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Record Information
Version2.0
Creation Date2009-07-30 17:58:45 UTC
Update Date2014-12-24 20:26:07 UTC
Accession NumberT3D3491
Identification
Common NameCarisoprodol
ClassSmall Molecule
DescriptionA 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)
Compound Type
  • Amine
  • Carbamate
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Muscle Relaxant
  • Muscle Relaxant, Central
  • Muscle Relaxant, Skeletal
  • Neuromuscular Agent
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(+-)-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
Carisoma
Carisoprodate
Carisoprodatum
Carisoprodolum
Gencari
Genesafe
Hiranin
Isobamate
Isomeprobamate
Isopropyl meprobamate
Isopropylmeprobamate
Isoprotane
Isoprothane
Listaflex
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamate
Sanoma
Soma
Someprobamate
Tensaprin
Chemical FormulaC12H24N2O4
Average Molecular Mass260.330 g/mol
Monoisotopic Mass260.174 g/mol
CAS Registry Number78-44-4
IUPAC Name2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
Traditional NameSoma
SMILESCCCC(C)(COC(O)=N)COC(O)=NC(C)C
InChI IdentifierInChI=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)
InChI KeyInChIKey=OFZCIYFFPZCNJE-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCarbamate esters
Alternative Parents
Substituents
  • Carbamic acid ester
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point89-91°C
Boiling PointNot Available
Solubility300 mg/L (at 25°C)
LogP2.1
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP1.76ALOGPS
logP1.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity67.1 m³·mol⁻¹ChemAxon
Polarizability28.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9320000000-ea5623d29b47a08ec316JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-056r-1920000000-df362ad4c912b7d0fb43JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-4910000000-0fe5eef3c39360c36d38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-9300000000-94d7b1adea0d831c0950JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dj-9100000000-a99d65f53726ca3b6116JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-618eb5a23da29ec51cb6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-d2d07fc2a5972fd4e9f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-007521fa65c254bad2b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-1920000000-df362ad4c912b7d0fb43JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-6490000000-046fd220fa245140ddabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9320000000-b08ca9d93b628ea8b4f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-4f09dfa1c188e3251a65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-9010000000-548142f811b5a3632f8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-37215ebd46867ac40f9fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-46650c3ec5dedc27b7ecJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a4l-9200000000-84ceb4ca447a62939b63JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityCarisoprodol 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.
MetabolismHepatic. 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
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the relief of discomfort associated with acute, painful, musculoskeletal conditions.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms 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
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00395
HMDB IDHMDB14539
PubChem Compound ID2576
ChEMBL IDCHEMBL1233
ChemSpider ID2478
KEGG IDC07927
UniProt IDNot Available
OMIM ID
ChEBI ID3419
BioCyc IDNot Available
CTD IDNot Available
Stitch IDCarisoprodol
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCarisoprodol
References
Synthesis Reference

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

MSDSLink
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. [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. [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. [8322081 ]
  4. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available