Bifonazole
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MedKoo CAT#: 317325

CAS#: 60628-96-8

Description: Bifonazole is an imidazole antifungal drug. 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. Bifonazole is marketed by Bayer under the trade mark Canespor in ointment form.


Chemical Structure

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Bifonazole
CAS# 60628-96-8

Theoretical Analysis

MedKoo Cat#: 317325
Name: Bifonazole
CAS#: 60628-96-8
Chemical Formula: C22H18N2
Exact Mass: 310.147
Molecular Weight: 310.39
Elemental Analysis: C, 85.13; H, 5.85; N, 9.03

Price and Availability

Size Price Availability Quantity
1.0g USD 150.0 2 weeks
2.0g USD 250.0 2 weeks
5.0g USD 450.0 2 weeks
10.0g USD 650.0 2 weeks
20.0g USD 950.0 2 weeks
Bulk inquiry

Synonym: Bifonazole; Mycospor; Amycor; Bifonazol; Trifonazole; Bay H 4502; Bay H-4502; Bifokey; Bifomyk; Bifon; Canesten brand of bifonazole; Moldina

IUPAC/Chemical Name: 1-[Phenyl-(4-phenylphenyl)methyl]imidazole

InChi Key: OCAPBUJLXMYKEJ-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: C1=CC=CC(=C1)C(C2=CC=C(C=C2)C3=CC=CC=C3)N4C=NC=C4

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 310.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Piraccini BM, Bruni F, Alessandrini A, Starace M. Evaluation of efficacy and
tolerability of 4 weeks Bifonazole treatment after nail ablation with 40% urea in
mild to moderate distal subugnual onychomycosis. G Ital Dermatol Venereol. 2015
Oct 16. [Epub ahead of print] PubMed PMID: 26472342.

2: Chen Z, Liu Z, Qian F. Crystallization of bifonazole and acetaminophen within
the matrix of semicrystalline, PEO-PPO-PEO triblock copolymers. Mol Pharm. 2015
Feb 2;12(2):590-9. doi: 10.1021/mp500661v. Epub 2015 Jan 21. PubMed PMID:
25569586.

3: Cheng JS, Chou CT, Liang WZ, Kuo CC, Shieh P, Kuo DH, Jan CR. The mechanism of
bifonazole-induced [Ca(2+)]i rises and non-Ca(2+)-triggered cell death in PC3
human prostate cancer cells. J Recept Signal Transduct Res. 2014 Dec;34(6):493-9.
doi: 10.3109/10799893.2014.921201. Epub 2014 May 22. PubMed PMID: 24849495.

4: Tietz HJ, Hay R, Querner S, Delcker A, Kurka P, Merk HF. Efficacy of 4 weeks
topical bifonazole treatment for onychomycosis after nail ablation with 40% urea:
a double-blind, randomized, placebo-controlled multicenter study. Mycoses. 2013
Jul;56(4):414-21. doi: 10.1111/myc.12037. Epub 2013 Apr 16. PubMed PMID:
23586591.

5: Lahfa M, Bulai-Livideanu C, Baran R, Ortonne JP, Richert B, Tosti A, Piraccini
BM, Szepietowski JC, Sibaud V, Coubetergues H, Voisard JJ, Paul C. Efficacy,
safety and tolerability of an optimized avulsion technique with onyster® (40%
urea ointment with plastic dressing) ointment compared to bifonazole-urea
ointment for removal of the clinically infected nail in toenail onychomycosis: a
randomized evaluator-blinded controlled study. Dermatology. 2013;226(1):5-12.
doi: 10.1159/000345105. Epub 2013 Mar 1. PubMed PMID: 23467055.

6: Abdul Bari MA. Comparison of superficial mycosis treatment using Butenafine
and Bifonazole nitrate clinical efficacy. Glob J Health Sci. 2012 Nov
11;5(1):150-4. doi: 10.5539/gjhs.v5n1p150. PubMed PMID: 23283047.

7: Patel D, Patel D, Prajapati J, Patel U, Patel V. Formulation of
thermoresponsive and buccal adhesive in situ gel for treatment of oral thrush
containing poorly water soluble drug bifonazole. J Pharm Bioallied Sci. 2012
Mar;4(Suppl 1):S116-7. doi: 10.4103/0975-7406.94163. PubMed PMID: 23066185;
PubMed Central PMCID: PMC3467845.

8: Wächtler B, Wilson D, Hube B. Candida albicans adhesion to and invasion and
damage of vaginal epithelial cells: stage-specific inhibition by clotrimazole and
bifonazole. Antimicrob Agents Chemother. 2011 Sep;55(9):4436-9. doi:
10.1128/AAC.00144-11. Epub 2011 Jul 11. PubMed PMID: 21746947; PubMed Central
PMCID: PMC3165311.

9: El Hage S, Lajoie B, Feuillolay C, Roques C, Baziard G. Synthesis,
antibacterial and antifungal activities of bifonazole derivatives. Arch Pharm
(Weinheim). 2011 Jun;344(6):402-10. doi: 10.1002/ardp.201000304. Epub 2011 Mar
24. PubMed PMID: 21433056.

10: Billen F, Guieu LV, Bernaerts F, Mercier E, Lavoué R, Tual C, Peeters D,
Clercx C. Efficacy of intrasinusal administration of bifonazole cream alone or in
combination with enilconazole irrigation in canine sino-nasal aspergillosis: 17
cases. Can Vet J. 2010 Feb;51(2):164-8. PubMed PMID: 20436862; PubMed Central
PMCID: PMC2808281.

11: Van Eerdenbrugh B, Fanwick PE, Taylor LS.
1-[(Biphenyl-4-yl)(phen-yl)meth-yl]-1H-imidazole (bifonazole). Acta Crystallogr
Sect E Struct Rep Online. 2010 Sep 30;66(Pt 10):o2649. doi:
10.1107/S1600536810037876. PubMed PMID: 21587620; PubMed Central PMCID:
PMC2983152.

12: Linder N, Amarilla M, Hernandez A, Tamiri T, Sirota L, Klinger G, Levy I,
Merlob P. Association of high-dose bifonazole administration during early
pregnancy and severe limb reduction defects in the newborn. Birth Defects Res A
Clin Mol Teratol. 2010 Mar;88(3):201-4. doi: 10.1002/bdra.20644. PubMed PMID:
20014436.

13: Schaller M, Borelli C, Berger U, Walker B, Schmidt S, Weindl G, Jäckel A.
Susceptibility testing of amorolfine, bifonazole and ciclopiroxolamine against
Trichophyton rubrum in an in vitro model of dermatophyte nail infection. Med
Mycol. 2009 Nov;47(7):753-8. doi: 10.3109/13693780802577892. PubMed PMID:
19888808.

14: Mitsui H, Kanda N, Ohnishi T, Nakai K, Suzuki T, Watanabe S. [Usefulness of
bifonazole for treatment of tinea pedis in the 20th year after approval]. Jpn J
Antibiot. 2009 Apr;62(2):79-89. Japanese. PubMed PMID: 19673350.

15: Chourbagi C, Andrejak M, Gras V, Peltier M. [Muscle effects due to the
association of simvastatin and bifonazole cream]. Therapie. 2008
Nov-Dec;63(6):472-4. French. PubMed PMID: 19374035.

16: Toribio L, del Nozal MJ, Bernal JL, Alonso C, Jiménez JJ. Enantiomeric
resolution of bifonazole by supercritical fluid chromatography. J Sep Sci. 2006
Jul;29(10):1373-8. PubMed PMID: 16894781.

17: 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. Erratum in: Mycoses. 2006
Sep;49(5):441. PubMed PMID: 16681817.

18: Ferreyra CF, Ortiz CS. Simultaneous determination of bifonazole and tinctures
of calendula flower in pharmaceutical creams by reversed-phase liquid
chromatography. J AOAC Int. 2005 Nov-Dec;88(6):1649-54. PubMed PMID: 16526446.

19: Zhao Y, White MA, Muralidhara BK, Sun L, Halpert JR, Stout CD. Structure of
microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole:
insight into P450 conformational plasticity and membrane interaction. J Biol
Chem. 2006 Mar 3;281(9):5973-81. Epub 2005 Dec 21. PubMed PMID: 16373351.

20: Rupp B, Raub S, Marian C, Höltje HD. Molecular design of two sterol
14alpha-demethylase homology models and their interactions with the azole
antifungals ketoconazole and bifonazole. J Comput Aided Mol Des. 2005
Mar;19(3):149-63. PubMed PMID: 16059669.