Bifonazole

Base Information

• Chemical Name: Bifonazole
• CAS No.: 60628-96-8
• Molecular Formula: C22H18N2
• Molecular Weight: 310.398
• Hs Code.: 29332900
• European Community (EC) Number: 262-336-6
• NSC Number: 758954
• UNII: QYJ305Z91O
• DSSTox Substance ID: DTXSID9045631
• Nikkaji Number: J17.988D
• Wikipedia: Bifonazole
• Wikidata: Q421162
• NCI Thesaurus Code: C87450
• Pharos Ligand ID: 5S5WULBAQTUJ
• Metabolomics Workbench ID: 43624
• ChEMBL ID: CHEMBL277535
• Mol file: 60628-96-8.mol

Synonyms:1-((4-biphenylyl)-phenylmethyl)-1H-imidazole;Amycor;Bay H 4502;Bay H-4502;Bifokey;Bifomyk;Bifon;bifonazole;Moldina;Mycospor

Chemical Property of Bifonazole

Chemical Property:

• Vapor Pressure: 2.46E-09mmHg at 25°C
• Melting Point: 142℃
• Refractive Index: 1.616
• Boiling Point: 491.728 °C at 760 mmHg
• PKA: 6.55±0.22(Predicted)
• Flash Point: 251.188 °C
• PSA: 17.82000
• Density: 1.077 g/cm³
• LogP: 5.18780
• Storage Temp.: room temp
• Solubility.: Soluble in DMSO
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 310.146998583
• Heavy Atom Count: 24
• Complexity: 362

Purity/Quality:

99% ^*data from raw suppliers

(±)-Bifonazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)C(C3=CC=CC=C3)N4C=CN=C4
• Recent ClinicalTrials: Treatment of Onychomycosis With Loceryl (Amorolfine) Nail Lacquer 5% Versus a Two-course Treatment With Urea 40% Ointment and Bifonazole Cream 1%
• Recent EU Clinical Trials: An investigator-blind, randomized, multicenter, 5-arm, placebo- and active controlled parallel group pilot trial to explore the efficacy and tolerability of topical bifonazole liquid spray in patients with athlete’s foot
• Description: Bifonazole represents the first topical broad spectrum antimycotic approved for once daily administration. Its in vitro activity appears equivalent to its structural relative clotrimazole, being effective against dermatophytes, other filamentous fungi, dimorphic fungi and yeasts. Bifonazole is a topically-active imidazole antifungal compound that has broad spectrum activity in vitro against dermatophytes, molds, yeasts, dimorphic fungi, and some Gram-positive bacteria. It is effective in the treatment of experimental dermatophytic and Candida in animals. Bifonazole is also a potent inhibitor of cytochrome P450 aromatase (Ki = 68 nM, IC50 = 270 nM), which catalyzes the biosynthesis of estrogens from androgens. When applied topically in animals, it demonstrates prolonged retention time in skin with minimal percutaneous absorption, thus minimizing its effect on aromatase.
• Uses: Bifonazole is an imidazole antifungal agent and calmodulin antagonist. It causes a reduction in glycolysis and ATP levels in B16 melanoma cells. Bifonazole is an inhibitor of C14orf1. 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. antibacterial
• Therapeutic Function: Antifungal

Technology Process of Bifonazole

There total 26 articles about Bifonazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(R,S)-1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarboxylic acid (162824-42-2) → bifonazole (60628-96-8,91487-86-4)

Guidance literature:

In diphenylether; for 0.5h; Heating;

DOI:10.1021/jo00112a023

Reference yield: 77.0%

1H-imidazole (288-32-4) + 4-benzylbiphenyl (613-42-3) → bifonazole (60628-96-8,91487-86-4)

Guidance literature:

4-benzylbiphenyl; With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 0.833333h; Inert atmosphere; Reflux;

1H-imidazole; With potassium carbonate; In acetonitrile; for 1h; Reflux;

Reference yield: 52.0%

1H-imidazole (288-32-4) + C26H21N2O2S(1-)*Na(1+) → bifonazole (60628-96-8,91487-86-4)

Guidance literature:

With copper acetylacetonate; tetrabutylammomium bromide; In toluene; at 85 ℃; for 36h;

DOI:10.1016/j.tet.2004.08.009

upstream raw materials:

(R,S)-1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarboxylic acid

1H-imidazole

4-phenylbenzhydrol

1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile

Downstream raw materials:

1-[α-(4-biphenylyl)-benzyl]-3-benzoylmethyl-imidazolium bromide

Refernces

• 1、 Chen, Xiao-Yue,Nie, Xiao-Xue,Wu, Yichen,Wang, Peng. "para-Selective arylation and alkenylation of monosubstituted arenes using thianthreneS-oxide as a transient mediator". . p. 5058 - 5061. Retrieved 2020/05/18.
• 2、 Xia, Ji-Bao,Zhang, Zheng-Bing. "NHC-Nickel Catalyzed C-N Bond Cleavage of Mono-protected Anilines for C-C Cross-Coupling". supporting information. p. 9609 - 9613. Retrieved 2020/12/21.