Carisoprodol

Identification

Summary

Carisoprodol is a centrally acting muscle relaxant used to relieve the discomfort associated with various musculoskeletal conditions.

Brand Names
Soma, Vanadom
Generic Name
Carisoprodol
DrugBank Accession Number
DB00395
Background

Originally approved by the FDA in 1959 Label, carisoprodol is a centrally acting muscle relaxant used in painful musculoskeletal conditions in conjunction with physical therapy and other medications 4. This drug is available by itself in an oral tablet or combined with aspirin, or in a fixed-dose combination with both aspirin and codeine Label,16,17.

In January 2012, this drug was classified as a Schedule IV substance under the controlled substances act in several US states due to alarming rates of abuse 5,8 despite having a low potential for abuse in addition to a low risk of dependence 13.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 260.33
Monoisotopic: 260.173607266
Chemical Formula
C12H24N2O4
Synonyms
  • (±)-2-methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate
  • (1-methylethyl)carbamic acid 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl ester
  • (RS)-2-{[(aminocarbonyl)oxy]methyl}-2-methylpentyl isopropylcarbamate
  • 2-methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate
  • 2-methyl-2-propyltrimethylene carbamate isopropylcarbamate
  • carbamic acid 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl ester
  • Carisoprodol
  • Carisoprodolo
  • Carisoprodolum
  • Isobamate
  • Isomeprobamate
  • Isopropyl meprobamate
  • Isopropylmeprobamate
  • N-isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamate

Pharmacology

Indication

Carisoprodol is indicated for the relief of discomfort related to acute, painful musculoskeletal conditions Label.

Important limitations of use Label:

• Should only be used for acute treatment periods up to two or three weeks

• Adequate evidence of effectiveness for more prolonged use has not been established

• Not recommended in pediatric patients less than 16 years of age

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAcute pain•••••••••••••••••
Used in combination for symptomatic treatment ofAcute discomfortCombination Product in combination with: Acetylsalicylic acid (DB00945), Codeine (DB00318)•••••••••••••••••
Used in combination for symptomatic treatment ofAcute discomfortCombination Product in combination with: Acetylsalicylic acid (DB00945)•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Carisoprodol is a centrally acting skeletal muscle relaxant that does not act directly on skeletal muscle but acts directly on the central nervous system (CNS). This drug relieves the painful effects of muscle spasm 12,19. A metabolite of carisoprodol, meprobamate, possesses both anxiolytic and sedative properties Label. Clinical studies have shown that this drug causes impairment of psychomotor performance in neuropsychological tests.5,10

Mechanism of action

The mechanism of action of carisoprodol in relieving discomfort associated with acute painful musculoskeletal conditions has not been confirmed. In studies using animal models, the muscle relaxation that is induced by carisoprodol is associated with a change in the interneuronal activity of the spinal cord and of the descending reticular formation, located in the brain.Label

The abuse potential of this drug is attributed to its ability to alter GABAA function.8 This drug has been shown to modulate a variety of GABAA receptor subunits.5,6 GABAA receptor modulation can lead to anxiolysis due to inhibitory effects on neurotransmission.11

TargetActionsOrganism
UGamma-aminobutyric acid receptor subunit alpha-1
activator
modulator
Humans
UGamma-aminobutyric acid receptor subunit beta-2
modulator
Humans
UGamma-aminobutyric acid receptor subunit gamma-2Not AvailableHumans
UGamma-aminobutyric acid receptor subunit alpha-5
modulator
Humans
UGamma-aminobutyric acid receptor subunit alpha-3
modulator
Humans
Absorption

The absolute bioavailability of carisoprodol has not yet been established. The mean time to peak plasma concentrations (Tmax) of this drug was about 1.5-2 hours in clinical studies Label. Co-administration of a fatty meal with carisoprodol (350 mg tablet) had no impact on carisoprodol pharmacokinetics Label.

Volume of distribution

0.93 to 1.3 L/kg, according to 4 different clinical studies 6.

Protein binding

Approximately 60% 14.

Metabolism

The main pathway of carisoprodol is liver metabolism is by the cytochrome enzyme CYP2C19 to form meprobamate. This enzyme exhibits genetic polymorphism, which may affect the metabolism of this drug Label.

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Route of elimination

Carisoprodol is eliminated by the kidneys as well as other routes. The half-life of meprobamate is approximately 10 hours Label.

Half-life

The terminal half-life is approximately 2 hours Label.

Clearance

Following an oral dose of carisoprodol, the oral clearance (Cl/F) was 39.52 ± 16.83 L/hour 15.

Adverse Effects
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Toxicity

LD50 values

The LD50 values of carisoprodol for rats are 450 mg/kg for intravenous (IV) and intraperitoneal injection, and 1,320 mg/kg for gavage dosing. In mice, the LD50 values are 165 mg/kg for intravenous injection, 980 mg/kg for intraperitoneal injection, and 2,340 mg/kg for gavage dosing. The LD50 value for rabbits given carisoprodol by intravenous injection is 124 mg/kg 18.

Overdose

An overdose of carisoprodol leads to CNS depression, and in severe cases, induction of a coma. Shock, depression of respiratory function, seizures and death have also been reported in rare cases. Several symptoms may be associated with carisoprodol overdose, such as horizontal and vertical nystagmus, blurred vision, mydriasis, mild tachycardia and hypotension, respiratory depression, euphoria, CNS stimulation, muscular incoordination, and/or rigidity, confusion, headache, hallucinations, and dystonic reactions. Alcohol or other CNS depressants or psychotropic agents can exert additive effects on carisoprodol even when one of the agents has been ingested at the normal, therapeutic dose. Fatal accidental and non-accidental overdoses have both been reported with carisoprodol ingestion alone or ingestion of carisoprodol in combination with alcohol or psychotropic drugs 15.

A note on dependence and withdrawal

In the postmarketing reports after carisoprodol use, cases of dependence, withdrawal, and abuse have been reported with long-term use. The majority of dependence and withdrawal cases, as well as abuse, have occurred in patients with a history of addiction or who have used this drug in combination with other drugs having abuse potential. However, multiple post-marketing adverse event reports have been made of carisodopril-associated abuse when used without other drugs possessing abuse potential. Withdrawal symptoms have been observed and reported following sudden abrupt cessation after long-term carisodoprol use. To reduce the chance of carisodopril dependence, withdrawal, or abuse, carisodopril should be used with caution in addiction-prone patients and in patients taking other CNS depressants including alcohol. This drug should not be taken for longer than 2 to 3 weeks for symptomatic relief of acute musculoskeletal discomfort Label.

Use in pregnancy

This drug has been classified as Pregnancy Category C. There are no clinical trial data on the use of carisoprodol during human pregnancy. Animal studies show that carisoprodol crosses the placenta and leads to adverse effects on fetal growth and postnatal survival. In postmarketing reports, the main metabolite, meprobamate, has not demonstrated a consistent association between maternal use and an increased risk for specific congenital malformations Label.

Use in nursing

Limited data in humans demonstrate that this is found excreted in breast milk and may reach concentrations in breast milk of 2-4 times the maternal plasma concentrations Label. It is therefore advisable to exercise caution when this drug is used during breastfeeding Label.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer.Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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 adverse effects can be increased when Carisoprodol is combined with 1,2-Benzodiazepine.
AbataceptThe metabolism of Carisoprodol can be increased when combined with Abatacept.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Carisoprodol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Carisoprodol.
AcetazolamideThe risk or severity of adverse effects can be increased when Carisoprodol is combined with Acetazolamide.
Food Interactions
  • Avoid alcohol.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Images
International/Other Brands
Carisoma / Gencari (Genovate) / Genesafe (Genovate) / Hiranin (Hwang's) / Listaflex (Finadiet) / Sanoma / Tensaprin (Newport)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CarisoprodolTablet350 mg/1OralVintage Pharmaceuticals, LLC2007-08-022007-08-02US flag
SomaTablet350 mg/1OralMeda Pharmaceuticals Inc.1995-11-01Not applicableUS flag
SomaTablet250 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2007-09-012015-01-01US flag
SomaTablet250 mg/1OralRebel Distributors2007-09-01Not applicableUS flag
SomaTablet250 mg/1OralMeda Pharmaceuticals Inc.2007-09-08Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CarisoprodolTablet350 mg/1OralAmerincan Health Packaging2009-12-212019-02-28US flag
CarisoprodolTablet350 mg/1Oralbryant ranch prepack2019-08-08Not applicableUS flag
CarisoprodolTablet350 mg/1OralA-S Medication Solutions2010-07-01Not applicableUS flag
CarisoprodolTablet350 mg/1OralAv Kare, Inc.2011-09-262015-02-20US flag
CarisoprodolTablet350 mg/1OralNostrum Laboratories, Inc.2021-10-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralPar Pharmaceutical1989-03-312012-11-30US flag
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralIngenus Pharmaceuticals Nj, Llc2011-06-092011-06-09US flag
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralEon Labs, Inc.1996-04-252020-02-29US flag
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralActavis Totowa LLC1998-01-012008-06-20US flag
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralPhysicians Total Care, Inc.1992-01-142011-06-30US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
PrazolamineCarisoprodol (350 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag

Categories

ATC Codes
M03BA02 — CarisoprodolM03BA72 — Carisoprodol, combinations with psycholepticsM03BA52 — Carisoprodol, combinations excl. psycholeptics
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
carbamate ester (CHEBI:3419)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
21925K482H
CAS number
78-44-4
InChI Key
OFZCIYFFPZCNJE-UHFFFAOYSA-N
InChI
InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
IUPAC Name
2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
SMILES
CCCC(C)(COC(N)=O)COC(=O)NC(C)C

References

Synthesis Reference

Berger, F.M. and Ludwig, B.J.; U S . Patent 2,937,119; May 17,1960; assigned to Carter Products, Inc.

General References
  1. Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. [Article]
  2. Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. [Article]
  3. Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6. [Article]
  4. Owens C, Pugmire B, Salness T, Culbertson V, Force R, Cady P, Steiner J: Abuse potential of carisoprodol: a retrospective review of Idaho Medicaid pharmacy and medical claims data. Clin Ther. 2007 Oct;29(10):2222-5. doi: 10.1016/j.clinthera.2007.10.003. [Article]
  5. Gonzalez LA, Gatch MB, Forster MJ, Dillon GH: Abuse Potential of Soma: the GABA(A) Receptor as a Target. Mol Cell Pharmacol. 2009 Jan 1;1(4):180-186. [Article]
  6. Lewandowski TA: Pharmacokinetic modeling of carisoprodol and meprobamate disposition in adults. Hum Exp Toxicol. 2017 Aug;36(8):846-853. doi: 10.1177/0960327116672912. Epub 2016 Oct 10. [Article]
  7. Dalen P, Alvan G, Wakelkamp M, Olsen H: Formation of meprobamate from carisoprodol is catalysed by CYP2C19. Pharmacogenetics. 1996 Oct;6(5):387-94. [Article]
  8. Reeves RR, Burke RS: Carisoprodol: abuse potential and withdrawal syndrome. Curr Drug Abuse Rev. 2010 Mar;3(1):33-8. [Article]
  9. Zacny JP, Paice JA, Coalson DW: Characterizing the subjective and psychomotor effects of carisoprodol in healthy volunteers. Pharmacol Biochem Behav. 2011 Nov;100(1):138-43. doi: 10.1016/j.pbb.2011.08.011. Epub 2011 Aug 23. [Article]
  10. Raffel SC, Swink R, Lampton TD: The influence of chlorphenesin carbamate and carisoprodol on psychological test scores. Curr Ther Res Clin Exp. 1969 Sep;11(9):553-60. [Article]
  11. Bowery NG, Smart TG: GABA and glycine as neurotransmitters: a brief history. Br J Pharmacol. 2006 Jan;147 Suppl 1:S109-19. doi: 10.1038/sj.bjp.0706443. [Article]
  12. Serfer GT, Wheeler WJ, Sacks HJ: Randomized, double-blind trial of carisoprodol 250 mg compared with placebo and carisoprodol 350 mg for the treatment of low back spasm. Curr Med Res Opin. 2010 Jan;26(1):91-9. doi: 10.1185/03007990903382428. [Article]
  13. Drug Scheduling: United States Drug Enforcement Administration (DEA) [Link]
  14. Muscle relaxants for lower back pain: What is the evidence (article, Journal of Pain Management) [Link]
  15. Carisoprodol Monograph [File]
  16. Carisoprodol-Aspirin compound [File]
  17. Soma compound with codeine [File]
  18. Toxicity studies of carisoprodol: National Toxicology Program [File]
  19. Skeletal muscle relaxants therapeutic class review [File]
Human Metabolome Database
HMDB0014539
KEGG Drug
D00768
KEGG Compound
C07927
PubChem Compound
2576
PubChem Substance
46506377
ChemSpider
2478
RxNav
2101
ChEBI
3419
ChEMBL
CHEMBL1233
PharmGKB
PA448809
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Carisoprodol
FDA label
Download (111 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentBack Pain Lower Back2

Pharmacoeconomics

Manufacturers
  • Meda pharmaceuticals meda pharmaceuticals inc
  • Able laboratories inc
  • Actavis totowa llc
  • Advent pharmaceuticals inc
  • Aurobindo pharma ltd
  • Concord laboratories inc
  • Corepharma llc
  • Mutual pharmaceutical co inc
  • Pioneer pharmaceuticals inc
  • Sandoz inc
  • Sun pharmaceutical industries ltd
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Schering corp sub schering plough corp
Packagers
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Chattem Chemicals Inc.
  • Corepharma LLC
  • Darby Dental Supply Co. Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • Eon Labs
  • Gm Pharmaceuticals Inc.
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Meda AB
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Vintage Pharmaceuticals Inc.
  • Vision Pharma LLC
  • Wallace Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
CapsuleOral
TabletOral350 mg/1
TabletOral
KitOral
TabletOral250 mg/1
Tablet, film coatedOral350 mg/1
TabletOral350 mg
TabletOral350.000 mg
Prices
Unit descriptionCostUnit
Soma 350 mg tablet5.75USD tablet
Soma Compound 200-325 mg tablet4.58USD tablet
Soma 250 mg tablet3.24USD tablet
Carisoprodol powder1.17USD g
Carisoprodol 350 mg tablet0.57USD tablet
Flexall plus gel0.08USD g
Flexall 16% gel0.06USD g
Flexall 7% gel0.05USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)92https://www.lookchem.com/Carisoprodol/
boiling point (°C)423.412https://www.lookchem.com/Carisoprodol/
water solubilityslightly solublehttps://www.lookchem.com/Carisoprodol/
logP2.1http://www.t3db.ca/toxins/T3D3491
logS-2.5http://www.t3db.ca/toxins/T3D3491
pKa15.06 (Strongest acidic)http://www.t3db.ca/toxins/T3D3491
Predicted Properties
PropertyValueSource
Water Solubility0.792 mg/mLALOGPS
logP1.76ALOGPS
logP1.92Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.06Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area90.65 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity67.1 m3·mol-1Chemaxon
Polarizability28.77 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9626
Blood Brain Barrier+0.9679
Caco-2 permeable-0.5533
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8014
P-glycoprotein inhibitor IINon-inhibitor0.8381
Renal organic cation transporterNon-inhibitor0.9519
CYP450 2C9 substrateNon-substrate0.9041
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6418
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8659
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6872
BiodegradationNot ready biodegradable0.973
Rat acute toxicity2.3261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9957
hERG inhibition (predictor II)Non-inhibitor0.9362
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-052f-9320000000-ea5623d29b47a08ec316
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9200000000-7ee2bc67a583d40d99b8
Mass Spectrum (Electron Ionization)MSsplash10-0a4l-9200000000-84ceb4ca447a62939b63
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-056r-1920000000-df362ad4c912b7d0fb43
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-4910000000-0fe5eef3c39360c36d38
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ot-9300000000-94d7b1adea0d831c0950
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03dj-9100000000-a99d65f53726ca3b6116
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-9000000000-618eb5a23da29ec51cb6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-9000000000-d2d07fc2a5972fd4e9f8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-9000000000-007521fa65c254bad2b6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056r-1920000000-df362ad4c912b7d0fb43
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9830000000-3dd981b3efaff494639c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-2920000000-ef57df518334f5b6f90d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f7k-9510000000-62b33e836bd962bf1d2a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0036-4900000000-20aaf5362d054b584dd9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-9300000000-aa7c34cc4e2228c77400
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0016-9000000000-64ab3f36957ea1f52a7d
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]-169.3233515
predicted
DarkChem Lite v0.1.0
[M-H]-163.79927
predicted
DeepCCS 1.0 (2019)
[M+H]+170.7737515
predicted
DarkChem Lite v0.1.0
[M+H]+166.15726
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.1262515
predicted
DarkChem Lite v0.1.0
[M+Na]+172.25041
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
Modulator
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. 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]
  2. Gonzalez LA, Gatch MB, Forster MJ, Dillon GH: Abuse Potential of Soma: the GABA(A) Receptor as a Target. Mol Cell Pharmacol. 2009 Jan 1;1(4):180-186. [Article]
  3. Kumar M, Dillon GH: Assessment of direct gating and allosteric modulatory effects of meprobamate in recombinant GABA(A) receptors. Eur J Pharmacol. 2016 Mar 15;775:149-58. doi: 10.1016/j.ejphar.2016.02.031. Epub 2016 Feb 9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
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
GABRB2
Uniprot ID
P47870
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-2
Molecular Weight
59149.895 Da
References
  1. 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]
  2. Kumar M, Dillon GH: Assessment of direct gating and allosteric modulatory effects of meprobamate in recombinant GABA(A) receptors. Eur J Pharmacol. 2016 Mar 15;775:149-58. doi: 10.1016/j.ejphar.2016.02.031. Epub 2016 Feb 9. [Article]
  3. Gonzalez LA, Gatch MB, Forster MJ, Dillon GH: Abuse Potential of Soma: the GABA(A) Receptor as a Target. Mol Cell Pharmacol. 2009 Jan 1;1(4):180-186. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
GABRG2
Uniprot ID
P18507
Uniprot Name
Gamma-aminobutyric acid receptor subunit gamma-2
Molecular Weight
54161.78 Da
References
  1. 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]
  2. Gonzalez LA, Gatch MB, Forster MJ, Dillon GH: Abuse Potential of Soma: the GABA(A) Receptor as a Target. Mol Cell Pharmacol. 2009 Jan 1;1(4):180-186. [Article]
  3. Kumar M, Kumar M, Freund JM, Dillon GH: A Single Amino Acid Residue at Transmembrane Domain 4 of the alpha Subunit Influences Carisoprodol Direct Gating Efficacy at GABAA Receptors. J Pharmacol Exp Ther. 2017 Sep;362(3):395-404. doi: 10.1124/jpet.117.242156. Epub 2017 Jun 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
Curator comments
Data regarding this target action are based on the results of in vitro studies, and information regarding this action is limited in the literature.
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. Kumar M, Dillon GH: Assessment of direct gating and allosteric modulatory effects of meprobamate in recombinant GABA(A) receptors. Eur J Pharmacol. 2016 Mar 15;775:149-58. doi: 10.1016/j.ejphar.2016.02.031. Epub 2016 Feb 9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
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. Kumar M, Dillon GH: Assessment of direct gating and allosteric modulatory effects of meprobamate in recombinant GABA(A) receptors. Eur J Pharmacol. 2016 Mar 15;775:149-58. doi: 10.1016/j.ejphar.2016.02.031. Epub 2016 Feb 9. [Article]
  2. Kumar M, Kumar M, Freund JM, Dillon GH: A Single Amino Acid Residue at Transmembrane Domain 4 of the alpha Subunit Influences Carisoprodol Direct Gating Efficacy at GABAA Receptors. J Pharmacol Exp Ther. 2017 Sep;362(3):395-404. doi: 10.1124/jpet.117.242156. Epub 2017 Jun 22. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Bramness JG, Skurtveit S, Fauske L, Grung M, Molven A, Morland J, Steen VM: Association between blood carisoprodol:meprobamate concentration ratios and CYP2C19 genotype in carisoprodol-drugged drivers: decreased metabolic capacity in heterozygous CYP2C19*1/CYP2C19*2 subjects? Pharmacogenetics. 2003 Jul;13(7):383-8. doi: 10.1097/01.fpc.0000054098.48725.88. [Article]
  2. Dean L: Carisoprodol Therapy and CYP2C19 Genotype . [Article]
  3. Carisoprodol FDA label [File]

Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:41