U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H18N2O4
Molecular Weight 218.2502
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPROBAMATE

SMILES

CCCC(C)(COC(N)=O)COC(N)=O

InChI

InChIKey=NPPQSCRMBWNHMW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C9H18N2O4
Molecular Weight 218.2502
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9067327 | https://www.ncbi.nlm.nih.gov/pubmed/6128137 | http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/meprobamate_107/WC500120737.pdf

Meprobamate is a carbamate derivative used as an anxiolytic drug. Meprobamate enhances GABA-A currents, and at higher concentration, exhibits a separate channel-blocking effect that limits the magnitude of GABA(A) receptor potentiation. It is also a potent adenosine reuptake inhibitor (AdoRI), which is most likely responsible for its lesser degree of sedation compared to barbiturates. Meprobamate was withdrawn from European and Canadian markets due to its potential to cause physical and psychological dependence.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
55.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MILTOWN

Approved Use

Meprobamate tablets are indicated for the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually do not require treatment with an anxiolytic. The effectiveness of meprobamate tablets in long-term use, that is, more than 4 months, has not been assessed by systematic clinical studies. The physician should periodically reassess the usefulness of the drug for the individual patient.

Launch Date

1955
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.8 μg/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.5 μg/mL
350 mg single, oral
dose: 350 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
18.4 μM
700 mg single, oral
dose: 700 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
32 μg × h/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
46 μg × h/mL
350 mg single, oral
dose: 350 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.7 h
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.6 h
350 mg single, oral
dose: 350 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
76%
700 mg single, oral
dose: 700 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEPROBAMATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
likely (co-administration study)
Comment: co-administration of CYP2C19 inhibitors, such as omeprazole or fluvoxamine, could result in increased exposure of carisoprodol and decreased exposure of meprobamate
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
THE ACTION OF SODIUM 4-HYDROXYBUTYRATE ON SPINAL REFLEXES.
1964 Apr
Modification of the transcriptomic response to renal ischemia/reperfusion injury by lipoxin analog.
2003 Aug
Receptor protein tyrosine phosphatase mu expression as a marker for endothelial cell heterogeneity; analysis of RPTPmu gene expression using LacZ knock-in mice.
2003 Jun
Mutations in the gamma-actin gene (ACTG1) are associated with dominant progressive deafness (DFNA20/26).
2003 Nov
Critical amino acids in the active site of meprin metalloproteinases for substrate and peptide bond specificity.
2003 Oct 24
Phorbol 12-myristate 13-acetate-induced ectodomain shedding and phosphorylation of the human meprinbeta metalloprotease.
2003 Oct 31
In vivo mucosal delivery of bioactive human interleukin 1 receptor antagonist produced by Streptococcus gordonii.
2003 Sep 17
Deletion of the mouse meprin beta metalloprotease gene diminishes the ability of leukocytes to disseminate through extracellular matrix.
2004 Apr 1
ProMate: a structure based prediction program to identify the location of protein-protein binding sites.
2004 Apr 16
Morphology of brachial segments in mudpuppy (Necturus maculosus) spinal cord studied with confocal and electron microscopy.
2004 Apr 5
Identification of NPM-ALK interacting proteins by tandem mass spectrometry.
2004 Apr 8
Transport of meprin subunits through the secretory pathway: role of the transmembrane and cytoplasmic domains and oligomerization.
2004 Aug 13
Anatomical organization of motoneurons and interneurons in the mudpuppy (Necturus maculosus) brachial spinal cord: the neural substrate for central pattern generation.
2004 Aug-Sep
Urinary meprin-alpha: a potential marker of diabetic nephropathy.
2004 Dec
Kinetics and rhythm of body contractions in the sponge Tethya wilhelma (Porifera: Demospongiae).
2004 Dec
HTLV-1 and -2 envelope SU subdomains and critical determinants in receptor binding.
2004 Dec 2
A novel method for scoring of docked protein complexes using predicted protein-protein binding sites.
2004 Feb
Structure, diversity, and evolution of the 45-bp VNTR in intron 5 of the USH1C gene.
2004 Mar
Human meprin alpha and beta homo-oligomers: cleavage of basement membrane proteins and sensitivity to metalloprotease inhibitors.
2004 Mar 1
Selective disruption of the E-cadherin-catenin system by an algal toxin.
2004 Mar 8
Aneural culture of rat myoblasts for myocardial transplant.
2004 May
Harp (harmonin-interacting, ankyrin repeat-containing protein), a novel protein that interacts with harmonin in epithelial tissues.
2004 Oct
Dietary phosphorus-responsive genes in the intestine, pyloric ceca, and kidney of rainbow trout.
2004 Sep
Genetic heterogeneity in Usher syndrome.
2004 Sep 15
Sequence and structural analysis of BTB domain proteins.
2005
Inhibitors of polyamine biosynthesis decrease the expression of the metalloproteases meprin alpha and MMP-7 in hormone-independent human breast cancer cells.
2005
Metastasis of hormone-independent breast cancer to lung and bone is decreased by alpha-difluoromethylornithine treatment.
2005
Knockdown of c-Myc expression by RNAi inhibits MCF-7 breast tumor cells growth in vitro and in vivo.
2005
Intersubunit and domain interactions of the meprin B metalloproteinase. Disulfide bonds and protein-protein interactions in the MAM and TRAF domains.
2005 Apr 8
Indigo carmine for the selective endoscopic intervertebral nuclectomy.
2005 Aug
[Usher syndrome type I and the differentiation of inner ear sensory cells' hair bundles].
2005 Aug-Sep
The molecular immunology of mucositis: implications for evidence-based research in alternative and complementary palliative treatments.
2005 Dec
A novel D458V mutation in the SANS PDZ binding motif causes atypical Usher syndrome.
2005 Dec
Usherin, the defective protein in Usher syndrome type IIA, is likely to be a component of interstereocilia ankle links in the inner ear sensory cells.
2005 Dec 15
Scaffold protein harmonin (USH1C) provides molecular links between Usher syndrome type 1 and type 2.
2005 Dec 15
Interactions in the network of Usher syndrome type 1 proteins.
2005 Feb 1
Gene expression in the brain and kidney of rainbow trout in response to handling stress.
2005 Jan 6
Meprin metalloprotease expression and regulation in kidney, intestine, urinary tract infections and cancer.
2005 Jun 13
Photoreceptor expression of the Usher syndrome type 1 protein protocadherin 15 (USH1F) and its interaction with the scaffold protein harmonin (USH1C).
2005 May 12
BMP-6 inhibits growth of mature human B cells; induction of Smad phosphorylation and upregulation of Id1.
2005 May 9
Stimulation of poliovirus RNA synthesis and virus maturation in a HeLa cell-free in vitro translation-RNA replication system by viral protein 3CDpro.
2005 Nov 21
Expression and genomic organization of zonadhesin-like genes in three species of fish give insight into the evolutionary history of a mosaic protein.
2005 Nov 22
Neuromuscular synapses can form in vivo by incorporation of initially aneural postsynaptic specializations.
2005 Oct
Meprin beta metalloprotease gene polymorphisms associated with diabetic nephropathy in the Pima Indians.
2005 Oct
Meprin-alpha in chronic diabetic nephropathy: interaction with the renin-angiotensin axis.
2005 Oct
Usher I syndrome: unravelling the mechanisms that underlie the cohesion of the growing hair bundle in inner ear sensory cells.
2005 Oct 15
Mannan-binding protein blocks the activation of metalloproteases meprin alpha and beta.
2005 Sep 1
Generation of biologically active interleukin-1beta by meprin B.
2005 Sep 7
Analysis of prion strains by PrPSc profiling in sporadic Creutzfeldt-Jakob disease.
2006 Feb
A history of the understanding of cartilage.
2006 Mar
Patents

Sample Use Guides

Meprobamate is administered orally. The smallest effective individual doses should be used to avoid oversedation. Typical dose is 1.2–1.6 g daily in 3 or 4 divided doses.
Route of Administration: Oral
In Vitro Use Guide
All electrophysiological recordings were conducted on the stage of a Nikon Diaphot inverted phase contrast microscope at room temperature (23–25°C). Currents were monitored with either an Axopatch 1B or 200A patch clamp amplifier. Voltages corresponding to the currents were acquired with a high-speed chart recorder, and digitized for off-line analysis with the Axotape software package. The holding potential for whole-cell recordings was −60 mV unless otherwise noted. Drugs were dissolved in buffer on the day of use and applied via a nine-barrel rapid perfusion system in which all barrels (320 μm outer diameter quartz tubes; J & W Scientific, Folsom, CA) emptied via a common tip positioned within 200 μm from the tip of the patch electrode in excised patch recordings and 400 μm from the cell under study in whole-cell recordings. Flow through each barrel was gravity fed and regulated by high-speed solenoid microvalves (The Lee Co., Westbrook, CT) operated by a programmable microprocessor-based controller. Switching between solutions occurred within <10 ms (seeDonevan et al., 1992). One barrel contained buffer and the others were filled with various drugs alone and in combination. Only one valve was open at a time, and the buffer solution was applied continuously between drug applications. In the single-channel recordings, drugs were applied for 15- to 60-s epochs, separated by 30- to 60-s wash periods. In whole-cell voltage-clamp recordings from cultured rat hippocampal neurons, meprobamate enhanced GABA-evoked responses in a concentration-dependent manner with EC50 of 1.2 mM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:13 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:13 GMT 2023
Record UNII
9I7LNY769Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEPROBAMATE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official Name English
MEPRIAM
Brand Name English
Q-GESIC COMPONENT MEPROBAMATE
Common Name English
MEPROBAMATE [JAN]
Common Name English
EQUAGESIC COMPONENT MEPROBAMATE
Common Name English
BAMATE
Brand Name English
EQUANIL
Brand Name English
MICRAININ COMPONENT MEPROBAMATE
Common Name English
TRANMEP
Brand Name English
MEPROBAMATE [USP MONOGRAPH]
Common Name English
Meprobamate [WHO-DD]
Common Name English
MEPROBAMATE COMPONENT OF EQUAGESIC
Common Name English
MEPROBAMATE [VANDF]
Common Name English
AMOSENE
Brand Name English
NSC-30418
Code English
MEPROSPAN
Brand Name English
MEPROBAMATE COMPONENT OF Q-GESIC
Common Name English
MEPROBAMATE CIV [USP-RS]
Common Name English
MEPROBAMATE [MI]
Common Name English
MEPROBAMATE [HSDB]
Common Name English
MILTOWN
Brand Name English
MEPROBAMATE [ORANGE BOOK]
Common Name English
2-Methyl-2-propyl-1,3-propanediol dicarbamate
Systematic Name English
1,3-PROPANEDIOL, 2-METHYL-2-PROPYL-, DICARBAMATE
Systematic Name English
meprobamate [INN]
Common Name English
MEPROBAMATE [EP IMPURITY]
Common Name English
MEPROBAMATE [MART.]
Common Name English
MEPRO-ASPIRIN COMPONENT MEPROBAMATE
Common Name English
MEPROBAMATE COMPONENT OF MICRAININ
Common Name English
NEURAMATE
Brand Name English
MEPROBAMATE COMPONENT OF MEPRO-ASPIRIN
Common Name English
MEPROBAMATE CIV
USP-RS  
Common Name English
Classification Tree Code System Code
WHO-VATC QN05CX01
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
DEA NO. 2820
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
WHO-ATC N05CX01
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
WHO-ATC N05BC01
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
WHO-ATC N05BC51
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
NCI_THESAURUS C264
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
LIVERTOX NBK548721
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
WHO-VATC QN05BC01
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
WHO-VATC QN05BC51
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
Code System Code Type Description
PUBCHEM
4064
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
RXCUI
6760
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m7199
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1389008
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
CAS
57-53-4
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
IUPHAR
7225
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID3023261
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
DRUG BANK
DB00371
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
DRUG CENTRAL
1704
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
LACTMED
Atovaquone and Proquanil
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
SMS_ID
100000092826
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
LACTMED
Meprobamate
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
INN
533
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL979
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
NSC
30418
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
DAILYMED
9I7LNY769Q
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
NCI_THESAURUS
C47603
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
HSDB
3117
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
EVMPD
SUB08757MIG
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
MESH
D008620
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-337-5
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
WIKIPEDIA
MEPROBAMATE
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
FDA UNII
9I7LNY769Q
Created by admin on Fri Dec 15 15:20:13 GMT 2023 , Edited by admin on Fri Dec 15 15:20:13 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY