Bifonazole

Modify Date: 2025-08-22 17:37:17

Bifonazole Structure
Bifonazole structure
 Common Name Bifonazole
CAS Number 60628-96-8 Molecular Weight 310.392
Density 1.1±0.1 g/cm3 Boiling Point 491.7±24.0 °C at 760 mmHg
Molecular Formula C22H18N2 Melting Point 142℃
MSDS Chinese USA Flash Point 251.2±22.9 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Bifonazole


Bifonazole is an imidazole antifungal drug.Target: AntifungalBifonazole, a new broad-spectrum antimycotic, interferes with sterol biosynthesis. In dermatophytes bifonazole additionally inhibits directly HMG-CoA-reductase. bifonazole possesses a sequential mode of action, namely inhibition of cytochrome P450-dependent C14-demethylation of sterols and direct inhibition of HMG-CoA-reductase. In vitro bifonazole shows a strongly pH-dependent efficacy. The uptake kinetics of bifonazole have been measured with different pathogens [1]. Bifonazole additionally leads to a generally decreased rate of sterol biosynthesis as compared to clotrimazole, due to a direct inhibition of microsomal HMG-CoA-reductase. The additional fungicidal effects of bifonazole are considered to originate from a sequential action by inhibition of HMG-CoA-reductase and of cytochrome P450 [2]. bifonazole were affected by choice of medium with Kimmig's agar generally giving the lowest MIC's. Bifonazole MICs were shown to vary with pH (maximal activity at pH 6 . 5) with selected yeasts when tested on Kimmig's agar [3].

 Names

Name 1-[phenyl-(4-phenylphenyl)methyl]imidazole
Synonym More Synonyms

 Bifonazole Biological Activity

Description Bifonazole is an imidazole antifungal drug.Target: AntifungalBifonazole, a new broad-spectrum antimycotic, interferes with sterol biosynthesis. In dermatophytes bifonazole additionally inhibits directly HMG-CoA-reductase. bifonazole possesses a sequential mode of action, namely inhibition of cytochrome P450-dependent C14-demethylation of sterols and direct inhibition of HMG-CoA-reductase. In vitro bifonazole shows a strongly pH-dependent efficacy. The uptake kinetics of bifonazole have been measured with different pathogens [1]. Bifonazole additionally leads to a generally decreased rate of sterol biosynthesis as compared to clotrimazole, due to a direct inhibition of microsomal HMG-CoA-reductase. The additional fungicidal effects of bifonazole are considered to originate from a sequential action by inhibition of HMG-CoA-reductase and of cytochrome P450 [2]. bifonazole were affected by choice of medium with Kimmig's agar generally giving the lowest MIC's. Bifonazole MICs were shown to vary with pH (maximal activity at pH 6 . 5) with selected yeasts when tested on Kimmig's agar [3].
Related Catalog
References

[1]. Berg, D. and M. Plempel, Bifonazole, a biochemist's view. Dermatologica, 1984. 169 Suppl 1: p. 3-9.

[2]. Berg, D., et al., Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung, 1984. 34(2): p. 139-46.

[3]. Shadomy, S., D.M. Dixon, and R. May, A comparison of bifonazole (BAY H 4502) with clotrimazole in vitro. Sabouraudia, 1982. 20(4): p. 313-23.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 491.7±24.0 °C at 760 mmHg
Melting Point 142℃
Molecular Formula C22H18N2
Molecular Weight 310.392
Flash Point 251.2±22.9 °C
Exact Mass 310.147003
PSA 17.82000
LogP 4.84
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.616

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NI3517000
CHEMICAL NAME :
Imidazole, 1-(alpha-(4-biphenylyl)benzyl)-
CAS REGISTRY NUMBER :
60628-96-8
BEILSTEIN REFERENCE NO. :
0618427
LAST UPDATED :
199612
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C22-H18-N2
MOLECULAR WEIGHT :
310.42
WISWESSER LINE NOTATION :
T5N CNJ AYR&R DR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1463 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Skin and Appendages - hair
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 28,23,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 28,23,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
63 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 28,23,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2629 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,739,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>15 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 28,23,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
57 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 28,23,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,739,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,739,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10500 mg/kg/5W-C
TOXIC EFFECTS :
Liver - other changes Blood - normocytic anemia Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 28,23,1984 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1160 mg/kg
SEX/DURATION :
female 16-22 day(s) after conception lactating female 22 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,739,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1200 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,739,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
390 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,739,1983

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Hazard Codes Xn
Risk Phrases 22
RIDADR NONH for all modes of transport
WGK Germany 1
RTECS NI3517000
HS Code 2933290090

 Synthetic Route

N/A structure

N/A

CAS#:162824-42-2

~95%

Bifonazole Structure

Bifonazole

CAS#:60628-96-8

Literature: Corelli; Summa; Brogi; Monteagudo; Botta Journal of Organic Chemistry, 1995 , vol. 60, # 7 p. 2008 - 2015
4-(chlorophenylmethyl)-1,1'-biphenyl structure

4-(chlorophenyl...

CAS#:7515-73-3

N-(Trimethylsilyl)imidazole structure

N-(Trimethylsil...

CAS#:18156-74-6

~%

Bifonazole Structure

Bifonazole

CAS#:60628-96-8

Literature: US4118487 A1, ;
phenyl-(4-phenylphenyl)methanol structure

phenyl-(4-pheny...

CAS#:7598-80-3

~%

Bifonazole Structure

Bifonazole

CAS#:60628-96-8

Literature: Journal of Organic Chemistry, , vol. 60, # 7 p. 2008 - 2015
1-(α-(4-Biphenylyl)benzyl)imidazole-4,5-dicarbonitrile structure

1-(α-(4-Bipheny...

CAS#:162824-36-4

~%

Bifonazole Structure

Bifonazole

CAS#:60628-96-8

Literature: Journal of Organic Chemistry, , vol. 60, # 7 p. 2008 - 2015
phenyl-(4-phenylphenyl)methanol structure

phenyl-(4-pheny...

CAS#:7598-80-3

N,N-Carbonyldiimidazole structure

N,N-Carbonyldii...

CAS#:530-62-1

~11%

Bifonazole Structure

Bifonazole

CAS#:60628-96-8

Literature: Hu, Qingzhong; Negri, Matthias; Jahn-Hoffmann, Kerstin; Zhuang, Yan; Olgen, Sureyya; Bartels, Marc; Mueller-Vieira, Ursula; Lauterbach, Thomas; Hartmann, Rolf W. Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 16 p. 7715 - 7727

 Customs

HS Code 2933290090
Summary 2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

Bifonazole
1-[PHENYL-(4-PHENYLPHENYL)-METHYL]IMIDAZOLE
rac-bifonazole
(±)-Bifonazole
(biphenyl-4-yl)phenyl-imidazol-1-ylmethane
1-[4-Biphenylyl(phenyl)methyl]-1H-imidazole
Canespor
1H-Imidazole, 1-([1,1'-biphenyl]-4-ylphenylmethyl)-
Bifonazol [INN-Spanish]
Azolmen
Trifonazole
EINECS 262-336-6
BAY H 4502
1-[biphenyl-4-yl(phenyl)methyl]imidazole
Amycor
1-[biphenyl-4-yl(phenyl)methyl]-1H-imidazole
1-[Biphenyl-4-yl(phenyl)methyl]-1H-imidazol
Bifazol
1-(biphenyl-4-yl-phenyl-methyl)-1H-imidazole
(±)-1-(p,a-Diphenylbenzyl)imidazole
1-([1,1'-Biphenyl]-4-ylphenylmethyl)-1H-imidazole
Bifonazol
Mycospor
Bifonazolum
MFCD00865567
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