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Identification
NameCarisoprodol
Accession NumberDB00395  (APRD00417)
TypeSmall Molecule
GroupsApproved
Description

A centrally acting skeletal muscle relaxant whose mechanism of action is not completely understood but may be related to its sedative actions. 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, p1202)

Structure
Thumb
Synonyms
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate
(1-Methylethyl)carbamic acid 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl ester
(RS)-2-{[(aminocarbonyl)oxy]methyl}-2-methylpentyl isopropylcarbamate
2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate
2-Methyl-2-propyltrimethylene carbamate isopropylcarbamate
Carbamic acid 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl ester
Carisoprodate
Carisoprodol
Carisoprodolum
Isobamate
Isomeprobamate
Isopropyl meprobamate
Isopropylmeprobamate
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamate
Someprobamate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carisoprodoltablet250 mg/1oralWallace Pharmaceuticals Inc.2010-07-01Not applicableUs
Somatablet350 mg/1oralMeda Pharmaceuticals Inc.1959-07-01Not applicableUs
Somatablet250 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2007-09-01Not applicableUs
Somatablet250 mg/1oralRebel Distributors Corp2007-09-01Not applicableUs
Somatablet250 mg/1oralSTAT Rx USA LLC2007-09-01Not applicableUs
Somatablet250 mg/1oralMeda Pharmaceuticals Inc.2007-09-01Not applicableUs
Soma Tablets 350mgtablet350 mgoralCarter Horner Corp.1962-12-312003-03-14Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carisoprodoltablet350 mg/1oralPd Rx Pharmaceuticals, Inc.1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralAmerican Health Packaging2010-01-15Not applicableUs
Carisoprodoltablet350 mg/1oralbryant ranch prepack1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralCardinal Health2010-10-08Not applicableUs
Carisoprodoltablet350 mg/1oralCarlsbad Technology, Inc.2014-01-27Not applicableUs
Carisoprodoltablet350 mg/1oralKeltman Pharmaceuticals Inc.2007-08-10Not applicableUs
Carisoprodoltablet350 mg/1oralSTAT Rx USA LLC1996-01-24Not applicableUs
Carisoprodoltablet350 mg/1oralAidarex Pharmaceuticals LLC2010-08-30Not applicableUs
Carisoprodoltablet350 mg/1oralWest Ward Pharmaceuticals Corp1996-01-24Not applicableUs
Carisoprodoltablet350 mg/1oralCardinal Health2010-01-15Not applicableUs
Carisoprodoltablet350 mg/1oralNorthwind Pharmaceuticals2014-06-01Not applicableUs
Carisoprodoltablet350 mg/1oralApotheca Inc.1991-10-17Not applicableUs
Carisoprodoltablet350 mg/1oralVensun Pharmaceuticals, Inc.2014-07-31Not applicableUs
Carisoprodoltablet350 mg/1oralSTAT Rx USA LLC1996-01-24Not applicableUs
Carisoprodoltablet350 mg/1oralDispensing Solutions, Inc.1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralUnit Dose Services2007-02-27Not applicableUs
Carisoprodoltablet350 mg/1oralAphena Pharma Solutions Tennessee, Llc1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralbryant ranch prepack1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralBlenheim Pharmacal, Inc.2011-01-31Not applicableUs
Carisoprodoltablet350 mg/1oralPhysicians Total Care, Inc.1996-04-04Not applicableUs
Carisoprodoltablet350 mg/1oralScie Gen Pharmaceuticals, Inc.2014-01-27Not applicableUs
Carisoprodoltablet350 mg/1oralRed Pharm Drug Inc.1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralProficient Rx LP1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralOrient Pharma Co., Ltd.2015-06-01Not applicableUs
Carisoprodoltablet350 mg/1oralRebel Distributors Corp2007-02-27Not applicableUs
Carisoprodoltablet350 mg/1oralBlenheim Pharmacal, Inc.2012-10-15Not applicableUs
Carisoprodoltablet350 mg/1oralA S Medication Solutions Llc1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralA S Medication Solutions Llc2007-02-27Not applicableUs
Carisoprodoltablet350 mg/1oralDispensing Solutions, Inc.1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralProficient Rx LP2014-06-01Not applicableUs
Carisoprodoltablet350 mg/1oralLife Line Home Care Services, Inc1987-11-01Not applicableUs
Carisoprodoltablet350 mg/1oralLake Erie Medical DBA Quality Care Products LLC2007-02-27Not applicableUs
Carisoprodoltablet350 mg/1oralBlenheim Pharmacal, Inc.2011-02-02Not applicableUs
Carisoprodoltablet350 mg/1oralA S Medication Solutions Llc1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralA S Medication Solutions Llc2007-02-27Not applicableUs
Carisoprodoltablet350 mg/1oralAurobindo Pharma Limited2009-08-06Not applicableUs
Carisoprodoltablet350 mg/1oralSun Pharmaceutical Industries Limited2007-02-27Not applicableUs
Carisoprodoltablet350 mg/1oralBionpharma Inc.2015-04-01Not applicableUs
Carisoprodoltablet350 mg/1oralMutual Pharmaceutical Company, Inc.1991-10-17Not applicableUs
Carisoprodoltablet350 mg/1oralREMEDYREPACK INC.2013-05-09Not applicableUs
Carisoprodoltablet350 mg/1oralRising Pharmaceuticals, Inc.2010-07-01Not applicableUs
Carisoprodoltablet350 mg/1oralDIRECT RX2014-01-01Not applicableUs
Carisoprodoltablet350 mg/1oralPreferred Pharmaceuticals, Inc.2015-05-01Not applicableUs
Carisoprodoltablet350 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1996-01-24Not applicableUs
Carisoprodoltablet350 mg/1oralQualitest Pharmaceuticals1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralH.J. Harkins Company, Inc.1996-01-24Not applicableUs
Carisoprodoltablet350 mg/1oralREMEDYREPACK INC.2013-04-03Not applicableUs
Carisoprodoltablet350 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation1997-09-08Not applicableUs
Carisoprodoltablet350 mg/1oralGolden State Medical Supply, Inc.2014-02-20Not applicableUs
Carisoprodoltablet350 mg/1oralPreferred Pharmaceuticals, Inc.2013-11-13Not applicableUs
Carisoprodoltablet350 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1987-11-01Not applicableUs
Carisoprodoltablet350 mg/1oralWatson Laboratories, Inc.1987-11-01Not applicableUs
Carisoprodoltablet350 mg/1oralMirror Pharmaceuticals LLC2011-08-22Not applicableUs
Carisoprodoltablet350 mg/1oralMedsource Pharmaceuticals2007-02-27Not applicableUs
Carisoprodoltablet350 mg/1oralbryant ranch prepack1987-11-01Not applicableUs
Carisoprodoltablet350 mg/1oralPd Rx Pharmaceuticals, Inc.1987-11-01Not applicableUs
Carisoprodoltablet350 mg/1oralDIRECT RX2016-04-01Not applicableUs
Carisoprodoltablet350 mg/1oralPreferred Pharmaceuticals, Inc.2011-06-15Not applicableUs
Carisoprodoltablet350 mg/1oralRx Change Co.2010-07-01Not applicableUs
Carisoprodoltablet350 mg/1oralWest ward Pharmaceutical Corp1996-01-24Not applicableUs
Carisoprodol Immediate Releasetablet250 mg/1oralVensun Pharmaceuticals, Inc2015-11-20Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CarisomaNot Available
GencariGenovate
GenesafeGenovate
HiraninHwang's
ListaflexFinadiet
SanomaNot Available
TensaprinNewport
Brand mixtures
NameLabellerIngredients
Carisoprodol and AspirinEon Labs, Inc.
Carisoprodol, Aspirin and Codeine PhosphateEon Labs, Inc.
SaltsNot Available
Categories
UNII21925K482H
CAS number78-44-4
WeightAverage: 260.33
Monoisotopic: 260.173607266
Chemical FormulaC12H24N2O4
InChI KeyInChIKey=OFZCIYFFPZCNJE-UHFFFAOYSA-N
InChI
InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
IUPAC Name
2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
SMILES
CCCC(C)(COC(N)=O)COC(=O)NC(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monocarboxylic acids and derivatives. These are carboxylic acids containing exactly one carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassMonocarboxylic acids and derivatives
Direct ParentMonocarboxylic acids and derivatives
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the relief of discomfort associated with acute, painful, musculoskeletal conditions.
PharmacodynamicsCarisoprodol is used as a skeletal muscle relaxant. One of its metabolites, meprobamate, is available as an anxiolytic agent.
Mechanism of actionCarisoprodol is a central nervous system depressant that acts as a sedative and skeletal muscle relaxant. Rather than acting directly on skeletal muscle, carisoprodol interrupts neuronal communication within the reticular formation and spinal cord, resulting in sedation and alteration in pain perception. Its exact mechanism of action is not yet known.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding60%
Metabolism

Hepatic. Metabolized in the liver via the cytochrome P450 oxidase isozyme CYP2C19.

Route of eliminationCarisoprodol is eliminated by both renal and non-renal routes.
Half life8 hours
Clearance
  • oral cl=0.772 L/hour/kg [Women]
  • oral cl=0.38 L/hour/kg [Men]
ToxicitySymptoms of overdose include drowsiness, giddiness, nausea, indigestion, or rash. Other adverse effects attributed to therapeutic use of carisoprodol include dizziness, irritability, insomnia, diplopia, temporary loss of vision, ataxia, weakness, headache, and dysarthria. Non-CNS adverse effects include gastrointestinal complaints, tachycardia, and postural hypotension. Patients sensitive to sulfites or tartrazine may experience wheezing, allergic rashes including erythema multiforme, or anaphylaxis after using some preparations of carisoprodol which contain such additives
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9626
Blood Brain Barrier+0.9679
Caco-2 permeable-0.5533
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8014
P-glycoprotein inhibitor IINon-inhibitor0.8381
Renal organic cation transporterNon-inhibitor0.9519
CYP450 2C9 substrateNon-substrate0.9041
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6418
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8659
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6872
BiodegradationNot ready biodegradable0.973
Rat acute toxicity2.3261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9957
hERG inhibition (predictor II)Non-inhibitor0.9362
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Meda pharmaceuticals meda pharmaceuticals inc
  • Able laboratories inc
  • Actavis totowa llc
  • Advent pharmaceuticals inc
  • Aurobindo pharma ltd
  • Concord laboratories inc
  • Corepharma llc
  • Mutual pharmaceutical co inc
  • Pioneer pharmaceuticals inc
  • Sandoz inc
  • Sun pharmaceutical industries ltd
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Schering corp sub schering plough corp
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Tabletoral250 mg/1
Tabletoral350 mg/1
Tabletoral350 mg
Prices
Unit descriptionCostUnit
Soma 350 mg tablet5.75USD tablet
Soma Compound 200-325 mg tablet4.58USD tablet
Soma 250 mg tablet3.24USD tablet
Carisoprodol powder1.17USD g
Carisoprodol 350 mg tablet0.57USD tablet
Flexall plus gel0.08USD g
Flexall 16% gel0.06USD g
Flexall 7% gel0.05USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point89-91Berger, F.M. and Ludwig, B.J.; U S . Patent 2,937,119; May 17,1960; assigned to Carter Products, Inc.
water solubility300 mg/L (at 25 °C)MERCK INDEX (1996)
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.792 mg/mLALOGPS
logP1.76ALOGPS
logP1.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity67.1 m3·mol-1ChemAxon
Polarizability28.77 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0a4l-9200000000-84ceb4ca447a62939b63View in MoNA
References
Synthesis Reference

Berger, F.M. and Ludwig, B.J.; U S . Patent 2,937,119; May 17,1960; assigned to Carter
Products, Inc.

General References
  1. Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. [PubMed:15530999 ]
  2. Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. [PubMed:15276195 ]
  3. Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6. [PubMed:8322081 ]
External Links
ATC CodesM03BA02M03BA52M03BA72
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (84.9 KB)
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
Acetylsalicylic acidThe serum concentration of the active metabolites of Carisoprodol can be increased when Carisoprodol is used in combination with Acetylsalicylic acid.
AzelastineCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Carisoprodol.
BortezomibThe metabolism of Carisoprodol can be decreased when combined with Bortezomib.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
BuprenorphineCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
DabrafenibThe serum concentration of Carisoprodol can be decreased when it is combined with Dabrafenib.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
EthanolCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FluvoxamineThe metabolism of Carisoprodol can be decreased when combined with Fluvoxamine.
HydrocodoneCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Carisoprodol.
LuliconazoleThe serum concentration of Carisoprodol can be increased when it is combined with Luliconazole.
LumacaftorThe serum concentration of Carisoprodol can be decreased when it is combined with Lumacaftor.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
MethotrimeprazineCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MetyrosineCarisoprodol may increase the sedative activities of Metyrosine.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
MirtazapineCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
OrphenadrineCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
ParaldehydeCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Carisoprodol is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
PhenytoinThe metabolism of Carisoprodol can be increased when combined with Phenytoin.
PramipexoleCarisoprodol may increase the sedative activities of Pramipexole.
RopiniroleCarisoprodol may increase the sedative activities of Ropinirole.
RotigotineCarisoprodol may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Carisoprodol.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
St. John's WortThe serum concentration of the active metabolites of Carisoprodol can be increased when Carisoprodol is used in combination with St. John's Wort.
SuvorexantCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
ThalidomideCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZolpidemCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 02, 2014 14:27