meprobamate   Click here for help

GtoPdb Ligand ID: 7225

Synonyms: Equanil® | Meprospan® | Miltown®
Approved drug
meprobamate is an approved drug (FDA (1955))
Compound class: Synthetic organic
Comment: Meprobamate is a carbamate derivative anxiolytic drug. Use of meprobamate has largely been replaced by the benzodiazepines due to their wider therapeutic index and lower incidence of serious side-effects.
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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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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 4
Rotatable bonds 8
Topological polar surface area 106.62
Molecular weight 218.13
XLogP 2.97
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(=N)O)(COC(=N)O)C
Isomeric SMILES CCCC(COC(=N)O)(COC(=N)O)C
InChI InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)
InChI Key NPPQSCRMBWNHMW-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1955))
Prodrug carisoprodol
IUPAC Name Click here for help
({2-[(C-hydroxycarbonimidoyloxy)methyl]-2-methylpentyl}oxy)carboximidic acid
International Nonproprietary Names Click here for help
INN number INN
533 meprobamate
Synonyms Click here for help
Equanil® | Meprospan® | Miltown®
Database Links Click here for help
CAS Registry No. 57-53-4
ChEMBL Ligand CHEMBL979
DrugBank Ligand DB00371
DrugCentral Ligand 1704
GtoPdb PubChem SID 178103799
PubChem CID 4064
Search Google for chemical match using the InChIKey NPPQSCRMBWNHMW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NPPQSCRMBWNHMW
Search PubMed clinical trials meprobamate
Search PubMed titles meprobamate
Search PubMed titles/abstracts meprobamate
UniChem Compound Search for chemical match using the InChIKey NPPQSCRMBWNHMW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NPPQSCRMBWNHMW-UHFFFAOYSA-N
Wikipedia Meprobamate