Bifonazole

Modify Date: 2024-01-02 18:14:00

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	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].

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

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	Signaling Pathways >> Anti-infection >> Fungal Research Areas >> Infection
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.

Description

Related Catalog

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

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.

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

Bifonazole MSDS(Chinese)

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

Symbol	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

N/A

CAS#:162824-42-2

~95%

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Precursor 4
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DownStream 0

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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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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