Human Metabolome Database: Showing metabocard for Carisoprodol (HMDB0014539)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2020-02-26 21:39:50 UTC

HMDB ID

HMDB0014539

Secondary Accession Numbers

HMDB14539

Metabolite Identification

Common Name

Carisoprodol

Description

Carisoprodol, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate	ChEBI
(1-Methylethyl)carbamic acid 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl ester	ChEBI
2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate	ChEBI
2-Methyl-2-propyltrimethylene carbamate isopropylcarbamate	ChEBI
Carbamic acid 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl ester	ChEBI
Carisoprodolum	ChEBI
Isopropyl meprobamate	ChEBI
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamate	ChEBI
Soma	Kegg
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acid	Generator
(1-Methylethyl)carbamate 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl ester	Generator
2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acid	Generator
2-Methyl-2-propyltrimethylene carbamic acid isopropylcarbamic acid	Generator
Carbamate 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl ester	Generator
Isopropyl meprobamic acid	Generator
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamic acid	Generator
Carisoprodate	HMDB
Carisoprodatum	HMDB
Isomeprobamate	HMDB
Isoprotane	HMDB
Isoprothane	HMDB
Isopropylmeprobamate	HMDB
Mio relax	HMDB
Schein brand OF carisoprodol	HMDB
Somalgit	HMDB
Soprodol	HMDB
Vanadom	HMDB
Wallace brand 1 OF carisoprodol	HMDB
Belmac brand OF carisoprodol	HMDB
Carisoma	HMDB
Forest brand OF carisoprodol	HMDB
GM Pharmaceuticals brand OF carisoprodol	HMDB
Isobamate	HMDB
Carter horner brand OF carisoprodol	HMDB
Wallace brand 2 OF carisoprodol	HMDB
Wallace brand 3 OF carisoprodol	HMDB

Chemical Formula

C₁₂H₂₄N₂O₄

Average Molecular Weight

260.33

Monoisotopic Molecular Weight

260.173607266

IUPAC Name

2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate

Traditional Name

Soma

CAS Registry Number

78-44-4

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 Key

OFZCIYFFPZCNJE-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Carbamate 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 Framework

Aliphatic acyclic compounds

External Descriptors

carbamate ester (CHEBI:3419 )

Ontology

Physiological effect

Health effect:

Health condition:

Dizziness

Vascular disorders:

Hypotension

Skin and subcutaneous tissue disorders:

Erythema

Nervous system disorders:

Headache

Gastrointestinal disorders:

Nausea

Psychiatric disorders:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Neuromuscular agent:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	92 - 93 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.79 g/L	Not Available
LogP	2.1	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	1.76	ALOGPS
logP	1.92	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.65 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	67.1 m³·mol⁻¹	ChemAxon
Polarizability	28.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9200000000-7ee2bc67a583d40d99b8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9200000000-7ee2bc67a583d40d99b8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9320000000-ea5623d29b47a08ec316	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-056r-1920000000-df362ad4c912b7d0fb43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-4910000000-0fe5eef3c39360c36d38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01ot-9300000000-94d7b1adea0d831c0950	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03dj-9100000000-a99d65f53726ca3b6116	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-9000000000-618eb5a23da29ec51cb6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-9000000000-d2d07fc2a5972fd4e9f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-9000000000-007521fa65c254bad2b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-056r-1920000000-df362ad4c912b7d0fb43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-6490000000-046fd220fa245140ddab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9320000000-b08ca9d93b628ea8b4f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-4f09dfa1c188e3251a65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000x-9010000000-548142f811b5a3632f8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-37215ebd46867ac40f9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-46650c3ec5dedc27b7ec	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9200000000-84ceb4ca447a62939b63	Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00395	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00395	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00395

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2478

KEGG Compound ID

C07927

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carisoprodol

METLIN ID

Not Available

PubChem Compound

2576

PDB ID

Not Available

ChEBI ID

3419

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]
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

Enzyme Details

1. Cytochrome P450 2C19

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

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 ]

Showing metabocard for Carisoprodol (HMDB0014539)

Structure for HMDB0014539 (Carisoprodol)

Enzymes

References