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Chlorzoxazone

Catalog No. DB00356 Name DrugBank
CAS Number 95-25-0 Website http://www.ualberta.ca/
M. F. C7H4ClNO2 Telephone (780) 492-3111
M. W. 169.56516 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 240

SYNONYMS

IUPAC name
5-chloro-2,3-dihydro-1,3-benzoxazol-2-one
IUPAC Traditional name
chlorzoxazone
Brand Name
Solaxin
Remular
Myoflexine
Parafon Forte Dsc
Paraflex
Relaxazone
Biomioran
EZE-DS
Escoflex
Neoflex
Remular-S
Usaf Ma-10
Flexazone
Mioran
Miotran
Myoflexin
Pathorysin
Strifon Forte Dsc
Synonyms
Chloroxazone
Chlorzoxazon
Chlorzoxane

DATABASE IDS

PubChem CID 2733
CAS Number 95-25-0
PubChem SID 46507755

PROPERTIES

Hydrophobicity(logP) 1.6
Solubility 1000 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202)
Indication For the relief of discomfort associated with acute painful musculoskeletal conditions.
Pharmacology Chlorzoxazone, a synthetic compound, inhibits antigen-induced bronchospasms and, hence, is used to treat asthma and allergic rhinitis. Chlorzoxazone is used as an ophthalmic solution to treat conjunctivitis and is taken orally to treat systemic mastocytosis and ulcerative colitis. Chlorzoxazone is also a centrally-acting agent for painful musculoskeletal conditions. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex a.c. involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles.
Toxicity Oral, mouse: LD50 = 440 mg/kg; Oral, rat: LD50 = 763 mg/kg; Symptoms of overdose include diarrhea, dizziness, drowsiness, headache, light-headedness, nausea, and vomiting.
Affected Organisms
Humans and other mammals
Biotransformation Chlorzoxazone is rapidly metabolized in the liver and is excreted in the urine, primarily in a conjugated form as the glucuronide.
Protein Binding 13-18%
Elimination Chlorzoxazone is rapidly metabolized and is excreted in the urine, primarily in a conjugated form as the glucuronide.
References
Dong DL, Luan Y, Feng TM, Fan CL, Yue P, Sun ZJ, Gu RM, Yang BF: Chlorzoxazone inhibits contraction of rat thoracic aorta. Eur J Pharmacol. 2006 Sep 18;545(2-3):161-6. Epub 2006 Jun 29. [Pubmed]
Park JY, Kim KA, Park PW, Ha JM: Effect of high-dose aspirin on CYP2E1 activity in healthy subjects measured using chlorzoxazone as a probe. J Clin Pharmacol. 2006 Jan;46(1):109-14. [Pubmed]
Wan J, Ernstgard L, Song BJ, Shoaf SE: Chlorzoxazone metabolism is increased in fasted Sprague-Dawley rats. J Pharm Pharmacol. 2006 Jan;58(1):51-61. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
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REFERENCES

  • Dong DL, Luan Y, Feng TM, Fan CL, Yue P, Sun ZJ, Gu RM, Yang BF: Chlorzoxazone inhibits contraction of rat thoracic aorta. Eur J Pharmacol. 2006 Sep 18;545(2-3):161-6. Epub 2006 Jun 29. Pubmed
  • Park JY, Kim KA, Park PW, Ha JM: Effect of high-dose aspirin on CYP2E1 activity in healthy subjects measured using chlorzoxazone as a probe. J Clin Pharmacol. 2006 Jan;46(1):109-14. Pubmed
  • Wan J, Ernstgard L, Song BJ, Shoaf SE: Chlorzoxazone metabolism is increased in fasted Sprague-Dawley rats. J Pharm Pharmacol. 2006 Jan;58(1):51-61. Pubmed