Identification

Name
Methocarbamol
Accession Number
DB00423  (APRD01102)
Type
Small Molecule
Groups
Approved, Vet 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
Synonyms
  • (RS)-2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate
  • Delaxin
  • Methocarbamol
  • Méthocarbamol
  • Methocarbamolum
  • Metocarbamol
  • Metocarbamolo
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MethocarbamolTablet750 mg/1OralVintage Pharmaceuticals, LLC2007-09-132007-09-13Us
MethocarbamolTablet500 mg/1OralLannett Company, Inc.2007-06-19Not applicableUs
MethocarbamolTablet500 mg/1OralVintage Pharmaceuticals, LLC2007-09-132007-09-13Us
MethocarbamolTablet750 mg/1OralLannett Company, Inc.2007-06-19Not applicableUs
Methocarbamol Inj 100mg/mlLiquid100 mgIntramuscular; IntravenousUnivet Pharmaceuticals Ltd.1988-12-31Not applicableCanada
Methocarbamol OmegaLiquid100 mgIntramuscular; IntravenousOmega Laboratories Ltd2003-07-28Not applicableCanada
Robaximol Inj 100mg/mlLiquid100 mgIntramuscular; IntravenousMontreal Veterinary Products Inc.1989-12-31Not applicableCanada
RobaxinInjection100 mg/1mLIntramuscular; IntravenousWest-Ward Pharmaceuticals Corp.1959-06-16Not applicableUs
RobaxinTablet, film coated750 mg/1OralPd Rx Pharmaceuticals, Inc.2003-01-202016-12-15Us
RobaxinTablet, film coated500 mg/1OralUcb Inc2003-01-152013-01-17Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Methocarb 500-EZSKit500 mg/1PureTek Corporation2018-10-23Not applicableUs
MethocarbamolTablet750 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2003-01-29Not applicableUs00603 4486 28 nlmimage10 ee08f707
MethocarbamolTablet500 mg/1OralNucare Pharmaceuticals,inc.2000-01-01Not applicableUs
MethocarbamolTablet750 mg/1OralSolco Healthcare Llc2013-01-15Not applicableUs43547 0226 50 nlmimage10 ae40d766
MethocarbamolTablet750 mg/1OralHetero Drugs Limited Unit III2009-11-06Not applicableUs
MethocarbamolTablet500 mg/1OralRemedy Repack2016-02-092016-11-28Us
MethocarbamolTablet750 mg/1OralPar Pharmaceutical2003-01-29Not applicableUs0603 448620180913 8702 o1c5db
MethocarbamolTablet750 mg/1OralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs53808 095620180907 15195 m4jz2t
MethocarbamolTablet500 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2003-01-29Not applicableUs
MethocarbamolTablet750 mg/1OralUnit Dose Services2013-03-20Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RobaxinTablet500 mgOralPfizer Laboratories Div Pfizer Inc.1958-12-31Not applicableCanada
Robaxin 750Tablet750 mgOralPfizer Laboratories Div Pfizer Inc.1993-12-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
A.S.A. With Methocarbamol Night-time Extra StrengthMethocarbamol (400 mg) + Acetylsalicylic acid (500 mg)TabletOralPharmetics (2011) Inc.Not applicableNot applicableCanada
Acetaminophen 325mg + Methocarbamol 400mg CapletsMethocarbamol (400 mg) + Acetaminophen (325 mg)TabletOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Acetaminophen 500mg + Methocarbamol 400mg Extra Strength CapletsMethocarbamol (400 mg) + Acetaminophen (500 mg)TabletOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Advil Back PainMethocarbamol (500 mg) + Ibuprofen (200 mg)TabletOralPfizer Laboratories Div Pfizer Inc.Not applicableNot applicableCanada
Analgesic and Muscle RelaxantMethocarbamol (500 mg) + Ibuprofen (400 mg)TabletOralPharmascience Inc2012-03-20Not applicableCanada
Analgesic and Muscle Relaxant CapletsMethocarbamol (500 mg) + Ibuprofen (200 mg)TabletOralTeva2009-11-18Not applicableCanada
Aspirin BackacheMethocarbamol (400 mg) + Acetylsalicylic acid (325 mg)TabletOralBayerNot applicableNot applicableCanada
Aspirin Night-timeMethocarbamol (400 mg) + Acetylsalicylic acid (500 mg)TabletOralBayer Inc Consumer Care2006-05-242010-08-05Canada
Axacet-C1/8Methocarbamol (400 mg) + Acetaminophen (325 mg) + Codeine phosphate (8 mg)TabletOralTechnilab Pharma Inc.Not applicableNot applicableCanada
Axisal-C1/8Methocarbamol (400 mg) + Acetylsalicylic acid (325 mg) + Codeine phosphate (8 mg)TabletOralTechnilab Pharma Inc.Not applicableNot applicableCanada
International/Other Brands
Bolaxin (Ying Yuan) / Carbaflex (Paill) / Delaxin / DoloVisan (Dr.Kade Pharmaceutische Fabrik) / Fubaxin (Grape King) / Lumirelax (Juvise) / Metocarbamol (AZ Pharma) / Mioflex (Labinco) / Miorel (Cheminter) / Musxan (Pharmasant) / Ortoton (Recordati) / Rebamol (Winston) / Robaxin / Robaxin-750 (Pfizer) / Robinax (Khandelwal) / Sinaxar (Armofar) / Taspan (Honten)
Categories
UNII
125OD7737X
CAS number
532-03-6
Weight
Average: 241.2405
Monoisotopic: 241.095022595
Chemical Formula
C11H15NO5
InChI Key
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)
IUPAC Name
2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate
SMILES
COC1=CC=CC=C1OCC(O)COC(N)=O

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.

Associated 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.

TargetActionsOrganism
NCarbonic anhydrase 1
inhibitor
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Methocarbamol is combined with 7-Nitroindazole.
AcepromazineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with Aceprometazine.
AcetazolamideThe risk or severity of adverse effects can be increased when Methocarbamol is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Methocarbamol is combined with Acetophenazine.
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

References

General References
  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:2253675]
External Links
Human Metabolome Database
HMDB0014567
KEGG Drug
D00402
PubChem Compound
4107
PubChem Substance
46507761
ChemSpider
3964
ChEBI
77498
ChEMBL
CHEMBL1201117
PharmGKB
PA164749506
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Methocarbamol
ATC Codes
M03BA53 — Methocarbamol, combinations excl. psycholepticsM03BA03 — MethocarbamolM03BA73 — Methocarbamol, combinations with psycholeptics
AHFS Codes
  • 12:20.04 — Centrally Acting Skeletal Muscle Relaxants
FDA label
Download (121 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentPain NOS1
3RecruitingTreatmentLiver Cirrhosis1
4CompletedTreatmentBack Pain Lower Back1
4RecruitingTreatmentRib Fractures / Wounds and Injuries1

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
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apical Pharmaceutical Corporation
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Baxter International Inc.
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Cardinal Health
  • Caremark LLC
  • Carlisle Laboratories Inc.
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Direct Dispensing Inc.
  • DispenseXpress Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Group Health Cooperative
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hetero Drugs Ltd.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Marisol Corp.
  • Martin Surgical Supply
  • Mckesson Corp.
  • Medisca Inc.
  • Merit Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Schein Pharmaceutical Inc.
  • Schwarz Pharma Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Talbert Medical Management Corp.
  • United Research Laboratories Inc.
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
Kit500 mg/1
InjectionIntramuscular; Intravenous100 mg/1mL
Injection, solutionIntramuscular; Intravenous1000 mg/10mL
TabletOral500 mg/1
TabletOral750 mg/1
Tablet, coatedOral500 mg/1
Tablet, coatedOral750 mg/1
TabletOral
Injection, solutionIntramuscular; Intravenous100 mg/1mL
TabletOral500 mg
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral750 mg/1
TabletOral750 mg
LiquidIntramuscular; Intravenous100 mg
Prices
Unit descriptionCostUnit
Robaxin-750 750 mg tablet2.48USD tablet
Robaxin 100 mg/ml vial2.2USD ml
Robaxin-750 tablet1.99USD tablet
Robaxin 500 mg tablet1.68USD tablet
Methocarbamol powder0.95USD g
Methocarbamol 750 mg tablet0.49USD tablet
Methocarbamol 500 mg tablet0.38USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)93 °CPhysProp
water solubility7200 mg/L (at 25 °C)CHEM INSPECT TEST INST (1992)
logP0.61CHEM INSPECT TEST INST (1992)
Predicted Properties
PropertyValueSource
Water Solubility4.21 mg/mLALOGPS
logP0.63ALOGPS
logP0.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.6ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.01 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity59.07 m3·mol-1ChemAxon
Polarizability24.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9638
Blood Brain Barrier+0.5747
Caco-2 permeable-0.6689
P-glycoprotein substrateNon-substrate0.6452
P-glycoprotein inhibitor INon-inhibitor0.9411
P-glycoprotein inhibitor IINon-inhibitor0.8887
Renal organic cation transporterNon-inhibitor0.9105
CYP450 2C9 substrateNon-substrate0.8431
CYP450 2D6 substrateNon-substrate0.7658
CYP450 3A4 substrateNon-substrate0.606
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9302
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9066
CYP450 3A4 inhibitorNon-inhibitor0.9338
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9542
Ames testNon AMES toxic0.5776
CarcinogenicityNon-carcinogens0.9406
BiodegradationNot ready biodegradable0.8358
Rat acute toxicity2.2930 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.984
hERG inhibition (predictor II)Non-inhibitor0.9411
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-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02t9-0900000000-97aeacf66e8410c23139
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02t9-2900000000-df41a784aa756b8e064d

Taxonomy

Description
This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Carbamate esters / Secondary alcohols / Organic carbonic acids and derivatives / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Phenoxy compound / Anisole / Methoxybenzene / Alkyl aryl ether / Monocyclic benzene moiety / Carbamic acid ester / Carbonic acid derivative / Secondary alcohol / Ether / Alcohol
show 9 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carbamate ester, aromatic ether, secondary alcohol (CHEBI:77498)

Targets

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
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:1460006]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 00:42