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 Use of meprobamate has largely been replaced by the benzodiazepines due to their wider therapeutic index and lower incidence of serious side-effects.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: meprobamate

2D Structure
Click here for help

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.

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

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
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
SMILES / InChI / InChIKey
Click here for help

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.

✖
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
No information available.
Summary of Clinical Use Click here for help
Meprobamate is anxiolytic drug used to treat the symptoms of anxiety and related conditions. However, in 2012 the European Medicines Agency recommended withdrawal of all EU marketing authorisations for meprobamate containing drugs, due to severe adverse effects.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Meprobamate can positively modulate the activity of GABAA anion channels. The drug increases inhibitory GABAergic tone and causes neuro-inhibition. Drug-induced effects are observed clinically as anxiolytic and sedative actions and may also contribute towards the suggested anticonvulsant and skeletal muscle relaxant actions of the drug.
Due to the complex and varied nature of the precise subunit composition of GABAA receptors, and a paucity of affinity data with definitive molecular details, we have not tagged a primary target for this drug.
External links Click here for help
For extended ADME data see the following:

Drugs.com
European Medicines Agency (EMA)