carisoprodol   Click here for help

GtoPdb Ligand ID: 7610

Synonyms: Soma®
Approved drug
carisoprodol is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Carisoprodol is a racemic mixture of enantiomers; R-carisoprodol and S-carisoprodol. We show the non-stereo molecule to represent the mixture.
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 90.65
Molecular weight 260.17
XLogP 2.1
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCC(COC(=O)N)(COC(=O)NC(C)C)C
Isomeric SMILES CCCC(COC(=O)N)(COC(=O)NC(C)C)C
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)
InChI Key OFZCIYFFPZCNJE-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Carisoprodol is a centrally acting skeletal muscle relaxant which is used in combination with rest and physical therapy to treat injuries and other painful musculoskeletal conditions. Carisoprodol is contained in some fixed-mixture formulations with aspirin or codeine and caffeine.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Carisoprodol has significant pharmacological activity, although its clinical benefit is likely due to its meprobamate metabolite, which has superior bioavailability. Carisoprodol also appears to potentiate the activity of hydrocodone, dihydrocodeine, codeine and similar opioid receptor agonists. The precise MMOA of carisoprodol has not been fully resolved, but may involve general central nervous system depression and/or sedative actions.
External links Click here for help
For extended ADME data see the following:

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