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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:50 UTC
HMDB IDHMDB0014539
Secondary Accession Numbers
  • HMDB14539
Metabolite Identification
Common NameCarisoprodol
DescriptionCarisoprodol, also known as soma or isoprotane, 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. It is used as a muscle relaxant in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. Carisoprodol interrupts neuronal communication within the reticular formation and spinal cord, resulting in sedation and alteration in pain perception. A carbamate ester that is the mono-N-isopropyl derivative of meprobamate (which is a significant metabolite). Carisoprodol is a drug. Carisoprodol is an extremely weak acidic (essentially neutral) compound (based on its pKa). Carisoprodol is a potentially toxic compound.
Structure
Data?1582753190
Synonyms
ValueSource
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamateChEBI
(1-Methylethyl)carbamic acid 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl esterChEBI
2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamateChEBI
2-Methyl-2-propyltrimethylene carbamate isopropylcarbamateChEBI
Carbamic acid 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl esterChEBI
CarisoprodolumChEBI
Isopropyl meprobamateChEBI
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamateChEBI
SomaKegg
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acidGenerator
(1-Methylethyl)carbamate 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl esterGenerator
2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acidGenerator
2-Methyl-2-propyltrimethylene carbamic acid isopropylcarbamic acidGenerator
Carbamate 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl esterGenerator
Isopropyl meprobamic acidGenerator
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamic acidGenerator
CarisoprodateHMDB
CarisoprodatumHMDB
IsomeprobamateHMDB
IsoprotaneHMDB
IsoprothaneHMDB
IsopropylmeprobamateHMDB
Mio relaxHMDB
Schein brand OF carisoprodolHMDB
SomalgitHMDB
SoprodolHMDB
VanadomHMDB
Wallace brand 1 OF carisoprodolHMDB
Belmac brand OF carisoprodolHMDB
CarisomaHMDB
Forest brand OF carisoprodolHMDB
GM Pharmaceuticals brand OF carisoprodolHMDB
IsobamateHMDB
Carter horner brand OF carisoprodolHMDB
Wallace brand 2 OF carisoprodolHMDB
Wallace brand 3 OF carisoprodolHMDB
Chemical FormulaC12H24N2O4
Average Molecular Weight260.33
Monoisotopic Molecular Weight260.173607266
IUPAC Name2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
Traditional NameSoma
CAS Registry Number78-44-4
SMILES
CCCC(C)(COC(N)=O)COC(=O)NC(C)C
InChI Identifier
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)
InChI KeyOFZCIYFFPZCNJE-UHFFFAOYSA-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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point92 - 93 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.79 g/LNot Available
LogP2.1Not Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9320000000-ea5623d29b47a08ec316Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-056r-1920000000-df362ad4c912b7d0fb43Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-4910000000-0fe5eef3c39360c36d38Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-9300000000-94d7b1adea0d831c0950Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dj-9100000000-a99d65f53726ca3b6116Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-618eb5a23da29ec51cb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-d2d07fc2a5972fd4e9f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9000000000-007521fa65c254bad2b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-1920000000-df362ad4c912b7d0fb43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-6490000000-046fd220fa245140ddabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9320000000-b08ca9d93b628ea8b4f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-4f09dfa1c188e3251a65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-9010000000-548142f811b5a3632f8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-37215ebd46867ac40f9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-46650c3ec5dedc27b7ecSpectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9200000000-84ceb4ca447a62939b63Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00395 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00395 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00395
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2478
KEGG Compound IDC07927
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarisoprodol
METLIN IDNot Available
PubChem Compound2576
PDB IDNot Available
ChEBI ID3419
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  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. 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 ]

Enzymes

General function:
Involved in monooxygenase 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:
55944.565
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 ]