Basic information
- CAS
60628-96-8- Standard SMILES
c1ccc(-c2ccc(C(c3ccccc3)n3ccnc3)cc2)cc1- InChIKey
OCAPBUJLXMYKEJ-UHFFFAOYSA-N- Molecular formula
- C22H18N2
- Average molar mass
- 310.4 g/mol
- Monoisotopic mass
- 310.14699858
Names & identifiers
- Preferred name
- Bifonazole
- IUPAC
- 1-[phenyl-(4-phenylphenyl)methyl]imidazole
- English name
- Bifonazole
- Molecular formula
- C22H18N2
- Molecular weight
- 310.39
Names & synonyms
bifonazole60628-96-8MycosporTrifonazoleBifonazolBAY H 4502BifonazolumBay H-45021-((4-Biphenylyl)phenylmethyl)-1H-imidazole1-(alpha-(4-Biphenylyl)benzyl)imidazoleBay-h-4502(+-)-1-(p,alpha-Diphenylbenzyl)imidazole
Show more names
Bifonazole API1[4,ALPHA-DIPHENYLBENZYL]-IMIDAZOLE1-[phenyl-(4-phenylphenyl)-methyl]imidazole1-([1,1'-Biphenyl]-4-yl(phenyl)methyl)-1H-imidazoleAmycorBedridA-One-LAzolmen
DTXSID9045631NSC-758954QYJ305Z91OD01AC10DTXCID70256311-((4-biphenylyl)-phenylmethyl)-1H-imidazole1H-Imidazole, 1-((1,1'-biphenyl)-4-ylphenylmethyl)-, (+-)-1-(phenyl(4-phenylphenyl)methyl)-1H-imidazole
Database identifiers
- CAS
60628-96-8- PubChem CID
- 2378
- DTXSID
DTXSID9045631- ChEMBL
CHEMBL277535- ChEBI
CHEBI:78692- UNII
- QYJ305Z91O
- EC Number
- 262-336-6
- Nikkaji
- J17.988D
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 17.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 362
Experimental & physicochemical properties
LogP
4.77
4.77
Solubility
2.45e-03 g/L
0.7 [ug/mL] (The mean of the results at pH 7.4)
Melting Point142
Physical DescriptionSolid
Collision Cross Section
184.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
171.48 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；177.23 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 142 ℃ · 142℃
- Boiling point
- 440.55 °C · 440.55°C (rough estimate)
- Density
- 1.115 · 1.1150 (rough estimate)
- refractive index
- 1.762 · 1.7620 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in DMSO
- form
- powder
- pka
- 6.55 · 6.55±0.22(Predicted)
- color
- white to off-white
- Merck
- 14 · 14,1213
- Cosmetics Ingredients Functions
- ANTI-SEBORRHEICANTIMICROBIAL
- 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
- SMILES
- C(C1C=CC=CC=1)(N1C=NC=C1)C1C=CC(C2C=CC=CC=2)=CC=1
- LogP
- 4.77 · 4.770
- CAS DataBase Reference
- 60628 · 60628-96-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 305 Z91O · QYJ305Z91O
- ATC code
- 1 AC10,D01AC60 · D01AC10,D01AC60
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- WGK Germany
- 1 · 1
- RTECS
- 3517000 · NI3517000
- HS Code
- 29332900 · 29332900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 in · LD50 in male mice, rats (mg/kg): 2629, 2854 orally (Schlüter)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 72 reports by companies from 4 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 1
- rtecs
- NI3517000
- hs_code
- 29332900
- Toxicity
- LD50 in male mice, rats (mg/kg): 2629, 2854 orally (Schlüter)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
ATC Code
D01AC10
D - Dermatologicals；D01 - Antifungals for dermatological use；D01A - Antifungals for topical use；D01AC - Imidazole and triazole derivatives；D01AC10 - Bifonazole
QD - Dermatologicals；QD01 - Antifungals for dermatological use；QD01A - Antifungals for topical use；QD01AC - Imidazole and triazole derivatives；QD01AC10 - Bifonazole
PharmacodynamicsBifonazole is a type of antifungal medicine known as an imidazole. It kills fungi and yeasts by interfering with their cell membranes.
Mechanism of Action
Bifonazole works by inhibiting the production of a substance called ergosterol, which is an essential component of fungal cell membranes.It acts to destabilize the fungal cyctochrome p450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. The disruption in production of ergosterol disrupts the cell membrane and causes holes to appear. The cell membranes of fungi are vital for their survival. They keep unwanted substances from entering the cells and stop the contents of the cells from leaking out. As bifonazole causes holes to appear in the cell membranes, essential constituents of the fungal cells can leak out. This kills the fungi.
Biological Half-Life1-2 hours
Metabolism/MetabolitesHepatic.
MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Absorption, Distribution and ExcretionVery low absorption following topical administration (0.6% of an applied dose). In cases of skin lesions absorption is increased (2.5%).
Cellular LocationsMembrane
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >250；Consumption (g per capita; approx.) in Germany (2009): 0.00305；Calculated removal (%): 92.3
Applications
DescriptionBifonazole 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.
DescriptionBifonazole 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.
UsesBifonazole 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.
Usesantibacterial
Upstream & downstream products
Upstream raw materials
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉灵灵九生物科技有限公司15623309010
T&W GROUP021-61551611 13296011611 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
武汉泽诺生物科技有限公司027-87781970 15172508891 · [email protected]
杭州东帆化学有限公司86-0571-85151182
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TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
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广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
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天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
中山万汉制药有限公司4008930086 13823019268 · [email protected]
斯派螺（武汉）药物研发有限公司[email protected]
成都瑞欧克科技有限公司028-64353063 · [email protected]
九鼎化学（上海）科技有限公司4009209199 · [email protected]
Ring Specialty Chemicals Inc.+1 416 493 6870 · [email protected]
杭州鼎燕化工有限公司0571-87157530-8003 18267553885 · [email protected]
泰州东邦精细化工有限公司0523-86235448 15996000437 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
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上海前衍生物科技有限公司02781293128 · [email protected]
Additional notes
DefinitionChEBI: 1-[biphenyl-4-yl(phenyl)methyl]imidazole is a member of the class of imidazoles carrying an alpha-(biphenyl-4-yl)benzyl substituent at position 1. It is a member of imidazoles and a member of biphenyls.
Related reactions
14 records
Compound notes
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