MEPROBAMATE

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 Search

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
Sources: https://www.drugs.com/monograph/meprobamate.html
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 Meprobamate was withdrawn from European and Canadian markets due to its potential to cause physical and psychological dependence.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9067327	Activator 1447
Equilibrative nucleoside transporter 1 8 Target ID: CHEMBL1997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6128137	Inhibitor 8504		55.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: https://www.drugs.com/pro/meprobamate.html	Primary		Approved 8583	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

C_max

Value	Dose	Analyte	Population
18.4 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7974621	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
1.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	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

AUC

Value	Dose	Co-administered	Analyte	Population
32 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
76% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7974621	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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C19 1119

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C19 1119	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/books/NBK425390/	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 Sources: https://www.ncbi.nlm.nih.gov/books/NBK425390/

Sourcing

Vendor/Aggregator	ID	URL
Achemtek	0104-020240	http://www.achemtek.com/57-53-4
Alsachim	1520	http://www.alsachim.com/product-C2765-glo.bal-view.html
Aurora Fine Chemicals LLC	A17.878.279	http://online.aurorafinechemicals.com/info?ID=A17.878.279
Avantor Inc	75835-930	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
BioSynth	W-105461	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-105461.html
ChemMol	49416390	http://www.chemmol.com/chemmol/49416390.html
Clearsynth	CS-EB-01302	https://www.clearsynth.com/en/CSEB01302.html
Clearsynth	CS-ER-01294	https://www.clearsynth.com/en/CSER01294.html
LGC Standards	LGCAMP0929.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP0929.00-01
LGC Standards	LGCFOR0929.00	https://www.lgcstandards.com/US/en/p/LGCFOR0929.00
LGC Standards	MM0929.00	https://www.lgcstandards.com/US/en/p/MM0929.00
MuseChem	I007956	https://www.musechem.com/product/I007956.html
OChem	8503	http://www.ocheminc.com/index.php?act=psearch&pid=063M428
Sigma-Aldrich	1389008_USP	https://www.sigmaaldrich.com/catalog/product/usp/1389008?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M-039_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/m039?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M0271_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/m0271?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M0400000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/m0400000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M2392_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/m2392?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S534989	http://www.smolecule.com/products/s534989
Synthink Research Chemicals	SA25301	https://synthinkchemicals.com/product/carisoprodol-ep-impurity-d-meprobamate/
THE BioTek	bt-274767	https://www.thebiotek.com/product/inhibitors/bt-274767

PubMed

Title	Date	PubMed
Marked differences between metalloproteases meprin A and B in substrate and peptide bond specificity.	2001 Apr 20	11278902
Internet-based prescription of sildenafil: a 2104-patient series.	2001 Jan-Mar	11720944
Accuracy and precision of computer models to predict passage of crude protein and amino acids to the duodenum of lactating cows.	2001 Mar	11286419
Focusing on the genetics of hearing: you ain't heard nothin' yet.	2002	12093367
Dense innervation in pseudocapsular tissue compared to aneural interface tissue in loose totally replaced hips.	2002 Apr	11950024
Meprin, a brush-border enzyme, plays an important role in hypoxic/ischemic acute renal tubular injury in rats.	2002 Mar	11849450
Impact of in utero exposure to EtOH on corpus callosum development and paw preference in rats: protective effects of silymarin.	2002 Nov 11	12427259
Modification of the transcriptomic response to renal ischemia/reperfusion injury by lipoxin analog.	2003 Aug	12846743
Mouse models of USH1C and DFNB18: phenotypic and molecular analyses of two new spontaneous mutations of the Ush1c gene.	2003 Dec 1	14519688
Association between blood carisoprodol:meprobamate concentration ratios and CYP2C19 genotype in carisoprodol-drugged drivers: decreased metabolic capacity in heterozygous CYP2C191/CYP2C192 subjects?	2003 Jul	12835613
MRF4 gene expression in Xenopus embryos and aneural myofibers.	2003 Mar	12619139
Urinary meprin-alpha: a potential marker of diabetic nephropathy.	2004 Dec	15645700
A novel method for scoring of docked protein complexes using predicted protein-protein binding sites.	2004 Feb	15007163
Human meprin alpha and beta homo-oligomers: cleavage of basement membrane proteins and sensitivity to metalloprotease inhibitors.	2004 Mar 1	14594449
Aneural culture of rat myoblasts for myocardial transplant.	2004 May	15194356
Genetic heterogeneity in Usher syndrome.	2004 Sep 15	15368488
Sequence and structural analysis of BTB domain proteins.	2005	16207353
Knockdown of c-Myc expression by RNAi inhibits MCF-7 breast tumor cells growth in vitro and in vivo.	2005	15743499
Intersubunit and domain interactions of the meprin B metalloproteinase. Disulfide bonds and protein-protein interactions in the MAM and TRAF domains.	2005 Apr 8	15695509
The molecular immunology of mucositis: implications for evidence-based research in alternative and complementary palliative treatments.	2005 Dec	16322806
A novel D458V mutation in the SANS PDZ binding motif causes atypical Usher syndrome.	2005 Dec	16283141
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	16301217
Scaffold protein harmonin (USH1C) provides molecular links between Usher syndrome type 1 and type 2.	2005 Dec 15	16301216
Interactions in the network of Usher syndrome type 1 proteins.	2005 Feb 1	15590703
Gene expression in the brain and kidney of rainbow trout in response to handling stress.	2005 Jan 6	15634361
Meprin metalloprotease expression and regulation in kidney, intestine, urinary tract infections and cancer.	2005 Jun 13	15943977
Photoreceptor expression of the Usher syndrome type 1 protein protocadherin 15 (USH1F) and its interaction with the scaffold protein harmonin (USH1C).	2005 May 12	15928608
BMP-6 inhibits growth of mature human B cells; induction of Smad phosphorylation and upregulation of Id1.	2005 May 9	15877825
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	16300678
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	16303057
Meprin-alpha in chronic diabetic nephropathy: interaction with the renin-angiotensin axis.	2005 Oct	15942051
Usher I syndrome: unravelling the mechanisms that underlie the cohesion of the growing hair bundle in inner ear sensory cells.	2005 Oct 15	16219682
Analysis of prion strains by PrPSc profiling in sporadic Creutzfeldt-Jakob disease.	2006 Feb	16354106
A history of the understanding of cartilage.	2006 Mar	16242354

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 17:54:26 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:26 GMT 2025`
Record UNII	9I7LNY769Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EQUAGESIC COMPONENT MEPROBAMATE

Preferred Name

English

MEPROBAMATE

Official Name

English

MEPRIAM

Brand Name

English

Q-GESIC COMPONENT MEPROBAMATE

Common Name

English

MEPROBAMATE [JAN]

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 [VANDF]

Common Name

English

AMOSENE

Brand Name

English

NSC-30418

Code

English

MEPROSPAN

Brand 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

NEURAMATE

Brand Name

English

MEPROBAMATE CIV

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05CX01