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| Name | Meprobamate | ||||||||||||||||||||||||||||||||||||
| Accession Number | DB00371 (APRD01095) | ||||||||||||||||||||||||||||||||||||
| Type | small molecule | ||||||||||||||||||||||||||||||||||||
| Groups | illicit, approved | ||||||||||||||||||||||||||||||||||||
| Description | A carbamate with hypnotic, sedative, and some muscle relaxant properties, although in therapeutic doses reduction of anxiety rather than a direct effect may be responsible for muscle relaxation. Meprobamate has been reported to have anticonvulsant actions against petit mal seizures, but not against grand mal seizures (which may be exacerbated). It is used in the treatment of anxiety disorders, and also for the short-term management of insomnia but has largely been superseded by the benzodiazepines. (From Martindale, The Extra Pharmacopoeia, 30th ed, p603) Meprobamate is a controlled substance in the U.S. |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| CAS number | 57-53-4 | ||||||||||||||||||||||||||||||||||||
| Weight |
Average: 218.2502 Monoisotopic: 218.126657074 |
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| Chemical Formula | C9H18N2O4 | ||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=NPPQSCRMBWNHMW-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||
| InChI |
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)
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| IUPAC Name |
2-[(carbamoyloxy)methyl]-2-methylpentyl carbamate
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| SMILES |
CCCC(C)(COC(N)=O)COC(N)=O
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| Mass Spec | show (10.1 KB) | ||||||||||||||||||||||||||||||||||||
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| Kingdom | Organic | ||||||||||||||||||||||||||||||||||||
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| Pharmacology | |||||||||||||||||||||||||||||||||||||
| Indication | For the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. | ||||||||||||||||||||||||||||||||||||
| 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 It was the best selling minor tranquilizer for a time but has largely been replaced by benzodiazepines.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). However, it is less sedating at effective doses. It is reported to have some anticonvulsant properties against absence seizures, but can 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. | ||||||||||||||||||||||||||||||||||||
| Mechanism of action | Meprobamate's mechanism of action is not known. It has been shown in animal studies to have effects at multiple sites in the central nervous system, including the thalamus and limbic system. Meprobamate binds to GABAA receptors which interrupt neuronal communication in the reticular formation and spinal cord, causing sedation and altered perception of pain. | ||||||||||||||||||||||||||||||||||||
| Absorption | Well absorbed from the gastrointestinal tract. | ||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||
| Protein binding | Not Available | ||||||||||||||||||||||||||||||||||||
| Metabolism |
Hepatic. |
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| Route of elimination | Not Available | ||||||||||||||||||||||||||||||||||||
| Half life | Plasma half-life is about 10 hours. | ||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | ||||||||||||||||||||||||||||||||||||
| Toxicity | Symptoms of overdose include coma, drowsiness, loss of muscle control, severely impaired breathing, shock, sluggishness, and unresponsiveness. Death has been reported with ingestion of as little as 12 g meprobamate and survival with as much as 40 g. | ||||||||||||||||||||||||||||||||||||
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| Pathways | Not Available | ||||||||||||||||||||||||||||||||||||
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| Properties | |||||||||||||||||||||||||||||||||||||
| State | solid | ||||||||||||||||||||||||||||||||||||
| Melting point | 105 oC | ||||||||||||||||||||||||||||||||||||
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| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||
| General Reference | Not Available | ||||||||||||||||||||||||||||||||||||
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| AHFS Codes | Not Available | ||||||||||||||||||||||||||||||||||||
| PDB Entries | Not Available | ||||||||||||||||||||||||||||||||||||
| FDA label | Not Available | ||||||||||||||||||||||||||||||||||||
| MSDS | show (52.6 KB) | ||||||||||||||||||||||||||||||||||||
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| Targets |
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1. Gamma-aminobutyric-acid receptor subunit alpha-1 Pharmacological action: yesActions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P14867  Gene: GABRA1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
2. Gamma-aminobutyric-acid receptor subunit alpha-2 Pharmacological action: yesActions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P47869 Gene: GABRA2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
3. Gamma-aminobutyric-acid receptor subunit alpha-3 Pharmacological action: yesActions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P34903 Gene: GABRA3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
4. Gamma-aminobutyric-acid receptor subunit alpha-4 Pharmacological action: yesActions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P48169 Gene: GABRA4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
5. Gamma-aminobutyric-acid receptor subunit alpha-5 Pharmacological action: yesActions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P31644 Gene: GABRA5 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
6. Gamma-aminobutyric-acid receptor subunit alpha-6 Pharmacological action: yesActions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: Q16445 Gene: GABRA6 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
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| Enzymes |
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Actions: substrate
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine UniProt ID: P33261Gene: CYP2C19 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
Actions: substrate
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms UniProt ID: P05181Gene: CYP2E1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
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| Transporters |
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1. Multidrug resistance protein 1 Actions: inhibitorEnergy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells UniProt ID: P08183Gene: ABCB1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
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| Comments |
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Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:38
This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.