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Identification
Name Methocarbamol
Accession Number DB00423 (APRD01102)
Type small molecule
Groups approved
Description

A centrally acting muscle relaxant whose mode of action has not been established. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1206)

Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • AHR 85
  • Avetil
  • Delaxin
  • Etroflex
  • Forbaxin
  • Glycerylguaiacolate carbamate
  • Glycerylguajacol-Carbamat
  • Guaiacol glyceryl ether carbamate
  • Guaiphenesin carbamate
  • Guaiphenesine carbamate
  • Lumirelax
  • Methocal
  • Metocarbamol
  • Metocarbamolo
  • Metofenia
  • Metofenina
  • Miolaxene
  • Miorilas
  • Miowas
  • Myolaxene
  • Neuraxin
  • Parabaxin
  • Perilax
  • Reflexyn
  • Relestrid
  • Robamol
  • Robaxan
  • Robaxin
  • Robaxine
  • Robaxon
  • Robinax
  • Romethocarb
  • Surquetil
  • Traumacut
  • Tresortil
Brand name mixtures
  • Extra Strength Muscle & Back Pain ASA (Acetylsalicylic acid + Methocarbamol)
  • Methoxacet Extra Strength (Acetaminophen + Methocarbamol)
  • Muscle & Back Pain ASA (Acetylsalicylic acid + Methocarbamol)
  • Muscle & Back Pain Relief Caplets (Acetaminophen + Methocarbamol)
  • Muscle & Back Pain Relief Extra Strength (Acetylsalicylic acid + Methocarbamol)
  • Muscle and Back Pain Relief with Asa (Acetylsalicylic acid + Methocarbamol)
  • Muscle and Back Pain Relief-8 (Acetaminophen + Codeine Phosphate + Methocarbamol)
  • Muscle Relaxant and Analgesic (Acetylsalicylic acid + Methocarbamol)
  • Robaxacet (Methocarbamol + Acetaminophen)
Categories
  • Muscle Relaxants, Central
CAS number 532-03-6
Weight Average: 241.2405
Monoisotopic: 241.095022595
Chemical Formula C11H15NO5
InChI Key InChIKey=GNXFOGHNGIVQEH-UHFFFAOYSA-N
InChI
InChI=1S/C11H15NO5/c1-15-9-4-2-3-5-10(9)16-6-8(13)7-17-11(12)14/h2-5,8,13H,6-7H2,1H3,(H2,12,14)
Plain Text
IUPAC Name
2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate
SMILES
COC1=C(OCC(O)COC(N)=O)C=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbamates and Derivatives
  • Phenols and Derivatives
  • Ethers
  • Catechols
  • Anisoles
  • Phenyl Esters
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Carbamates and Derivatives
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Catechols
  • Aromatic compounds
  • Anisoles
  • Alcohols and Polyols
  • Phenyl Esters
Pharmacology
Indication For use as an adjunct to rest, physical therapy, and other measures for the relief of discomforts associated with acute, painful musculoskeletal conditions.
Pharmacodynamics Methocarbamol is a central muscle relaxant for skeletal muscles, used to treat spasms. It is structurally related to guaifenesin. Methocarbamol's exact mechanism of causing skeletal muscle relaxation is unknown. It is thought to work centrally, perhaps by general depressant effects. It has no direct relaxant effects on striated muscle, nerve fibers, or the motor endplate. It will not directly relax contracted skeletal muscles. The drug has a secondary sedative effect.
Mechanism of action The mechanism of action of methocarbamol in humans has not been established, but may be due to central nervous system depression. It has no direct action on the contractile mechanism of striated muscle, the motor end plate or the nerve fiber.
Absorption Rapid. Onset of action is about 30 minutes after oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic.

Route of elimination Small amounts of unchanged methocarbamol also are excreted in the urine.
Half life 1.14-1.24 hours
Clearance
  • 0.2 – 0.8 L/h/kg [healthy]
Toxicity Symptoms of overdose include blurred vision, coma, drowsiness, low blood pressure, nausea, and seizures.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Marsam pharmaceuticals llc
  • Watson laboratories inc
  • Baxter healthcare corp anesthesia critical care
  • Ferndale laboratories inc
  • Forest laboratories inc
  • Able laboratories inc
  • American therapeutics inc
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Clonmel healthcare ltd
  • Heather drug co inc
  • Hetero drugs ltd
  • Impax laboratories inc
  • Inwood laboratories inc sub forest laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kv pharmaceutical co
  • Lannett co inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Nylos trading co inc
  • Pharmeral inc
  • Pioneer pharmaceuticals inc
  • Purepac pharmaceutical co
  • Roxane laboratories inc
  • Sandoz inc
  • Solco healthcare us llc
  • Solvay pharmaceuticals
  • Superpharm corp
  • Tablicaps inc
  • Upsher smith laboratories inc
  • Vintage pharmaceuticals inc
  • West ward pharmaceutical corp
  • Schwarz pharma inc
Packagers
Dosage forms
Form Route Strength
Liquid Intramuscular
Liquid Intravenous
Tablet Oral
Prices
Unit description Cost Unit
Robaxin-750 750 mg tablet 2.48 USD tablet
Robaxin 100 mg/ml vial 2.2 USD ml
Robaxin-750 tablet 1.99 USD tablet
Robaxin 500 mg tablet 1.68 USD tablet
Methocarbamol powder 0.95 USD g
Methocarbamol 750 mg tablet 0.49 USD tablet
Methocarbamol 500 mg tablet 0.38 USD tablet
Patents Not Available
Properties
State solid
Melting point 93 oC
Experimental Properties
Property Value Source
water solubility 7200 mg/L PhysProp
logP 0.1 PhysProp
Predicted Properties
Property Value Source
water solubility 4.21e+00 g/l ALOGPS
logP 0.63 ALOGPS
logP 0.45 ChemAxon Molconvert
logS -1.76 ALOGPS
pKa 14.81 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 91.01 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 59.07 ChemAxon Molconvert
polarizability 24.24 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Sica DA, Comstock TJ, Davis J, Manning L, Powell R, Melikian A, Wright G: Pharmacokinetics and protein binding of methocarbamol in renal insufficiency and normals. Eur J Clin Pharmacol. 1990;39(2):193-4. Pubmed
External Links
Resource Link
KEGG Drug D00402 Link_out
PubChem Compound 4107 Link_out
PubChem Substance 46507761 Link_out
ChemSpider 3964 Link_out
PharmGKB PA450424 Link_out
Drug Product Database 731110 Link_out
RxList http://www.rxlist.com/cgi/generic/methocar.htm Link_out
Drugs.com http://www.drugs.com/methocarbamol.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/rob1384.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Methocarbamol Link_out
ATC Codes
  • M03BA03
AHFS Codes
  • 12:20.00
PDB Entries Not Available
FDA label show (121.1 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.
Targets

1. Carbonic anhydrase 1

Pharmacological action: no
Actions: inhibitor

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: P00915 Link_out
Gene: CA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on December 22, 2010 09:09

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.