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
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)
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 |
DescriptionSources: https://www.drugs.com/monograph/meprobamate.htmlCurator'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
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 Meprobamate was withdrawn from European and Canadian markets due to its potential to cause physical and psychological dependence.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 |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9067327 |
|||
Target ID: CHEMBL1997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6128137 |
55.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.drugs.com/pro/meprobamate.html |
Primary | MILTOWN Approved UseMeprobamate 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 Date1955 |
Cmax
Value | Dose | Co-administered | 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 |
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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 |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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 Sources: https://www.ncbi.nlm.nih.gov/books/NBK425390/ |
PubMed
Title | Date | PubMed |
---|---|---|
Marked differences between metalloproteases meprin A and B in substrate and peptide bond specificity. | 2001 Apr 20 |
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Internet-based prescription of sildenafil: a 2104-patient series. | 2001 Jan-Mar |
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Accuracy and precision of computer models to predict passage of crude protein and amino acids to the duodenum of lactating cows. | 2001 Mar |
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Focusing on the genetics of hearing: you ain't heard nothin' yet. | 2002 |
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Dense innervation in pseudocapsular tissue compared to aneural interface tissue in loose totally replaced hips. | 2002 Apr |
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Meprin, a brush-border enzyme, plays an important role in hypoxic/ischemic acute renal tubular injury in rats. | 2002 Mar |
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Impact of in utero exposure to EtOH on corpus callosum development and paw preference in rats: protective effects of silymarin. | 2002 Nov 11 |
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Modification of the transcriptomic response to renal ischemia/reperfusion injury by lipoxin analog. | 2003 Aug |
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Mouse models of USH1C and DFNB18: phenotypic and molecular analyses of two new spontaneous mutations of the Ush1c gene. | 2003 Dec 1 |
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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 |
|
MRF4 gene expression in Xenopus embryos and aneural myofibers. | 2003 Mar |
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Urinary meprin-alpha: a potential marker of diabetic nephropathy. | 2004 Dec |
|
A novel method for scoring of docked protein complexes using predicted protein-protein binding sites. | 2004 Feb |
|
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 |
|
Genetic heterogeneity in Usher syndrome. | 2004 Sep 15 |
|
Sequence and structural analysis of BTB domain proteins. | 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 |
|
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 |
|
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 |
|
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
In Vivo Use Guide
Sources: https://www.drugs.com/monograph/meprobamate.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9067327
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
Edited
Mon Mar 31 17:54:26 GMT 2025
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on
Mon Mar 31 17:54:26 GMT 2025
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Record UNII |
9I7LNY769Q
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN05CX01
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DEA NO. |
2820
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WHO-ATC |
N05CX01
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WHO-ATC |
N05BC01
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NCI_THESAURUS |
C29756
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WHO-ATC |
N05BC51
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NCI_THESAURUS |
C264
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LIVERTOX |
NBK548721
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WHO-VATC |
QN05BC01
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WHO-VATC |
QN05BC51
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4064
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6760
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m7199
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1389008
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57-53-4
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7225
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DB00371
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1704
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Atovaquone and Proquanil
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100000092826
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Meprobamate
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533
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CHEMBL979
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30418
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9I7LNY769Q
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C47603
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3117
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SUB08757MIG
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D008620
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200-337-5
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MEPROBAMATE
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