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Identification
Name Carisoprodol
Accession Number DB00395 (APRD00417)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Carisoprodate
  • Carisoprodatum
  • Isomeprobamate
  • Isoprotane
  • Isoprothane
Brand names
  • Apesan
  • Artifar
  • Arusal
  • Atonalyt
  • Caridolin
  • Carisoma
  • Chinchen
  • Fibrosona
  • Flexagilt
  • Flexagit
  • Flexal
  • Flexartal
  • Flexidon
  • Listaflex
  • Meprodat
  • Mioartrina
  • Miolisodal
  • Mioratrina
  • Mioril
  • Muslax
  • Neotica
  • Nospasm
  • Relasom
  • Sanoma
  • Scutamil-C
  • Skutamil
  • Soma
  • Somanil
Brand name mixtures Not Available
Categories
  • Muscle Relaxants
  • Skeletal Muscle Relaxants
  • Muscle Relaxants, Central
CAS number 78-44-4
Weight Average: 260.33
Monoisotopic: 260.173607266
Chemical Formula C12H24N2O4
InChI Key InChIKey=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)
Plain Text
IUPAC Name
2-methyl-2-({[(propan-2-yl)carbamoyl]oxy}methyl)pentyl carbamate
SMILES
CCCC(C)(COC(N)=O)COC(=O)NC(C)C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbamates and Derivatives
Substructures
  • Carbamates and Derivatives
  • Ethers
Pharmacology
Indication For the relief of discomfort associated with acute, painful, musculoskeletal conditions.
Pharmacodynamics Carisoprodol is used as a skeletal muscle relaxant. One of its metabolites, meprobamate, is available as an anxiolytic agent.
Mechanism of action Carisoprodol 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding 60%
Metabolism

Hepatic. Metabolized in the liver via the cytochrome P450 oxidase isozyme CYP2C19.
Route of elimination Carisoprodol is eliminated by both renal and non-renal routes.
Half life 8 hours
Clearance
  • oral cl=0.772 L/hour/kg [Women]
  • oral cl=0.38 L/hour/kg [Men]
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
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Soma 350 mg tablet 5.75 USD tablet
Soma Compound 200-325 mg tablet 4.58 USD tablet
Soma 250 mg tablet 3.24 USD tablet
Carisoprodol powder 1.17 USD g
Carisoprodol 350 mg tablet 0.57 USD tablet
Flexall plus gel 0.08 USD g
Flexall 16% gel 0.06 USD g
Flexall 7% gel 0.05 USD g
Patents Not Available
Properties
State solid
Melting point 92-93 oC
Experimental Properties
Property Value Source
water solubility 0.3 mg/ml PhysProp
logP 2.1 PhysProp
Predicted Properties
Property Value Source
water solubility 7.92e-01 g/l ALOGPS
logP 1.76 ALOGPS
logP 1.92 ChemAxon Molconvert
logS -2.52 ALOGPS
pKa 15.56 ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 90.65 ChemAxon Molconvert
rotatable bond count 9 ChemAxon Molconvert
refractivity 67.10 ChemAxon Molconvert
polarizability 28.77 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  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
  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
  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
External Links
Resource Link
KEGG Drug D00768 Link_out
KEGG Compound C07927 Link_out
PubChem Compound 2576 Link_out
PubChem Substance 46506377 Link_out
ChemSpider 2478 Link_out
ChEBI 3419 Link_out
ChEMBL 3419 Link_out
Drug Product Database 116629 Link_out
RxList http://www.rxlist.com/cgi/generic/carisop.htm Link_out
Drugs.com http://www.drugs.com/carisoprodol.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Carisoprodol Link_out
ATC Codes
  • M03BA02
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (84.9 KB)
MSDS show (73.3 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.
Enzymes

1. Cytochrome P450 2C19

Actions: substrate

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

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. 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. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:03

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