Metaxalone

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Not to be confused with Metolazone, a diuretic.
Metaxalone
Names
Trade namesSkelaxin, others
  • 5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one
Clinical data
Drug classMuscle relaxant[1]
Main usesMusculoskeletal conditions[2]
Side effectsSleepiness, dizziness, headache, nausea, irritability[2]
Pregnancy
category
  • US: N (Not classified yet)
Routes of
use		By mouth
Onset of actionWithin 1 hr[1]
Duration of actionUp to 6 hrs[1]
External links
AHFS/Drugs.comMonograph
MedlinePlusa682010
Legal
License data
Legal status
Pharmacokinetics
BioavailabilityUnknown
MetabolismLiver
Elimination half-life9.2 (± 4.8) hours
ExcretionKidney
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) checkY
  • Key:IMWZZHHPURKASS-UHFFFAOYSA-N checkY

Metaxalone, sold under the brand name Skelaxin among others, is a muscle relaxant used to treat pain due to musculoskeletal conditions.[2] It has not been found to be useful in cerebral palsy.[1] It is taken by mouth.[1] It may be used together with rest and physiotherapy.[1]

Common side effects include sleepiness, dizziness, headache, nausea, and irritability.[2] Other side effects may include anaphylaxis, rash, jaundice, serotonin syndrome, and low blood cells.[2] Safety in pregnancy is not clear.[2] Exactly how it works is not known, but it may be due to general depression of the central nervous system.[2]

Metaxalone was approved for medical use in the United States in 1962.[1] In the United States 30 tablets costs about 24 USD.[3] There use; however, is not generally recommended.[4]

Medical use

Dosage

It is taken at a dose of 800 mg up to four times per day.[2]

Side effects

Because of the potential for side effects, this drug is considered a high risk in the elderly.[medical citation needed]

Interactions

The metabolism of metaxalone involves enzymes CYP1A2 and CYP2C19 in the cytochrome P450 system.[medical citation needed] 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.[5]

Pharmacokinetics

Metaxalone exhibits increased bioavailability when taken with food.[6] Specifically, in one study, compared to fasted conditions, the presence of food at the time of drug administration increased Cmax by 77.5%, AUC0-t by 23.5%, and AUC0-∞ by 15.4%.[7] Metaxalone is a substrate of CYP1A2 and CYP2C19, an inhibitor of CYP1A2, CYP2B6, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A, and an inducer of CYP1A2 and CYP3A4.[5]

Assay

A literature survey reveals very few methods are reported for the determination of metaxalone to date. Nirogi et al.[7] reported a liquid chromatographic method coupled to tandem mass spectrometry for the quantification of metaxalone in human plasma. A stability-indicating HPLC method was introduced by P.K. Sahu et al.[8] Metaxalone has been used as an internal standard for few analytical methods.[9][10]

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Metaxalone Monograph for Professionals". Drugs.com. Archived from the original on 9 August 2020. Retrieved 17 November 2021.
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 "Skelaxin- metaxalone tablet". DailyMed. 27 April 2018. Archived from the original on 27 October 2020. Retrieved 23 October 2020.
  3. ↑ "Metaxalone Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 25 October 2016. Retrieved 17 November 2021.
  4. ↑ Mitchell, Steve. "Why You Shouldn't Take Soma or Other Muscle Relaxers Every Day". Consumer Reports. Archived from the original on 2020-08-08. Retrieved 2021-11-17.
  5. ↑ 5.0 5.1 "United States Patent No. 7,378,434, by Jie Du, et al". Archived from the original on 2021-10-31. Retrieved 2022-03-14.
  6. ↑ "Skelaxin Package Insert". Archived from the original on 2012-03-11. Retrieved 2021-08-25.
  7. ↑ 7.0 7.1 Nirogi RV, Kandikere VN, Shukla M, Mudigonda K, Shrivastava W, Datla PV (May 2006). "Quantification of Metaxalone in Human Plasma by Liquid Chromatography Coupled to Tandem Mass Spectrometry". J Anal Toxicol. 30 (4): 245–51. doi:10.1093/jat/30.4.245. PMID 16803662.
  8. ↑ Sahu, Prafulla Kumar; Annapurna, M. Mathrusri; Kumar, Sahoo Dillip (2011). "Development and Validation of Stability Indicating RP-HPLC Method for the Determination of Metaxalone in Bulk and its Pharmaceutical Formulations". e-Journal of Chemistry. 8 (s1): S439–S447. doi:10.1155/2011/645710.
  9. ↑ Mistri, HN; Jangid, AG; Pudage, A; Gomes, N; Sanyal, M; Shrivastav, P (15 June 2007). "High throughput LC-MS/MS method for simultaneous quantification of lamivudine, stavudine and nevirapine in human plasma". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 853 (1–2): 320–32. doi:10.1016/j.jchromb.2007.03.047. PMID 17481969.
  10. ↑ Mistri, HN; Jangid, AG; Pudage, A; Shrivastav, P (15 March 2008). "HPLC-ESI-MS/MS validated method for simultaneous quantification of zopiclone and its metabolites, N-desmethyl zopiclone and zopiclone-N-oxide in human plasma". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 864 (1–2): 137–48. doi:10.1016/j.jchromb.2008.02.004. PMID 18313371.

External links

External sites:
Identifiers:
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