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 Meprobamate was withdrawn from European and Canadian markets due to its potential to cause physical and psychological dependence.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

-4.63276802E11
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
Marked differences between metalloproteases meprin A and B in substrate and peptide bond specificity.
2001 Apr 20
The fate of neurotization techniques on reinnervation after denervation of the gastrocnemius muscle: an experimental study.
2001 Jul
Accuracy and precision of computer models to predict passage of crude protein and amino acids to the duodenum of lactating cows.
2001 Mar
Focusing on the genetics of hearing: you ain't heard nothin' yet.
2002
Myosin VIIa, harmonin and cadherin 23, three Usher I gene products that cooperate to shape the sensory hair cell bundle.
2002 Dec 16
Mutations in the alternatively spliced exons of USH1C cause non-syndromic recessive deafness.
2002 Jul
Mast cells in the pathogenesis of chronic back pain: a hypothesis.
2002 Jul
The projections of early enteric neurons are influenced by the direction of neural crest cell migration.
2002 Jul 15
Zinc ligands in an astacin family metalloprotease meprin A.
2002 Jul-Aug
Nonsyndromic recessive deafness DFNB18 and Usher syndrome type IC are allelic mutations of USHIC.
2002 Jun
Defective assembly of sarcoglycan complex in patients with beta-sarcoglycan gene mutations. Study of aneural and innervated cultured myotubes.
2002 Jun
The new MATH: homology suggests shared binding surfaces in meprin tetramers and TRAF trimers.
2002 Oct 23
A selective interaction between OS-9 and the carboxyl-terminal tail of meprin beta.
2002 Sep 13
Meprin proteolytic complexes at the cell surface and in extracellular spaces.
2003
Functional analysis of an arthritogenic synovial fibroblast.
2003
Degeneration of the intervertebral disc.
2003
A need for a 'whole-istic functional genomics' approach in complex human diseases: arthritis.
2003
Expression of meprins in health and disease.
2003
Modification of the transcriptomic response to renal ischemia/reperfusion injury by lipoxin analog.
2003 Aug
Mouse models of USH1C and DFNB18: phenotypic and molecular analyses of two new spontaneous mutations of the Ush1c gene.
2003 Dec 1
Human meprin beta: O-linked glycans in the intervening region of the type I membrane protein protect the C-terminal region from proteolytic cleavage and diminish its secretion.
2003 Feb 1
Association between blood carisoprodol:meprobamate concentration ratios and CYP2C19 genotype in carisoprodol-drugged drivers: decreased metabolic capacity in heterozygous CYP2C19*1/CYP2C19*2 subjects?
2003 Jul
The molecular genetics of Usher syndrome.
2003 Jun
MRF4 gene expression in Xenopus embryos and aneural myofibers.
2003 Mar
Usher syndrome type I G (USH1G) is caused by mutations in the gene encoding SANS, a protein that associates with the USH1C protein, harmonin.
2003 Mar 1
Differences in the activation mechanism between the alpha and beta subunits of human meprin.
2003 May
[Adjuvant therapy with parenteral piracetam in alcohol withdrawal delirium].
2003 May 11
Differential distribution of harmonin isoforms and their possible role in Usher-1 protein complexes in mammalian photoreceptor cells.
2003 Nov
Critical amino acids in the active site of meprin metalloproteinases for substrate and peptide bond specificity.
2003 Oct 24
In vivo mucosal delivery of bioactive human interleukin 1 receptor antagonist produced by Streptococcus gordonii.
2003 Sep 17
Morphology of brachial segments in mudpuppy (Necturus maculosus) spinal cord studied with confocal and electron microscopy.
2004 Apr 5
Transport of meprin subunits through the secretory pathway: role of the transmembrane and cytoplasmic domains and oligomerization.
2004 Aug 13
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
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
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
Indigo carmine for the selective endoscopic intervertebral nuclectomy.
2005 Aug
A novel D458V mutation in the SANS PDZ binding motif causes atypical Usher syndrome.
2005 Dec
Meprin metalloprotease expression and regulation in kidney, intestine, urinary tract infections and cancer.
2005 Jun 13
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
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 Wed Jul 05 22:50:56 UTC 2023
Edited
by admin
on Wed Jul 05 22:50:56 UTC 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 Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
DEA NO. 2820
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
WHO-ATC N05CX01
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
WHO-ATC N05BC01
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
NCI_THESAURUS C29756
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
WHO-ATC N05BC51
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
NCI_THESAURUS C264
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
LIVERTOX NBK548721
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
WHO-VATC QN05BC01
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
WHO-VATC QN05BC51
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
Code System Code Type Description
PUBCHEM
4064
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
RXCUI
6760
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M7199
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1389008
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
CAS
57-53-4
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
IUPHAR
7225
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID3023261
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
DRUG BANK
DB00371
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
DRUG CENTRAL
1704
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
LACTMED
Atovaquone and Proquanil
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
SMS_ID
100000092826
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
LACTMED
Meprobamate
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
INN
533
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL979
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
NSC
30418
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
DAILYMED
9I7LNY769Q
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
NCI_THESAURUS
C47603
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
HSDB
3117
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
EVMPD
SUB08757MIG
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
MESH
D008620
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-337-5
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
WIKIPEDIA
MEPROBAMATE
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 2023
PRIMARY
FDA UNII
9I7LNY769Q
Created by admin on Wed Jul 05 22:50:57 UTC 2023 , Edited by admin on Wed Jul 05 22:50:57 UTC 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