Identification

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Name
Carisoprodol
Accession Number
DB00395  (APRD00417)
Type
Small Molecule
Groups
Approved
Description

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].

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CarisoprodolTablet350 mg/1OralVintage Pharmaceuticals, LLC2007-08-022007-08-02Us
SomaTablet250 mg/1OralMEDA Pharmaceuticals2007-09-01Not applicableUs0037 225020180814 13942 8q2csu
SomaTablet350 mg/1OralMEDA Pharmaceuticals1959-07-01Not applicableUs
SomaTablet350 mg/1OralPhysicians Total Care, Inc.1994-10-042008-05-05Us
SomaTablet250 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2007-09-012015-01-01Us
SomaTablet250 mg/1OralRebel Distributors2007-09-01Not applicableUs
SomaTablet250 mg/1OralStat Rx USA2007-09-01Not applicableUs00037 2250 10 nlmimage10 bd1d5efa
Soma Tablets 350mgTablet350 mgOralCarter Horner Corp.1962-12-312003-03-14Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CarisoprodolTablet350 mg/1Oralbryant ranch prepack2010-07-01Not applicableUs
CarisoprodolTablet350 mg/1OralDirectrx2016-04-01Not applicableUs
CarisoprodolTablet350 mg/1OralOrient Pharma Co., Ltd.2015-06-01Not applicableUs
CarisoprodolTablet350 mg/1Oralmedsource pharmaceuticals2007-02-272019-03-31Us
CarisoprodolTablet350 mg/1OralDirectrx2014-01-01Not applicableUs
CarisoprodolTablet350 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-31Not applicableUs
CarisoprodolTablet350 mg/1OralDirectrx2017-02-16Not applicableUs
CarisoprodolTablet350 mg/1OralNorthwind Pharmaceuticals2014-06-01Not applicableUs
CarisoprodolTablet350 mg/1OralREMEDYREPACK INC.2018-09-06Not applicableUs
CarisoprodolTablet350 mg/1OralCarlsbad Technology, Inc.2018-07-17Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CARISOPRODOL and ASPIRINCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralRising Pharmaceuticals2010-01-07Not applicableUs
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralPar Pharmaceutical1989-03-312012-11-30Us
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralApotheca, Inc.2009-10-012011-01-20Us
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralHeritage2011-03-31Not applicableUs
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralActavis Totowa LLC1998-01-012008-06-20Us
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralPhysicians Total Care, Inc.1992-01-142011-06-30Us
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralRebel Distributors2009-10-01Not applicableUs
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralEon Labs, Inc.1996-04-252020-02-29Us
Carisoprodol and AspirinCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1)TabletOralIngenus Pharmaceuticals Nj, Llc2011-06-09Not applicableUs
Carisoprodol, Aspirin and Codeine PhosphateCarisoprodol (200 mg/1) + Acetylsalicylic acid (325 mg/1) + Codeine phosphate hemihydrate (16 mg/1)TabletOralActavis Totowa LLC1999-06-012008-08-20Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
PrazolamineCarisoprodol (350 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Carisoma / Gencari (Genovate) / Genesafe (Genovate) / Hiranin (Hwang's) / Listaflex (Finadiet) / Sanoma / Tensaprin (Newport)
Categories
UNII
21925K482H
CAS number
78-44-4
Weight
Average: 260.33
Monoisotopic: 260.173607266
Chemical Formula
C12H24N2O4
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

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

Associated Conditions
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]. 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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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].

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].

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].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Carisoprodol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Carisoprodol.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Carisoprodol is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Carisoprodol is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Carisoprodol is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Carisoprodol is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Carisoprodol is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Carisoprodol is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbataceptThe metabolism of Carisoprodol can be increased when combined with Abatacept.
AbirateroneThe metabolism of Carisoprodol can be decreased when combined with Abiraterone.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Evidence Level

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

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. [PubMed:15530999]
  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. [PubMed:15276195]
  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. [PubMed:8322081]
  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. [PubMed:18042478]
  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. [PubMed:20419052]
  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. [PubMed:27758843]
  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. [PubMed:8946470]
  8. Reeves RR, Burke RS: Carisoprodol: abuse potential and withdrawal syndrome. Curr Drug Abuse Rev. 2010 Mar;3(1):33-8. [PubMed:20088817]
  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. [PubMed:21884720]
  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. [PubMed:4980885]
  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. [PubMed:16402094]
  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. [PubMed:19908948]
  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]
External Links
Human Metabolome Database
HMDB0014539
KEGG Drug
D00768
KEGG Compound
C07927
PubChem Compound
2576
PubChem Substance
46506377
ChemSpider
2478
ChEBI
3419
ChEMBL
CHEMBL1233
PharmGKB
PA448809
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Carisoprodol
ATC Codes
M03BA02 — CarisoprodolM03BA72 — Carisoprodol, combinations with psycholepticsM03BA52 — Carisoprodol, combinations excl. psycholeptics
FDA label
Download (111 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentBack Pain Lower Back1

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
TabletOral350 mg/1
TabletOral
Kit
TabletOral250 mg/1
Tablet, film coatedOral350 mg/1
TabletOral350 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-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9200000000-7ee2bc67a583d40d99b8
Mass Spectrum (Electron Ionization)MSsplash10-0a4l-9200000000-84ceb4ca447a62939b63
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Carbamic acid ester / Carbonic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Organonitrogen compound / Carbonyl group
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
carbamate ester (CHEBI:3419)

Targets

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. [PubMed:19244096]
  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. [PubMed:20419052]
  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. [PubMed:26872987]
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. [PubMed:19244096]
  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. [PubMed:26872987]
  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. [PubMed:20419052]
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. [PubMed:19244096]
  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. [PubMed:20419052]
  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. [PubMed:28642232]
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. [PubMed:26872987]
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. [PubMed:26872987]
  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. [PubMed:28642232]

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. [PubMed:12835613]
  2. Dean L: Carisoprodol Therapy and CYP2C19 Genotype . [PubMed:28520382]
  3. Carisoprodol FDA label [File]

Drug created on June 13, 2005 07:24 / Updated on April 16, 2019 22:13