General
Preferred name
MEPROBAMATE
Synonyms
Meprobamate (Schedule Iv) ()
Tenavoid ()
Neuramate ()
Mepriam ()
Meprobamato ()
Miltown ()
NSC-30418 ()
Amosene ()
Bamate ()
Meprospan ()
Equanil ()
Tranmep ()
Meprobamate civ ()
Meprobamate-d7 ()
P&D ID
PD010221
CAS
57-53-4
1435933-83-7
Tags
available
drug
Approved by
FDA
First approval
1955
Drug indication
Malaria
Sedative-Hypnotic
Ischemic reperfusion injury
Anxiety disorder
Drug Status
approved
withdrawn
illicit
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION 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 Use of meprobamate has largely been replaced by the benzodiazepines due to their wider therapeutic index and lower incidence of serious side-effects. (GtoPdb)
METABOLISM Meprobamate undergoes hepatic metabolism.
TOXICITY Symptoms of overdose include coma, drowsiness, loss of muscle control, severely impaired breathing, shock, sluggishness, and unresponsiveness. There have been a case of death resulting from oral ingestion of 12 g of meprobamate. One case study reports the consumption of 40 g of meprobamate resulting in successful survival.
MOA Meprobamate's mechanism of action is not fully understood; in animal studies, meprobamate is reported to act at multiple sites in the central nervous system, such as the thalamus and limbic system. It binds to the GABAA receptors, leading to inhibitory effects on the neurons transmitting signals in the reticular formation and spinal cord. Consequently, effects such as sedation and altered perception of pain are observed.
PHARMACODYNAMICS Meprobamate is an anxiolytic drug. It was the best selling minor tranquilizer for a time but has largely been replaced by benzodiazepines. Meprobamate has most of the pharmacological effects and dangers of the barbiturates (though it was marketed as being safer) but it is less sedating at effective doses. Meprobamate exhibits some anticonvulsant effects in absence seizures; however, it is reported to potentially exacerbate generalized tonic-clonic seizures. It has also been used as a hypnotic (sleeping pill). However, its is currently only licensed as an anxiolytic and it is a third or fourth-order choice.
Compound Sets
15
Cayman Chemical Bioactives
15894
18059
ChEMBL Approved Drugs
CHEMBL979
ChEMBL Drugs
CHEMBL979
DrugBank
DB00371
DrugBank Approved Drugs
DB00371
DrugCentral
1704
DrugCentral Approved Drugs
1704
DrugMAP
DMHM93Y
DrugMAP Approved Drugs
DMHM93Y
DrugMatrix
Guide to Pharmacology
7225
NCATS Inxight Approved Drugs
9I7LNY769Q
NPC Screening Collection
ReFrame library
Withdrawn 2.0
DB00371
External IDs
25
Properties
(calculated by RDKit )
Molecular Weight
218.13
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
2
Rotatable Bonds
6
Ring Count
0
Aromatic Ring Count
0
cLogP
0.98
TPSA
104.64
Fraction CSP3
0.78
Chiral centers
0.0
Largest ring
0.0
QED
0.69
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
ATC
N05BC51
N05CX01
N05BC01
Toxicity type
NULL
Therapeutic Class
Antianxiety Agents
Source data