Metaxalone

Metaxalone, sold under the brand name Skelaxin, is a muscle relaxant medication used to relax muscles and relieve pain caused by strains, sprains, and other musculoskeletal conditions. Its exact mechanism of action is not known, but it may be due to general central nervous system depression. It is a moderately strong muscle relaxant, with relatively low incidence of side effects.

Metaxalone
Clinical data
Trade namesSkelaxin
AHFS/Drugs.comMonograph
MedlinePlusa682010
License data
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUnknown
MetabolismLiver
Elimination half-life9.2 ± 4.8 hours
ExcretionKidney
Identifiers
  • 5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.015.253
Chemical and physical data
FormulaC12H15NO3
Molar mass221.256 g·mol−1
3D model (JSmol)
  • O=C2OC(COc1cc(cc(c1)C)C)CN2
  • InChI=1S/C12H15NO3/c1-8-3-9(2)5-10(4-8)15-7-11-6-13-12(14)16-11/h3-5,11H,6-7H2,1-2H3,(H,13,14) Y
  • Key:IMWZZHHPURKASS-UHFFFAOYSA-N Y
  (verify)

Common side effects include nausea, vomiting, drowsiness, and central nervous system (CNS) side effects, such as dizziness, headache, and irritability.

The metabolism of metaxalone involves enzymes CYP1A2 and CYP2C19 in the cytochrome P450 system. Because many medications are metabolized by enzymes in this system, precaution must be taken when administering it with other medications involving the P450 system to avoid interactions.

Because of the potential for side effects, this drug is considered high risk in the elderly.

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