Chlorphenesin carbamate

Names

[ CAS No. ]:
886-74-8

[ Name ]:
Chlorphenesin carbamate

[Synonym ]:
Carbamic Acid 3-(p-Chlorophenoxy)-2-hydroxypropyl Ester
3-[(4-chlorophenyl)oxy]-2-hydroxypropyl carbamate
MFCD00072002
3-(4-Chlorophenoxy)-2-hydroxypropyl carbamate
Chlorphensin carbamate
1,2-Propanediol, 3-(4-chlorophenoxy)-, 1-carbamate
Maolate
Kolpicortin-sine
[3-(4-chlorophenoxy)-2-hydroxypropyl] carbamate
1,2-Propanediol-3-(p-chlorophenoxy)-1-carbamate
Rinlaxer
Chlorphenesin
Chlorphenesin carbamate
EINECS 212-954-7

Biological Activity

[Description]:

Chlorphenesin carbamate is a centrally acting skeletal muscle relaxant. Chlorphenesin carbamate can be used for the research of pain and discomfort related to skeletal muscle trauma and inflammation[1]. Chlorphenesin carbamate is a selective blocker of polysynaptic pathways at the spinal and supra-spinal levels[2]. Antinociceptive effect[3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vivo]

Chlorphenesin carbamate (CPC; 50 mg/kg i.v.) inhibits the mono (MSR) and poly-synaptic reflex (PSR), the latter being more susceptible than the former to CPC depression. Chlorphenesin carbamate has an apparent depressant action on the spinal neuron, and it hyperpolarized both the ventral and dorsal roots of the isolated frog spinal cord[2]. Chlorphenesin carbamate (CPC) has an antinociceptive action in adjuvant arthritic rats. Chlorphenesin carbamate (100-400 mg/kg, p.o.) has a dose-dependent antinociceptive effect in the behavioral study. Chlorphenesin carbamate (25-50 mg/kg, i.v.) depresses the evoked neuronal responses of nociceptive neurons in the ventrobasal thalamus (VB) in the electrophysiological study. Chlorphenesin carbamate (50 mg/kg, i.v.) depresses the spontaneous firings of the VB nociceptive neurons[3]. Animal Model: Male Wister rats weighing 200-300 g[3] Dosage: 50 mg/kg Administration: Intravenously administered Result: Significantly inhibited PSR, with the maximum inhibition at 40 min after the drug administration.

[References]

[1]. Ji-young Yu, et al. Relative bioavailability of generic and branded 250-mg and 500-mg oral chlorphenesin carbamate tablets in healthy Korean volunteers: a single-dose, randomized-sequence, open-label, two-period crossover trial. Clin Ther. 2009 Nov;31(11):2735-43.

[2]. M Kurachi, et al. Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats. Jpn J Pharmacol. 1984 Sep;36(1):7-13.

[3]. S Okuyama, et al. Antinociceptive effect of chlorphenesin carbamate in adjuvant arthritic rats. Res Commun Chem Pathol Pharmacol. 1987 Feb;55(2):147-60.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
481.8±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₂ClNO₄

[ Molecular Weight ]:
245.660

[ Flash Point ]:
245.2±27.3 °C

[ Exact Mass ]:
245.045486

[ PSA ]:
81.78000

[ LogP ]:
1.41

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.564

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EZ2975000

CHEMICAL NAME :: Carbamic acid, 3-(p-chlorophenoxy)-2-hydroxypropyl ester

CAS REGISTRY NUMBER :: 886-74-8

LAST UPDATED :: 199806

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C10-H12-Cl-N-O4

MOLECULAR WEIGHT :: 245.68

WISWESSER LINE NOTATION :: ZVO1YQ1OR DG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 23 mg/kg/D

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - hallucinations, distorted perceptions Behavioral - muscle weakness

REFERENCE :: 34ZIAG "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969 Volume(issue)/page/year: -,171,1969

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 744 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) 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: 13,659,1977

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 354 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,386,1972

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 952 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Behavioral - ataxia 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: 13,659,1977

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 236 mg/kg

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

REFERENCE :: YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 21,1163,1979

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 807 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - changes in motor activity (specific assay) 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: 13,659,1977

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 475 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - changes in motor activity (specific assay) 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: 13,659,1977

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 923 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,437,1995

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 239 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,386,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 800 mg/kg

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

REFERENCE :: FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 27,870,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9900 mg/kg/30D-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 13,659,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60060 mg/kg/26W-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Cardiac - other changes

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 31,363,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 40 gm/kg/14W-I

TOXIC EFFECTS :: Liver - fatty liver degeneration Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 14,27,1977 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2800 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 31,363,1980