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Showing drug card for Carisoprodol (DB00395)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:13
Primary Accession Number DB00395
Secondary Accession Number
  • APRD00417
Name Carisoprodol
Drug Type
  • Approved
  • Small Molecule
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)
Synonyms
  1. Carisoprodate
  2. Carisoprodatum
  3. Isomeprobamate
  4. Isoprotane
  5. Isoprothane
Brand Names
  1. Apesan
  2. Artifar
  3. Arusal
  4. Atonalyt
  5. Caridolin
  6. Carisoma
  7. Chinchen
  8. Fibrosona
  9. Flexagilt
  10. Flexagit
  11. Flexal
  12. Flexartal
  13. Flexidon
  14. Listaflex
  15. Meprodat
  16. Mioartrina
  17. Miolisodal
  18. Mioratrina
  19. Mioril
  20. Muslax
  21. Neotica
  22. Nospasm
  23. Relasom
  24. Sanoma
  25. Scutamil-C
  26. Skutamil
  27. Soma
  28. Somanil
Brand Mixtures Not Available
Chemical IUPAC Name [2-(carbamoyloxymethyl)-2-methylpentyl] N-propan-2-ylcarbamate
Chemical Formula C12H24N2O4
Chemical Structure Structure
CAS Registry Number 78-44-4
InChI Identifier InChI=1/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)/f/h14H,13H2
InChI Key OFZCIYFFPZCNJE-BDCRCPFKCQ
KEGG Drug D00768 Link Image
KEGG Compound C07927 Link Image
PubChem Compound 2576 Link Image
PubChem Substance 10129 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00116629 Link Image
RxList Link http://www.rxlist.com/cgi/generic/carisop.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Carisoprodol Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Berger, Ludwig, U.S. Pat. 2,937,119 (1960)
Average Molecular Weight 260.3300
Monoisotopic Molecular Weight 260.1736
State Solid
Melting Point 92-93 oC
Experimental Water Solubility 0.3 mg/ml Source: PhysProp
Predicted Water Solubility 7.92e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.1 Source: PhysProp
Predicted LogP 1.76 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.52 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCC[C@](C)(COC(N)=O)COC(=O)NC(C)C
Canonical SMILES CCCC(C)(COC(N)=O)COC(=O)NC(C)C
Drug Category
  • Muscle Relaxants
  • Muscle Relaxants, Central
  • Skeletal Muscle Relaxants
ATC Codes
AHFS Codes Not Available
Indication For the relief of discomfort associated with acute, painful, musculoskeletal conditions.
Pharmacology Carisoprodol is used as a skeletal muscle relaxant. One of its metabolites, meprobamate, is available as an anxiolytic agent.
Mechanism of Action The mechanism of action is not known. 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.
Absorption Not Available
Toxicity Symptoms 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
Protein Binding 60%
Biotransformation Hepatic. Metabolized in the liver via the cytochrome P450 oxidase isozyme CYP2C19.
Half Life 8 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV

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.