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Substance Name: Chlormezanone [INN:BAN:JAN]
RN: 80-77-3
UNII: GP568V9G19
InChIKey: WEQAYVWKMWHEJO-UHFFFAOYSA-N

Note

  • A non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm.

Molecular Formula

  • C11-H12-Cl-N-O3-S

Molecular Weight

  • 273.7388
 

Classification Codes

  • Anti-Anxiety Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Muscle Relaxants, Central
  • Neuromuscular Agents
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Tranquilizing Agents
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Names and Synonyms

Name of Substance

  • Chlormezanone
  • Chlormezanone [INN:BAN:JAN]

MeSH Heading

  • Chlormezanone

Synonyms

  • (+-)-Chlormezanone
  • (+-)-Fenarol
  • 2-(4-Chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide
  • 2-(4-Chlorphenyl)-3-methyl-4-metathiazanon-1,1-dioxid
  • 2-(p-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide
  • 2-(p-Chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide
  • 2-(para-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one, 1,1-dioxide
  • 4H-1,3-Thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-1,1-dioxide
  • 4H-1,3-Thiazin-4-one, 2-(p-chlorophenyl)tetrahydro-3-methyl-1,1-dioxide
  • 4H-1,3-Thiazin-4-one, tetrahydro-2-(p-chlorophenyl)-3-methyl-, 1,1-dioxide
  • Alinam
  • Banabil-sintyal
  • Banabin
  • Banabin-sintyal
  • Bisina
  • Chlormethazanone
  • Chlormethazone
  • Chlormezanon
  • Chlormezanone
  • Chlormezanonum
  • Chlormezanonum [INN-Latin]
  • Clorilax
  • Clormetazanone
  • Clormetazon
  • Clormezanona
  • Clormezanona [INN-Spanish]
  • Clormezanone
  • Clormezanone [DCIT]
  • dl-Chlormezanone
  • EINECS 201-307-4
  • Fenarol
  • HSDB 3300
  • Mio-sed
  • Miorilax
  • Muskel-trancopal
  • Myolespen
  • NSC 169108
  • Phenarol
  • Rexan
  • Rilansyl
  • Rilaquil
  • Rilassol
  • Rilax
  • Supotran
  • Tanafol
  • Trancopal
  • Trancote
  • Tranrilax
  • UNII-GP568V9G19
  • WIN 4692

Systematic Names

  • 2-(p-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide
  • 4H-1,3-Thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide
  • Chlormezanone

Registry Numbers

CAS Registry Number

  • 80-77-3

FDA UNII

  • GP568V9G19

Other Registry Number

  • 102818-65-5

System Generated Number

  • 0000080773

Structure Descriptors

InChI

1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3

InChIKey

WEQAYVWKMWHEJO-UHFFFAOYSA-N

Smiles

C1(c2ccc(cc2)Cl)S(=O)(=O)CCC(=O)N1C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral > 400mg/kg (400mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 168, 1959.
dog LD50 oral 500mg/kg (500mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 168, 1959.
guinea pig LD50 intraperitoneal 600mg/kg (600mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 168, 1959.
man TDLo oral 157mg/kg (157mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: ATAXIA

BEHAVIORAL: COMA
British Medical Journal. Vol. 292, Pg. 732, 1986.
mouse LD50 intraperitoneal 514mg/kg (514mg/kg)   Anesthesie, Analgesie, Reanimation. Vol. 19, Pg. 603, 1962.
mouse LD50 oral 600mg/kg (600mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 9, Pg. 601, 1975.
mouse LD50 subcutaneous 322mg/kg (322mg/kg) BEHAVIORAL: ANTICONVULSANT Acta Pharmacologica et Toxicologica. Vol. 19, Pg. 247, 1962.
rat LD50 intraperitoneal 370mg/kg (370mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 242, 1967.
rat LD50 oral 605mg/kg (605mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ANTIPSYCHOTIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 280, 1961.
women LDLo oral 20gm/kg (20000mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: EMPHYSEMA
Hochudoku. Vol. 9, Pg. 168, 1991.
women TDLo oral 140mg/kg (140mg/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
British Medical Journal. Vol. 286, Pg. 845, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 116.2 deg C   EXP
log P (octanol-water) -0.260 (none)   EST
Water Solubility 2500 mg/L 25 EXP
Atmospheric OH Rate Constant 1.09E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.