Chlorzoxazone

Chlorzoxazone
Clinical data
Trade namesLorzone, Paraflex, Muscol
AHFS/Drugs.comMonograph
MedlinePlusa682577
License data
Routes of
administration		By mouth
Drug classSkeletal muscle relaxants
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityWell absorbed
Protein binding13–18%
MetabolismHepatic
Elimination half-life1.1 hours
Duration of action3–4 hours
Excretionurine (<1%)
Identifiers
  • 5-chloro-3H-benzooxazol-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.186
Chemical and physical data
FormulaC7H4ClNO2
Molar mass169.56 g·mol−1
3D model (JSmol)
  • Clc2cc1c(OC(=O)N1)cc2
  • InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10) Y
  • Key:TZFWDZFKRBELIQ-UHFFFAOYSA-N Y
  (verify)

Chlorzoxazone (INN) is a centrally acting muscle relaxant used to treat muscle spasm and the resulting pain or discomfort. It can also be administered for acute pain in general and for tension headache (muscle contraction headache). It acts on the spinal cord by depressing reflexes. It is sold under the brand names Lorzone, Paraflex and Muscol and in combination form as Parafon Forte, a combination of chlorzoxazone and acetaminophen (paracetamol). Possible side effects include dizziness, lightheadedness, malaise, nausea, vomiting. In rare cases, chlorzoxazone may cause severe liver dysfunction.[3] Conversely, chlorzoxazone may reduce the liver toxicity of acetaminophen by competitive inhibition.[4]

It is available as a generic medication.[5]

Pharmacology

The mechanism of action of chlorzoxazone is thought to be primarily as an opener of BKCa, SKCa and IKCa calcium-activated potassium channels.[6][7][8][9] General central nervous system depression is the only currently accepted aspect to its medical benefits. Elucidation of the exact mechanism of action is ongoing but there is limited study due to the existence of more effective, safe muscle relaxants (e.g., diazepam, cyclobenzaprine, tizanidine), greatly limiting the potential benefit of identifying novel compounds which share chlorzoxazone's mechanism of action.

See also

References

  1. ^ "Parafon DSC- chlorzoxazone tablet". DailyMed. 9 February 2010. Retrieved 5 November 2020.
  2. ^ "Lorzone- chlorzoxazone tablet". DailyMed. 21 June 2019. Retrieved 5 November 2020.
  3. ^ "Chlorzoxazone". LiverTox. National Institute of Diabetes and Digestive and Kidney Diseases. 2017-01-30. PMID 31643467. Retrieved 2024-05-10.
  4. ^ Pingili RB, Vemulapalli S, Gadamsetty MV, Presingu D, Katuri R, Rachamsetty V, et al. (2023-04-17). "Chlorzoxazone reduced the paracetamol-induced toxicity via competitive inhibition of CYP2E1-mediated metabolism". Future Journal of Pharmaceutical Sciences. 9 (1) 34. doi:10.1186/s43094-023-00484-2. ISSN 2314-7253.
  5. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  6. ^ Liu YC, Lo YK, Wu SN. Stimulatory effects of chlorzoxazone, a centrally acting muscle relaxant, on large conductance calcium-activated potassium channels in pituitary GH3 cells. Brain Res. 2003 Jan 3;959(1):86-97. doi:10.1016/s0006-8993(02)03730-7 PMID 12480161
  7. ^ Masi A, Narducci R, Mannaioni G. Harnessing ionic mechanisms to achieve disease modification in neurodegenerative disorders. Pharmacol Res. 2019 Sep;147:104343. doi:10.1016/j.phrs.2019.104343 PMID 31279830
  8. ^ Ferraguto C, Piquemal-Lagoueillat M, Lemaire V, Moreau MM, Trazzi S, Uguagliati B, Ciani E, Bertrand SS, Louette E, Bontempi B, Pietropaolo S. Therapeutic efficacy of the BKCa channel opener chlorzoxazone in a mouse model of Fragile X syndrome. Neuropsychopharmacology. 2024 Dec;49(13):2032-2041. doi:10.1038/s41386-024-01956-6 PMID 39223257
  9. ^ A Technical Guide to the Cellular Effects of Chlorzoxazone on Intracellular Calcium Signaling

Further reading

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