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MedKoo Cat#: 317325 | Name: Bifonazole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Bifonazole
Bifonazole
CAS#60628-96-8

Theoretical Analysis

MedKoo Cat#: 317325

Name: Bifonazole

CAS#: 60628-96-8

Chemical Formula: C22H18N2

Exact Mass: 310.1470

Molecular Weight: 310.39

Elemental Analysis: C, 85.13; H, 5.85; N, 9.03

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 Weeks
5g USD 550.00 2 Weeks
25g USD 1,250.00 2 Weeks
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Related CAS #
No Data
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
>97% (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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Bifonazole (Bay H-4502) is an imidazole antifungal drug.
In vitro activity:
Together, in PC3 human prostate cancer cells, bifonazole induced [Ca(2+)]i rises by inducing phospholipase C- and protein kinase C-dependent Ca(2+) release from the endoplasmic reticulum and Ca(2+) influx via non-store-operated pathways. Bifonazole induced cell death that might involve apoptosis. Reference: J Recept Signal Transduct Res. 2014 Dec;34(6):493-9. https://pubmed.ncbi.nlm.nih.gov/24849495/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 37.1 119.56
DMF 25.0 80.54
DMF:PBS (pH 7.2) (1:4) 0.2 0.64
Ethanol 15.0 48.33
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
Formulation protocol:
1. 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. PMID: 24849495. 2. Stel'mashuk EV, Andreeva NA, Manukhova L, Zorov DB, Isaev NK. Bifonazole modulates death of cultured cerebellar granular cells induced by glutamate and oxygen-glucose deprivation. Bull Exp Biol Med. 2001 Nov;132(5):1076-8. doi: 10.1023/a:1017920725582. PMID: 11865326.
In vitro protocol:
1. 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. PMID: 24849495. 2. Stel'mashuk EV, Andreeva NA, Manukhova L, Zorov DB, Isaev NK. Bifonazole modulates death of cultured cerebellar granular cells induced by glutamate and oxygen-glucose deprivation. Bull Exp Biol Med. 2001 Nov;132(5):1076-8. doi: 10.1023/a:1017920725582. PMID: 11865326.
In vivo protocol:
TBD
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.