Metaxalone

Identification

Name
Metaxalone
Accession Number
DB00660  (APRD00514)
Type
Small Molecule
Groups
Approved
Description

Metaxalone (marketed by King Pharmaceuticals under the brand name Skelaxin®) is a muscle relaxant 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 considered to be a moderately strong muscle relaxant, with relatively low incidence of side effects. Skelaxin comes in an 800 mg scored tablet. It previously came in both 400 mg and 800 mg tablets. The 400 mg tablet has been discontinued. Possible side effects include nausea, vomiting, drowsiness and CNS side effects such as dizziness, headache, and irritability.

Structure
Thumb
Synonyms
  • Metassalone
  • Metaxalon
  • Metaxalona
  • Metaxalonum
External IDs
AHR 438
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MetaxaloneTablet800 mg/1OralDispensing Solutions, Inc.2007-11-01Not applicableUs68258 710020180907 15195 10nb02l
MetaxaloneTablet800 mg/1OralRemedy Repack2012-03-292013-04-05Us
MetaxaloneTablet800 mg/1OralRemedy Repack2018-05-07Not applicableUs
MetaxaloneTablet640 mg/1OralCore Pharma, Llc2015-09-302015-09-30Us
MetaxaloneTablet800 mg/1OralCarilion Materials Management2007-11-01Not applicableUs68151 466820180907 15195 vi4v5l
MetaxaloneTablet800 mg/1Oralbryant ranch prepack2007-11-01Not applicableUs63629 276820180913 8702 1nevawj
MetaxaloneTablet800 mg/1Oralbryant ranch prepack2007-11-01Not applicableUs63629 420520180913 8702 2mkggf
MetaxaloneTablet800 mg/1OralBlenheim Pharmacal, Inc.2010-05-20Not applicableUs
MetaxaloneTablet800 mg/1OralA-S Medication Solutions2007-11-012016-04-30Us50090 118020180907 15195 ey0lbd
MetaxaloneTablet800 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2011-12-06Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MetaxallTablet800 mg/1OralSircle Laboratories, Llc2015-09-25Not applicableUs
MetaxaloneTablet800 mg/1OralNorthwind Pharmaceuticals2014-02-12Not applicableUs
MetaxaloneTablet800 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2016-11-22Not applicableUs
MetaxaloneTablet800 mg/1OralPreferreed Pharmaceuticals Inc.2017-10-11Not applicableUs
MetaxaloneTablet800 mg/1OralA-S Medication Solutions2017-06-19Not applicableUs
MetaxaloneTablet800 mg/1OralSciegen Pharmaceuticals Inc.2017-08-31Not applicableUs
MetaxaloneTablet800 mg/1OralRemedy Repack2017-10-09Not applicableUs
MetaxaloneTablet400 mg/1OralImpax Generics2016-05-26Not applicableUs
MetaxaloneTablet800 mg/1OralRebel Distributors2010-03-31Not applicableUs
MetaxaloneTablet800 mg/1Oralbryant ranch prepack2013-05-31Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Lorvatus PharmaPakMetaxalone (800 mg/1) + Diclofenac sodium (16.05 mg/1mL) + Isopropyl Alcohol (0.7 mL/1mL)KitSircle Laboratories, Llc2015-12-012017-12-31Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SkelaxinMetaxalone (400 mg/1)TabletOralKing Pharmaceuticals, Inc.2006-10-082006-10-08Us
International/Other Brands
Skelaxin
Categories
UNII
1NMA9J598Y
CAS number
1665-48-1
Weight
Average: 221.2524
Monoisotopic: 221.105193351
Chemical Formula
C12H15NO3
InChI Key
IMWZZHHPURKASS-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one
SMILES
CC1=CC(OCC2CNC(=O)O2)=CC(C)=C1

Pharmacology

Indication

For the treatment of painful peripheral musculoskeletal conditions and spasticity from upper motor neuron syndromes.

Associated Conditions
Pharmacodynamics

Metaxalone is a skeletal muscle relaxant indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomforts associated with acute, painful musculoskeletal conditions. The mode of action of this drug has not been clearly identified, but may be related to its sedative properties. Metaxalone does not directly relax tense skeletal muscles in man.

Mechanism of action

The mechanism of action of metaxalone in humans has not been established, but may be due to general central nervous system depression.

Absorption

The absolute bioavailability of metaxalone from Skelaxin tablets is not known.

Volume of distribution
  • 800 L
Protein binding
Not Available
Metabolism

Probably hepatic.

Route of elimination

Metaxalone is metabolized by the liver and excreted in the urine as unidentified metabolites.

Half life

9.2 (+/- 4.8) hours

Clearance
  • 68 +/- 50 L/h [Subjects received 1×400mg tablet under fasted conditions]
  • 66 +/- 51 L/h [Subjects received 2×400 mg tablets under fasted conditions]
Toxicity

LD50=775mg/kg (Rat, oral); LD50=1690 mg/kg (Mouse, oral). When determining the LD50 in rats and mice, progressive sedation, hypnosis and finally respiratoryfailure were noted as the dosage increased. In dogs, no LD50 could be determined as the higher doses produced an emetic action in 15 to 30 minutes.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7-NitroindazoleThe risk or severity of adverse effects can be increased when Metaxalone is combined with 7-Nitroindazole.
AcepromazineThe risk or severity of adverse effects can be increased when Metaxalone is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Metaxalone is combined with Aceprometazine.
AcetaminophenAcetaminophen may decrease the excretion rate of Metaxalone which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Metaxalone which could result in a higher serum level.
AdipiplonThe risk or severity of adverse effects can be increased when Metaxalone is combined with Adipiplon.
AgomelatineThe risk or severity of adverse effects can be increased when Metaxalone is combined with Agomelatine.
AlaproclateThe risk or severity of adverse effects can be increased when Metaxalone is combined with Alaproclate.
AlfaxaloneThe risk or severity of adverse effects can be increased when Metaxalone is combined with Alfaxalone.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Metaxalone.
Food Interactions
Not Available

References

Synthesis Reference

Spiridon Spireas, "Bioavailable compositions of metaxalone and processes for producing the same." U.S. Patent US20050276844, issued December 15, 2005.

US20050276844
General References
  1. See S, Ginzburg R: Choosing a skeletal muscle relaxant. Am Fam Physician. 2008 Aug 1;78(3):365-70. [PubMed:18711953]
  2. Elenbaas JK: Centrally acting oral skeletal muscle relaxants. Am J Hosp Pharm. 1980 Oct;37(10):1313-23. [PubMed:6999895]
External Links
Human Metabolome Database
HMDB0014798
KEGG Drug
D00773
KEGG Compound
C07934
PubChem Compound
15459
PubChem Substance
46506253
ChemSpider
14709
ChEBI
6797
ChEMBL
CHEMBL1079604
PharmGKB
PA164747189
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Metaxalone
FDA label
Download (124 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentLow Back Pain (LBP)1

Pharmacoeconomics

Manufacturers
  • Sandoz inc
  • King pharmaceuticals inc
  • Elan Corporation
Packagers
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Blenheim Pharmacal
  • Cardinal Health
  • D.M. Graham Laboratories Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Keltman Pharmaceuticals Inc.
  • King Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Mckesson Corp.
  • Nucare Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prescript Pharmaceuticals
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
Kit
TabletOral400 mg/1
TabletOral640 mg/1
TabletOral800 mg/1
Prices
Unit descriptionCostUnit
Metaxalone 800 mg tablet3.88USD tablet
Skelaxin 800 mg tablet3.84USD tablet
Skelaxin 400 mg tablet0.84USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6407128No2001-12-032021-12-03Us
US7122566No2006-02-062026-02-06Us
US7714006No2001-12-032021-12-03Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)122 °CPhysProp
logP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.28 mg/mLALOGPS
logP1.63ALOGPS
logP2.37ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)13.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.32 m3·mol-1ChemAxon
Polarizability23.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9747
Caco-2 permeable+0.5076
P-glycoprotein substrateNon-substrate0.7072
P-glycoprotein inhibitor INon-inhibitor0.8309
P-glycoprotein inhibitor IINon-inhibitor0.906
Renal organic cation transporterNon-inhibitor0.8464
CYP450 2C9 substrateNon-substrate0.8154
CYP450 2D6 substrateNon-substrate0.7182
CYP450 3A4 substrateNon-substrate0.5649
CYP450 1A2 substrateInhibitor0.6863
CYP450 2C9 inhibitorNon-inhibitor0.7448
CYP450 2D6 inhibitorNon-inhibitor0.7733
CYP450 2C19 inhibitorNon-inhibitor0.6471
CYP450 3A4 inhibitorNon-inhibitor0.911
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.797
Ames testNon AMES toxic0.6074
CarcinogenicityNon-carcinogens0.9312
BiodegradationNot ready biodegradable0.9544
Rat acute toxicity2.4250 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9319
hERG inhibition (predictor II)Non-inhibitor0.913
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0490000000-964e6b5348bafc1182d9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0089-0980000000-2b6e14f3b5e5c19c4e5c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0910000000-c8b21539b07eb2e7d34e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-0f09eb181838526daa7c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-018693fc5b6345ee25c5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-921f9f6e188e7466aa4d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-08fr-4900000000-222616eabf1bcdd48049
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-08fr-6900000000-06981ad91bcbeda7d385
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-6900000000-77e22c24cb4c6bbc81a1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-8900000000-54c62bf2b5c1b70898bb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9700000000-82878fa5fbb78b27ef0b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9500000000-66f674cba4e44834a425

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
m-Xylenes / Phenoxy compounds / Alkyl aryl ethers / Oxazolines / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Phenoxy compound / M-xylene / Xylene / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Oxazoline / Ether / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether (CHEBI:6797)

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 04:25