CARISOPRODOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H24N2O4
Molecular Weight	260.33
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC(C)(COC(N)=O)COC(=O)NC(C)C

InChI

InChIKey=OFZCIYFFPZCNJE-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/011792s045lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.ncbi.nlm.nih.gov/pubmed/22318620, http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7c9184c0-7a2e-11df-8c8d-0002a5d5c51b

A centrally acting skeletal muscle relaxant whose mechanism of action is not completely understood but may be related to its sedative actions. Carisoprodol is indicated for the relief of discomfort associated with acute, painful musculoskeletal conditions in adults. Most common adverse reactions (incidence > 2%) are drowsiness, dizziness, and headache. Carisoprodol might be mixtured with Aspirin and Codeine Phosphate. Studies indicating increased risk of abuse or addiction led to withdrawal of the drug from the market in Norway and other EU countries in 2008.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor 3 Target ID: CHEMBL2364024 Sources: http://www.ncbi.nlm.nih.gov/pubmed/20419052	Positive Allosteric Modulator 186		142.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Painful musculoskeletal conditions 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/011792s045lbl.pdf	Palliative		Approved 8583	SOMA Approved Use SOMA is indicated for the relief of discomfort associated with acute, painful musculoskeletal conditions in adults. SOMA should only be used for short periods (up to two or three weeks) because adequate evidence of effectiveness for more prolonged use has not been established and because acute, painful musculoskeletal conditions are generally of short duration Launch Date 1959

C_max

Value	Dose	Analyte	Population
13.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7974621	700 mg single, oral dose: 700 mg route of administration: Oral experiment type: SINGLE co-administered:	CARISOPRODOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.2 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CARISOPRODOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/011792s050lbl.pdf	350 mg single, oral dose: 350 mg route of administration: Oral experiment type: SINGLE co-administered:	CARISOPRODOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4.5 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CARISOPRODOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/011792s050lbl.pdf	350 mg single, oral dose: 350 mg route of administration: Oral experiment type: SINGLE co-administered:		CARISOPRODOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
99 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7974621	700 mg single, oral dose: 700 mg route of administration: Oral experiment type: SINGLE co-administered:	CARISOPRODOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011792s048lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CARISOPRODOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/011792s050lbl.pdf	350 mg single, oral dose: 350 mg route of administration: Oral experiment type: SINGLE co-administered:	CARISOPRODOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
46% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7974621	700 mg single, oral dose: 700 mg route of administration: Oral experiment type: SINGLE co-administered:		CARISOPRODOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
250 mg 3 times / day steady, oral Recommended Dose: 250 mg, 3 times / day Route: oral Route: steady Dose: 250 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf	unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf	Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.5%) Headache (0.5%) Diarrhea (0.2%) Stomach discomfort (0.2%) Upper abdominal pain (0.2%) Intervertebral disc protrusion (0.2%) Pain in extremity (0.2%) Abdominal distension (0.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf
350 mg 3 times / day steady, oral Recommended Dose: 350 mg, 3 times / day Route: oral Route: steady Dose: 350 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf	unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf	Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.7%) Headache (0.4%) Stomach discomfort (0.7%) Upper abdominal pain (0.7%) Somnolence (0.7%) Nausea (0.4%) Rash (0.4%) Nephrolithiasis (0.4%) Intervertebral disc protrusion (0.4%) Fatigue (0.4%) Disorientation (0.4%) Paraesthesia (0.4%) Skin papilloma (0.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf
2100 mg 1 times / day steady, oral Highest studied dose Dose: 2100 mg, 1 times / day Route: oral Route: steady Dose: 2100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1998178	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1998178	Sources: https://pubmed.ncbi.nlm.nih.gov/1998178

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946		inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057	CYP2C19 1119 CYP1A2 1197

Drug as perpetrator

Target	Modality	Activity
CYP2C8 1117	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak
CYP2D6 2546	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak
CYP3A4 2633	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak

Drug as victim

Target	Modality	Activity
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/011792s050lbl.pdf Page: 4.0	major
CYP1A2 1197	substrate 4014 Sources: https://link.springer.com/article/10.1007/s40262-016-0373-8 Page: 1012.0	yes
CYP2D6 1388	substrate 4014 Sources: https://link.springer.com/article/10.1007/s40262-016-0373-8 Page: 1012.0	yes
CYP3A4 1946	substrate 4014 Sources: https://link.springer.com/article/10.1007/s40262-016-0373-8 Page: 1012.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3419	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3419
ChemicalBook	CB0215440	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0215440
eMolecules	536553	https://www.emolecules.com/cgi-bin/more?vid=536553

PubMed

Title	Date	PubMed
WHO Expert Committee on Drug Dependence. Thirty-second report.	2001	11851193
Abuse of combinations of carisoprodol and tramadol.	2001 May	11372804
[Guidelines concerning acute low back pain].	2002 Apr 30	12043062
Urticaria to carisoprodol.	2002 Jan	11991293
[Carisoprodol--one more time].	2002 Jan 30	11894608
Carisoprodol: an unrecognized drug of abuse.	2002 Mar	11888078
Somatic dysfunction during carisoprodol cessation: evidence for a carisoprodol withdrawal syndrome.	2003 Feb	12622352
Association between blood carisoprodol:meprobamate concentration ratios and CYP2C19 genotype in carisoprodol-drugged drivers: decreased metabolic capacity in heterozygous CYP2C191/CYP2C192 subjects?	2003 Jul	12835613
Possible dangerous interaction of oxycontin and carisoprodol.	2003 Jun 1	12800958
Possible dangerous interaction of oxycontin and carisoprodol.	2003 Mar 1	12643355
A near-fatal overdose of carisoprodol (SOMA): case report.	2004	15214630
Tolerance and dependence risk with the use of carisoprodol.	2004 Apr 1	15086035
Validated semiquantitative/quantitative screening of 51 drugs in whole blood as silylated derivatives by gas chromatography-selected ion monitoring mass spectrometry and gas chromatography electron capture detection.	2004 Jul 5	15171931
Fatal intoxications in a Swedish forensic autopsy material during 1992-2002.	2004 Jun 30	15177630
Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone.	2004 Sep	15530999
The CYP2C19 genotype and the use of oral contraceptives influence the pharmacokinetics of carisoprodol in healthy human subjects.	2005 Aug	16021435
Human pharmaceuticals, hormones, and personal care product ingredients in runoff from agricultural fields irrigated with treated wastewater.	2005 Mar 9	15740050
Treatment of carisoprodol dependence: a case report.	2005 Sep	16184075
Carisoprodol abuse in Texas, 1998-2003.	2006 Mar	18072105
Carisoprodol abuse in Mississippi.	2007 Dec	19292137
Is the frequency of carisoprodol withdrawal syndrome increasing?	2007 Oct	17896902
Acute intoxications with carisoprodol.	2008 Apr	18363125
Reliability of Ashworth and Modified Ashworth scales in children with spastic cerebral palsy.	2008 Apr 10	18402701
Is it time for carisoprodol to become a controlled substance at the federal level?	2008 Feb	18364610
Double-blind, placebo-controlled trial of carisoprodol 250-mg tablets in the treatment of acute lower-back spasm.	2008 Feb	18194591
Muscle and reflex changes with varying joint angle in hemiparetic stroke.	2008 Feb 27	18304313
Carisoprodol-induced amnestic state.	2008 Jan	19771317
[Toxicological screening of medicines and drugs of abuse in emergency cases].	2008 Jan 3	18183057
Carisoprodol withdrawal syndrome misdiagnosed as a psychotic disorder.	2008 Jul-Sep	18633744
Drug screening of hair by liquid chromatography-tandem mass spectrometry.	2008 Jun	18544222
Analysis of pain management drugs, specifically fentanyl, in hair: application to forensic specimens.	2008 Mar 21	18006260
Carisoprodol should be taken off the market.	2008 Oct	18791514
Novel transcriptional profile in wrist muscles from cerebral palsy patients.	2009 Jul 14	19602279
Quantitative analysis of carisoprodol and meprobamate in whole blood using benzylcarbamate and deuterated meprobamate as internal standards.	2009 Jun	19671248
Fibromyalgia and myofascial pain syndrome-a dilemma.	2009 Oct	20640108
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Regulation of intermittent oscillatory activity of pyramidal cell neurons by GABA inhibitory interneurons is impaired in schizophrenia: rationale for pharmacotherapeutic GABAergic interventions.	2010	20686196
Carisoprodol legal status and patterns of abuse.	2010 Dec	21062909
Pharmacogenetics and forensic toxicology.	2010 Dec 15	20828952
INCITE: A randomised trial comparing constraint induced movement therapy and bimanual training in children with congenital hemiplegia.	2010 Jan 12	20064275
Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry.	2010 Jan 22	20015510
Carisoprodol withdrawal after internet purchase.	2010 Jul	20592570
Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents.	2010 Jul 1	20521847
The relation between neuromechanical parameters and Ashworth score in stroke patients.	2010 Jul 27	20663189
Adaptive robot training for the treatment of incoordination in Multiple Sclerosis.	2010 Jul 29	20670420
Observations of medication compliance by measurement of urinary drug concentrations in a pain management population.	2010 Jul-Aug	20862905
Pharmacologic management of chronic pain.	2010 Jun	20556211
Quantification of the effects of an alpha-2 adrenergic agonist on reflex properties in spinal cord injury using a system identification technique.	2010 Jun 23	20573252
Comparison of drug concentrations in blood and oral fluid collected with the Intercept sampling device.	2010 May	20465866
Screening and quantitative determination of twelve acidic and neutral pharmaceuticals in whole blood by liquid-liquid extraction and liquid chromatography-tandem mass spectrometry.	2010 Sep	20822673

Patents

Sample Use Guides

In Vivo Use Guide

250 mg to 350 mg three times a day and at bedtime

Route of Administration: Oral

In Vitro Use Guide

HEK293 cells were transiently transfected with human alpha1beta2 and alpha1beta2gamma2 receptors. Whole-cell patch clamp electrophysiology was used to assess carisoprodol-activated Cl- current. EC50 value for carisoprodol was 142 ± 13 uM.

Name

Type

Language

CARISOPRODOL CIV

Preferred Name

English

CARISOPRODOL

Official Name

English

(±)-2-METHYL-2-PROPYL-1,3-PROPANEDIOL CARBAMATE ISOPROPYLCARBAMATE

Systematic Name

English

CARISOPRODOL [HSDB]

Common Name

English

CARISOPRODOL [USP MONOGRAPH]

Common Name

English

NSC-172124

Code

English

CARISOPRODOL [MI]

Common Name

English

CARISOPRODOL [EP IMPURITY]

Common Name

English

CARISOPRODOL [JAN]

Common Name

English

carisoprodol [INN]

Common Name

English

SOMA

Brand Name

English

Carisoprodol [WHO-DD]

Common Name

English

RELA

Brand Name

English

SOMA COMPOUND COMPONENT CARISOPRODOL

Common Name

English

CARISOPRODOL [VANDF]

Common Name

English

CARISOPRODOL [ORANGE BOOK]

Common Name

English

CARISOPRODOL CIV [USP-RS]

Common Name

English

CARISOPRODOL COMPOUND COMPONENT CARISOPRODOL

Common Name

English

CARISOPRODOL [MART.]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175737