Meprobamate

Identification

Summary

Meprobamate is an anxiolytic drug used for the short-term management of anxiety symptoms.

Brand Names
Equagesic
Generic Name
Meprobamate
DrugBank Accession Number
DB00371
Background

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is used in the treatment of anxiety disorders, and also for the short-term management of insomnia but has largely been superseded by the benzodiazepines.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.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Weight
Average: 218.2502
Monoisotopic: 218.126657074
Chemical Formula
C9H18N2O4
Synonyms
  • Meprobamat
  • Meprobamate
  • Meprobamato
  • Meprobamatum
  • Meprobamic acid
External IDs
  • DEA No. 2820

Pharmacology

Indication

For the management of anxiety disorders or for the short-term relief of the symptoms of anxiety.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAnxiety disorders••••••••••••
Used as adjunct in combination to managePainCombination Product in combination with: Acetylsalicylic acid (DB00945)••••••••••••••••••
Contraindications & Blackbox Warnings
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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 It was the best selling minor tranquilizer for a time but has largely been replaced by benzodiazepines.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) but it is less sedating at effective doses. Meprobamate exhibits some anticonvulsant effects in absence seizures; however, it is reported to potentially 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 fully understood; in animal studies, meprobamate is reported to act at multiple sites in the central nervous system, such as the thalamus and limbic system. It binds to the GABAA receptors, leading to inhibitory effects on the neurons transmitting signals in the reticular formation and spinal cord. Consequently, effects such as sedation and altered perception of pain are observed.

TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGamma-aminobutyric acid receptor subunit alpha-1
agonist
Humans
AGamma-aminobutyric acid receptor subunit alpha-2
agonist
Humans
AGamma-aminobutyric acid receptor subunit alpha-3
agonist
Humans
AGamma-aminobutyric acid receptor subunit alpha-4
agonist
Humans
AGamma-aminobutyric acid receptor subunit alpha-5
agonist
Humans
AGamma-aminobutyric acid receptor subunit alpha-6
agonist
Humans
Absorption

Well absorbed from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Meprobamate undergoes hepatic metabolism.

Route of elimination

Not Available

Half-life

Plasma half-life is about 10 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include coma, drowsiness, loss of muscle control, severely impaired breathing, shock, sluggishness, and unresponsiveness. There have been a case of death resulting from oral ingestion of 12 g of meprobamate. One case study reports the consumption of 40 g of meprobamate resulting in successful survival.

Pathways
PathwayCategory
Capecitabine Action PathwayDrug action
Capecitabine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Meprobamate is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Meprobamate is combined with Acetazolamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Meprobamate is combined with Acetophenazine.
AgomelatineThe risk or severity of CNS depression can be increased when Meprobamate is combined with Agomelatine.
AlfentanilThe risk or severity of CNS depression can be increased when Meprobamate is combined with Alfentanil.
Food Interactions
  • Avoid alcohol.
  • Take with or without food. Food does not significantly affect absorption.

Products

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International/Other Brands
Equanil (Wyeth) / Meprospan / Miltown (Wallace Laboratories)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Equanil Tablets 400mgTablet400 mg / tabOralWyeth Ayerst Canada Inc.1994-12-312000-03-07Canada flag
Meditran 400mgTablet400 mgOralMedic Laboratory LtÉe1959-12-311996-09-09Canada flag
Meprobamate Tab 400mgTablet400 mg / tabOralPro Doc Limitee1959-12-312001-10-15Canada flag
Meprobamate Tab 400mgTablet400 mg / tabOralDuchesnay Inc.1978-12-312001-10-15Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo Meprobamate Tab 400mgTablet400 mg / tabOralApotex Corporation1975-12-312001-10-09Canada flag
MeprobamateTablet200 mg/1OralAvera McKennan Hospital2015-11-032017-05-24US flag
MeprobamateTablet400 mg/1OralAlembic Pharmaceuticals Inc.2016-03-31Not applicableUS flag
MeprobamateTablet200 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2011-05-23Not applicableUS flag
MeprobamateTablet400 mg/1OralActavis Pharma, Inc.1973-05-032014-04-30US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
282 Mep TabMeprobamate (200 mg) + Acetylsalicylic acid (350 mg) + Caffeine citrate (30 mg) + Codeine phosphate (15 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1959-12-311998-08-14Canada flag
EquagesicMeprobamate (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralMikart, Inc.2008-01-15Not applicableUS flag
Equagesic TabletsMeprobamate (200 mg / tab) + Acetylsalicylic acid (250 mg / tab) + Ethoheptazine citrate (75 mg / tab)TabletOralWyeth Ayerst Canada Inc.1995-12-311997-01-14Canada flag

Categories

ATC Codes
N05BC51 — Meprobamate, combinationsN05CX01 — Meprobamate, combinationsN05BC01 — Meprobamate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as carbamate esters. These are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Carbamate esters
Alternative Parents
Organic carbonic acids and derivatives / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9I7LNY769Q
CAS number
57-53-4
InChI Key
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)
IUPAC Name
2-[(carbamoyloxy)methyl]-2-methylpentyl carbamate
SMILES
CCCC(C)(COC(N)=O)COC(N)=O

References

General References
Not Available
Human Metabolome Database
HMDB0014515
KEGG Drug
D00376
PubChem Compound
4064
PubChem Substance
46508142
ChemSpider
3924
RxNav
6760
ChEBI
6761
ChEMBL
CHEMBL979
ZINC
ZINC000001530701
Therapeutic Targets Database
DAP001507
PharmGKB
PA450377
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Meprobamate
MSDS
Download (52.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline llc
  • Medpointe pharmaceuticals medpointe healthcare inc
  • Wyeth ayerst laboratories
  • Ferndale laboratories inc
  • Alra laboratories inc
  • Teva pharmaceuticals usa inc
  • Alembic ltd
  • Barr laboratories inc
  • Elkins sinn div ah robins co inc
  • Heather drug co inc
  • Impax laboratories inc
  • Invagen pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Ivc industries inc dba inverness medical nutritionals group
  • Lannett co inc
  • Lederle laboratories div american cyanamid co
  • Km lee laboratories inc
  • Mallard inc
  • Mk laboratories inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Nexgen pharma inc
  • Parke davis div warner lambert co
  • L perrigo co
  • Pharmavite pharmaceuticals
  • Purepac pharmaceutical co
  • Private formulations inc
  • Roxane laboratories inc
  • Sandoz inc
  • Scherer laboratories inc
  • Solvay pharmaceuticals
  • Stanlabs pharmaceutical co sub simpak corp
  • Tablicaps inc
  • Usl pharma inc
  • Valeant pharmaceuticals international
  • Vangard laboratories inc div midway medical co
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Whiteworth towne paulsen inc
  • Halsey drug co inc
Packagers
  • C.O. Truxton Inc.
  • Calvin Scott and Co. Inc.
  • Dispensing Solutions
  • Doctor Reddys Laboratories Ltd.
  • GlaxoSmithKline Inc.
  • Group Health Cooperative
  • Heritage Pharmaceuticals
  • InvaGen Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Mikart Inc.
  • Nexgen Pharma Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Prescript Pharmaceuticals
  • Qualitest
  • United Research Laboratories Inc.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral
TabletOral400 mg / tab
TabletOral400 mg
TabletOral200 mg/1
TabletOral400 mg/1
TabletOral200 mg
Prices
Unit descriptionCostUnit
Mepron 750 mg/5ml Suspension5.41USD ml
Mepron 750 mg/5 ml suspension4.95USD ml
Meprobamate 200 mg tablet1.42USD tablet
Meprobamate 400 mg tablet0.84USD tablet
Meprozine 50-25 mg capsule0.78USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6649659Yes2003-11-182017-01-10US flag
US4981874No1991-01-012009-08-15US flag
CA2152615No2001-10-162013-12-23Canada flag
CA1336266No1995-07-112012-07-11Canada flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)105 °CPhysProp
water solubility4700 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.70HANSCH,C ET AL. (1995)
logS-1.67ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility2.47 mg/mLALOGPS
logP1.06ALOGPS
logP0.93Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)15.17Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area104.64 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity53.04 m3·mol-1Chemaxon
Polarizability22.65 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9534
Blood Brain Barrier+0.9864
Caco-2 permeable-0.5731
P-glycoprotein substrateNon-substrate0.5282
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.9033
Renal organic cation transporterNon-inhibitor0.945
CYP450 2C9 substrateNon-substrate0.9108
CYP450 2D6 substrateNon-substrate0.8961
CYP450 3A4 substrateNon-substrate0.7032
CYP450 1A2 substrateNon-inhibitor0.8381
CYP450 2C9 inhibitorNon-inhibitor0.8799
CYP450 2D6 inhibitorNon-inhibitor0.8764
CYP450 2C19 inhibitorNon-inhibitor0.8754
CYP450 3A4 inhibitorNon-inhibitor0.8735
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8914
Ames testNon AMES toxic0.8706
CarcinogenicityNon-carcinogens0.7304
BiodegradationNot ready biodegradable0.965
Rat acute toxicity2.4075 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9943
hERG inhibition (predictor II)Non-inhibitor0.9322
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.1 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9300000000-825aaefb8c418b2efba2
GC-MS Spectrum - EI-BGC-MSsplash10-053u-9100000000-d890d15ca6738ce72f60
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-1900000000-8dd8e00d9af9bce5cd26
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052b-9100000000-c21398e92cac7b48f567
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9000000000-dd49a24a00b896129dbb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9000000000-c537c5c82280244f0974
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9000000000-f351c8e0d2b10b45fdc9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9500000000-f7feaaee4fba685b6990
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-9800000000-fa8ad1a8a36879298d9b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-9200000000-dcfbafecc721d1e4e853
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01si-6900000000-9b84d3d294f75dd81774
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-9200000000-277224a4ccc51175905c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-9000000000-606191a51389c5877914
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-153.604831
predicted
DarkChem Lite v0.1.0
[M-H]-153.565731
predicted
DarkChem Lite v0.1.0
[M-H]-152.3863
predicted
DeepCCS 1.0 (2019)
[M+H]+154.885831
predicted
DarkChem Lite v0.1.0
[M+H]+154.057831
predicted
DarkChem Lite v0.1.0
[M+H]+155.60036
predicted
DeepCCS 1.0 (2019)
[M+Na]+153.132431
predicted
DarkChem Lite v0.1.0
[M+Na]+153.151631
predicted
DarkChem Lite v0.1.0
[M+Na]+164.41544
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Rho JM, Donevan SD, Rogawski MA: Barbiturate-like actions of the propanediol dicarbamates felbamate and meprobamate. J Pharmacol Exp Ther. 1997 Mar;280(3):1383-91. [Article]
  2. Gonzalez LA, Gatch MB, Taylor CM, Bell-Horner CL, Forster MJ, Dillon GH: Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. J Pharmacol Exp Ther. 2009 May;329(2):827-37. doi: 10.1124/jpet.109.151142. Epub 2009 Feb 24. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
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.
Gene Name
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Rho JM, Donevan SD, Rogawski MA: Barbiturate-like actions of the propanediol dicarbamates felbamate and meprobamate. J Pharmacol Exp Ther. 1997 Mar;280(3):1383-91. [Article]
  2. Gonzalez LA, Gatch MB, Taylor CM, Bell-Horner CL, Forster MJ, Dillon GH: Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. J Pharmacol Exp Ther. 2009 May;329(2):827-37. doi: 10.1124/jpet.109.151142. Epub 2009 Feb 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
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.
Gene Name
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. Rho JM, Donevan SD, Rogawski MA: Barbiturate-like actions of the propanediol dicarbamates felbamate and meprobamate. J Pharmacol Exp Ther. 1997 Mar;280(3):1383-91. [Article]
  2. Gonzalez LA, Gatch MB, Taylor CM, Bell-Horner CL, Forster MJ, Dillon GH: Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. J Pharmacol Exp Ther. 2009 May;329(2):827-37. doi: 10.1124/jpet.109.151142. Epub 2009 Feb 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
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.
Gene Name
GABRA4
Uniprot ID
P48169
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-4
Molecular Weight
61622.645 Da
References
  1. Rho JM, Donevan SD, Rogawski MA: Barbiturate-like actions of the propanediol dicarbamates felbamate and meprobamate. J Pharmacol Exp Ther. 1997 Mar;280(3):1383-91. [Article]
  2. Gonzalez LA, Gatch MB, Taylor CM, Bell-Horner CL, Forster MJ, Dillon GH: Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. J Pharmacol Exp Ther. 2009 May;329(2):827-37. doi: 10.1124/jpet.109.151142. Epub 2009 Feb 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Transporter activity
Specific Function
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.
Gene Name
GABRA5
Uniprot ID
P31644
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-5
Molecular Weight
52145.645 Da
References
  1. Rho JM, Donevan SD, Rogawski MA: Barbiturate-like actions of the propanediol dicarbamates felbamate and meprobamate. J Pharmacol Exp Ther. 1997 Mar;280(3):1383-91. [Article]
  2. Gonzalez LA, Gatch MB, Taylor CM, Bell-Horner CL, Forster MJ, Dillon GH: Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. J Pharmacol Exp Ther. 2009 May;329(2):827-37. doi: 10.1124/jpet.109.151142. Epub 2009 Feb 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
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.
Gene Name
GABRA6
Uniprot ID
Q16445
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-6
Molecular Weight
51023.69 Da
References
  1. Rho JM, Donevan SD, Rogawski MA: Barbiturate-like actions of the propanediol dicarbamates felbamate and meprobamate. J Pharmacol Exp Ther. 1997 Mar;280(3):1383-91. [Article]
  2. Gonzalez LA, Gatch MB, Taylor CM, Bell-Horner CL, Forster MJ, Dillon GH: Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. J Pharmacol Exp Ther. 2009 May;329(2):827-37. doi: 10.1124/jpet.109.151142. Epub 2009 Feb 24. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:24