A comparative clinical study between 2 weeks of luliconazole 1% cream treatment and 4 weeks of bifonazole 1% cream treatment for tinea pedis. Mycoses. 2006 May;49(3):236-41. [Pubmed] ; Cho KJ, Su W, Chen WC, Law YP, Fang HC, Liu CP, Cheng JS, Lee KC, Lo YK, Chang HT, Huang JK, Jan CR: Mechanism of bifonazole-induced [Ca2+]i increases in MDCK renal tubular cells. Chin J Physiol. 2001 Sep 30;44(3):97-101. [Pubmed] ; Tanuma H, Doi M, Sato N, Nishiyama S, Abe M, Kume H, Katsuoka K: Bifonazole (Mycospor cream) in the treatment of moccasin-type tinea pedis. Comparison between combination therapy of bifonazole cream + 10% urea ointment (Urepearl) and occlusive dressing therapy with the same agents. Mycoses. 2000;43(3-4):129-37. [Pubmed] ; Berg D, Regel E, Harenberg HE, Plempel M: Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung. 1984;34(2):139-46. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S1854

Research Area: Infection
Biological Activity:

Sigma Aldrich - B3563

Biochem/physiol Actions
Bifonazole is an imidazole-based anti-fungal agent with broad spectrum activity against many fungi, molds, yeast and some Gram-positive bacteria. Bifonazole inhibits ergosterol biosynthetic protein 28 and Cytochrome P450 2B4.

REFERENCES

• Watanabe S, Takahashi H, Nishikawa T, Takiuchi I, Higashi N, Nishimoto K, Kagawa S, Yamaguchi H, Ogawa H: A comparative clinical study between 2 weeks of luliconazole 1% cream treatment and 4 weeks of bifonazole 1% cream treatment for tinea pedis. Mycoses. 2006 May;49(3):236-41. Pubmed
• Cho KJ, Su W, Chen WC, Law YP, Fang HC, Liu CP, Cheng JS, Lee KC, Lo YK, Chang HT, Huang JK, Jan CR: Mechanism of bifonazole-induced [Ca2+]i increases in MDCK renal tubular cells. Chin J Physiol. 2001 Sep 30;44(3):97-101. Pubmed
• Tanuma H, Doi M, Sato N, Nishiyama S, Abe M, Kume H, Katsuoka K: Bifonazole (Mycospor cream) in the treatment of moccasin-type tinea pedis. Comparison between combination therapy of bifonazole cream + 10% urea ointment (Urepearl) and occlusive dressing therapy with the same agents. Mycoses. 2000;43(3-4):129-37. Pubmed
• Berg D, Regel E, Harenberg HE, Plempel M: Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung. 1984;34(2):139-46. Pubmed
• Ger. Pat., 1976, 2 461 406; CA, 85, 160095t, (synth, pharmacol)
• Schlueter, G. et al., Arzneim.-Forsch., 1983, 33, 739, (tox)
• Rieth, H., Int. Symp. Bifonazole, (Karger, Ed.), Basel, Switz., 1984, (book)
• Fromtling, R.A., Drugs of Today (Barcelona), 1985, 21, 401, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 319