Clotrimazole

Modify Date: 2024-01-02 18:31:59

Clotrimazole structure	Common Name	Clotrimazole
	CAS Number	23593-75-1	Molecular Weight	344.837
	Density	1.1±0.1 g/cm3	Boiling Point	482.3±40.0 °C at 760 mmHg
	Molecular Formula	C₂₂H₁₇ClN₂	Melting Point	147-149ºC
	MSDS	Chinese USA	Flash Point	245.5±27.3 °C
	Symbol	GHS07	Signal Word	Warning

Use of Clotrimazole

Clotrimazole is an imidazole derivative, an antifungal compound and is a CYP (cytochrome P450) inhibitor.Target: Antifungal; CYPClotrimazole (brand name Canesten or Lotrimin) is an antifungal medication commonly used in the treatment of fungal infections (of both humans and other animals) such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and jock itch.It is commonly available as an over-the-counter substance in various dosage forms, such as a cream, and also (especially in the case of ear infection) as a combination medicine. It is also available as a troche or throat lozenge (prescription only). For ear infection, it is often applied in liquid form, as ear drops.The antimycotic drug clotrimazole inhibits the function of the gastric H,K-ATPase in a manner similar to that observed for the Na,K-ATPase. Because of the high hydrophobicity of the compound, the interaction between clotrimazole and the ion pump occurs at the membrane domain in the apolar core of the membrane. The enzymatic activity was inhibited with a half-saturating concentration of 5.2 microM. Various partial reactions of the pump cycle were analyzed with the electrochromic styryl dye RH421 that has been widely used to study the transport mechanism of P-type ATPases.

Name	clotrimazole
Synonym	More Synonyms

Description	Clotrimazole is an imidazole derivative, an antifungal compound and is a CYP (cytochrome P450) inhibitor.Target: Antifungal; CYPClotrimazole (brand name Canesten or Lotrimin) is an antifungal medication commonly used in the treatment of fungal infections (of both humans and other animals) such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and jock itch.It is commonly available as an over-the-counter substance in various dosage forms, such as a cream, and also (especially in the case of ear infection) as a combination medicine. It is also available as a troche or throat lozenge (prescription only). For ear infection, it is often applied in liquid form, as ear drops.The antimycotic drug clotrimazole inhibits the function of the gastric H,K-ATPase in a manner similar to that observed for the Na,K-ATPase. Because of the high hydrophobicity of the compound, the interaction between clotrimazole and the ion pump occurs at the membrane domain in the apolar core of the membrane. The enzymatic activity was inhibited with a half-saturating concentration of 5.2 microM. Various partial reactions of the pump cycle were analyzed with the electrochromic styryl dye RH421 that has been widely used to study the transport mechanism of P-type ATPases.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Anti-infection >> Fungal Research Areas >> Infection
References	[1]. Sawyer PR, Clotrimazole: a review of its antifungal activity and therapeutic efficacy. Drugs. 1975;9(6):424-47. [2]. Witzke A, Inhibition of the gastric H,K-ATPase by clotrimazole. Biochemistry. 2010 Jun 1;49(21):4524-32.

Description

Related Catalog

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

References

[1]. Sawyer PR, Clotrimazole: a review of its antifungal activity and therapeutic efficacy. Drugs. 1975;9(6):424-47.

[2]. Witzke A, Inhibition of the gastric H,K-ATPase by clotrimazole. Biochemistry. 2010 Jun 1;49(21):4524-32.

Density	1.1±0.1 g/cm3
Boiling Point	482.3±40.0 °C at 760 mmHg
Melting Point	147-149ºC
Molecular Formula	C₂₂H₁₇ClN₂
Molecular Weight	344.837
Flash Point	245.5±27.3 °C
Exact Mass	344.108032
PSA	17.82000
LogP	5.44
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.617
Storage condition	Store at RT.
Water Solubility	Soluble in chloroform, DMSO, DMF and alcohols

Clotrimazole MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI4377000

CHEMICAL NAME :: Imidazole, 1-(o-chloro-alpha,alpha-diphenylbenzyl)-

CAS REGISTRY NUMBER :: 23593-75-1

BEILSTEIN REFERENCE NO. :: 0622318

LAST UPDATED :: 199612

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C22-H17-Cl-N2

MOLECULAR WEIGHT :: 344.86

WISWESSER LINE NOTATION :: T5N CNJ AXR&R&R BG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 28 mg/kg/7D

TOXIC EFFECTS :: Skin and Appendages - primary irritation (after topical exposure)

REFERENCE :: CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 18,41,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 708 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: 22,1272,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 445 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,1333,1973

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,1333,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 761 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: 22,1272,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 108 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 13,195,1990

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,1333,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1272,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1272,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1272,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AACHAX Antimicrobial Agents and Chemotherapy (1961-70). (Ann Arbor, MI) 1961-70. For publisher information, see AMACCQ. Volume(issue)/page/year: -,271,1969 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7 gm/kg/5W-C

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Blood - normocytic anemia

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,1340,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 mg/kg/26W-C

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Blood - normocytic anemia

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,1340,1973 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 600 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,359,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2750 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 18,4937,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 4200 mg/kg

SEX/DURATION :: male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 18,4917,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 6500 mg/kg

SEX/DURATION :: female 17-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 18,4981,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1400 mg/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,359,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 7 gm/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,359,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 600 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 7,359,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5350 No. of Facilities: 421 (estimated) No. of Industries: 3 No. of Occupations: 3 No. of Employees: 9288 (estimated) No. of Female Employees: 7550 (estimated)

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn: Harmful;
Risk Phrases	R22
Safety Phrases	26-36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	NI4377000
HS Code	2933290012

Precursor 5
CAS#:288-32-4 Imidazole CAS#:102-10-3 diphenyl phosphite CAS#:66774-02-5 MDK-4025 CAS#:108-10-1 4-Methyl-2-pentanone
CAS#:42074-68-0 2-Chlorotrityl ...
DownStream 1
CAS#:66774-02-5 MDK-4025

HS Code	2933290012
Summary	2933290012 1-((2-chlorophenyl)diphenylmethyl)-1h-imidazole。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%

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1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole

Gyne-Lotrimin

Empecid

Rimazole

1-[(2-chlorophenyl)-diphenylmethyl]imidazole

1-(o-Chlorotrityl)imidazole,1-(o-Chl

Trimysten

1-[(o-Chlorophenyl)diphenylmethyl]imidazole

Tibatin

1H-Imidazole, 1-[(2-chlorophenyl)diphenylmethyl]-

1-(2-Chlorotrityl)imidazole

1H-Imidazole, 1-[(2-chlorophenyl)-diphenylmethyl]

Canifug

Canesten

Mycelex G

Imidazole, 1- (o-chloro-α,α-diphenylbenzyl)-

1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole (9CI)

Mycelex

1-(o-Chlorotrityl)imidazole

Mycosporin

1-[a-(2-Chlorophenyl)benzhydryl]imidazole

Pedisafe

Mono-baycuten

1-[(2-Chlorophenyl)diphenylmethyl]imidazole

1-(o-Chloro-a,a-diphenylbenzyl)imidazole

Fungicip

MFCD00057220

UNII-G07GZ97H65

EINECS 245-764-8

1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole

Lotrimin

Clotrimazole

Clotrimazole crystalline

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Clotrimazole

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