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23593-75-1

23593-75-1 structure
23593-75-1 structure
  • Name: Clotrimazole
  • Chemical Name: clotrimazole
  • CAS Number: 23593-75-1
  • Molecular Formula: C22H17ClN2
  • Molecular Weight: 344.837
  • Catalog: API Synthetic anti-infective drugs Antifungal drugs
  • Create Date: 2018-02-04 08:00:00
  • Modify Date: 2024-01-02 18:31:59
  • 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
Synonyms 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
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
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

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
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
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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