Metabolism of Metaxalone

Bruce, Robert; Turnbull, Lennox B.; Newman, Jack; Pitts, Jefferson E.

doi:10.1021/jm00321a004

Cited by 41 publications

(19 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As reported for metaxalone and mephenoxalone (Bruce et al 1966, Morrison 1965, the oxazolidinone moiety of the molecule appears to be metabolically stable.…”

Section: Discussionmentioning

confidence: 51%

See 1 more Smart Citation

Metabolic fate of 3-(3-methylphenyl)-5-hydroxymethyl-2-oxazolidinone (toloxatone), a new antidepressant agent, in man

Malnoë¹,

Ms²

1979

Xenobiotica

View full text Add to dashboard Cite

1. In man, the antidepressant agent 3-(3-methylphenyl)-5-hydroxymethyl-2-oxazolidinone (toloxatone) on oral dosing was mainly eliminated in urine (80% dose in 12 h). 2. Plasma concn. of total radioactivity was max (5.8 micrograms equiv./ml) at 30 min to 1 h after administration and declined rapidly (t1/2, 1.25 h). Unchanged drug accounted for 48, 32 and 13% of plasma radioactivity at 15 min, 1 h and 6 h, respectively. 3. The drug was extensively metabolized. The major urinary metabolites were 3-(3-carboxyphenyl)-5-hydroxymethyl-2-oxazolidinone and a glucuronide of toloxatone. A minor urinary metabolite, characterized as a phenolic derivative, was also excreted conjugated.

show abstract

“…As reported for metaxalone and mephenoxalone (Bruce et al 1966, Morrison 1965, the oxazolidinone moiety of the molecule appears to be metabolically stable.…”

Section: Discussionmentioning

confidence: 51%

“…Eckardt, Goenechea and Gielsdorf (1977) reported opening of the oxazolidinone ring for mephenoxalone. Hydrolysis of the carbon-oxygen bond of the carbamate would have provided an unstable carbamic acid.…”

Section: Discussionmentioning

confidence: 99%

Metabolic fate of 3-(3-methylphenyl)-5-hydroxymethyl-2-oxazolidinone (toloxatone), a new antidepressant agent, in man

Malnoë¹,

Ms²

1979

Xenobiotica

View full text Add to dashboard Cite

show abstract

“…Metaxalone (15.1.12), is a skeletal muscle relaxant, indicated as an adjunct to rest physical therapy to relax muscles and relieve pain and discomfort caused by muscle injuries (strains, sprains, and other) [9][10][11][12].…”

Section: Metaxalone-skelaxinmentioning

confidence: 99%

Centrally Acting Skeletal Muscle Relaxants

Vardanyan

Hruby

2016

Synthesis of Best-Seller Drugs

View full text Add to dashboard Cite

“…The chemistry of the metabolic products was proposed by Bruce et al . [2]. Metaxalone (marketed by King Pharmaceutical under the brand name SKELAXIN ® , approved by the US FDA in 1962 [3]) is a muscle relaxant and useful to relieve the pain caused by strains, sprains and other musculoskeletal conditions.…”

Section: Introductionmentioning

confidence: 99%

Development of a Stability Indicating RP-UPLC Method for Rapid Determination of Metaxalone and its Degradation Products in Solid Oral Dosage Form

Trivedi

2012

Sci. Pharm.

View full text Add to dashboard Cite

A simple, sensitive and reproducible reversed phase ultra performance liquid chromatography (RP-UPLC) coupled with a photodiode array detector method was developed for the quantitative determination of metaxalone (META) in pharmaceutical dosage forms. The method is applicable to the quantification of related substances and assay of drug product. Chromatographic separation was achieved on an Acquity® HSS-T3 (100 mm x 2.1 mm, 1.7 μm) column. The optimized isocratic mobile phase consists of a mixture of water, methanol, acetonitrile and triethylamine in the ratio of 50:25:25:0.1 % v/v (pH adjusted to 6.3 with orthophosphoric acid). The eluted compounds were monitored at 230 nm for META assay and 205 nm for related substances, the flow rate was 0.3 mL/min, and the column oven temperature was maintained at 45°C. The developed method separated META from its two known and two unknown impurities within 6.0 min. Metaxalone was subjected to the stress conditions of oxidative, acid, base, hydrolytic, thermal and photolytic degradation. Metaxalone was found to degrade significantly in base stress condition, degrade slightly in oxidative stress condition and remain stable in acid, hydrolytic, thermal and photolytic degradation conditions. All impurities were well resolved from each other and from the main peak, showing the stability-indicating power of the method. The developed method was validated as per International Conference on Harmonization (ICH) guidelines.

show abstract

Metabolism of Metaxalone

Cited by 41 publications

References 0 publications

Metabolic fate of 3-(3-methylphenyl)-5-hydroxymethyl-2-oxazolidinone (toloxatone), a new antidepressant agent, in man

Metabolic fate of 3-(3-methylphenyl)-5-hydroxymethyl-2-oxazolidinone (toloxatone), a new antidepressant agent, in man

Centrally Acting Skeletal Muscle Relaxants

Development of a Stability Indicating RP-UPLC Method for Rapid Determination of Metaxalone and its Degradation Products in Solid Oral Dosage Form

Contact Info

Product

Resources

About