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 179		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 8360	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 -3.38688016E11

C_max

Value	Dose	Analyte	Population
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
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

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
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
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

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 Page: 6	unhealthy, 41 years n = 548 Health Status: unhealthy Condition: acute, mechanical, lower back pain Age Group: 41 years Sex: M+F Population Size: 548 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf Page: 6	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 Page: 6
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 Page: 6	unhealthy, 41 years n = 279 Health Status: unhealthy Condition: acute, mechanical, lower back pain Age Group: 41 years Sex: M+F Population Size: 279 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/011792Orig1s041.pdf Page: 6	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 Page: 6
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 n = 9 Health Status: unhealthy Age Group: adult Sex: M Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/1998178	Sources: https://pubmed.ncbi.nlm.nih.gov/1998178

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1579 substrate 1709		inhibitor 1837 substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 901	CYP2C19 985 CYP1A2 1032

Drug as perpetrator

Target	Modality	Activity
CYP2C8 955	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak
CYP2D6 1875	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak
CYP3A4 1909	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak

Drug as victim

Target	Modality	Activity
CYP2C19 985	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/011792s050lbl.pdf Page: 4.0	major
CYP1A2 1032	substrate 3326 Sources: https://link.springer.com/article/10.1007/s40262-016-0373-8 Page: 1012.0	yes
CYP2D6 1193	substrate 3326 Sources: https://link.springer.com/article/10.1007/s40262-016-0373-8 Page: 1012.0	yes
CYP3A4 1709	substrate 3326 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
Carisoprodol abuse in Texas, 1998-2003.	2006 Mar	18072105
Carisoprodol withdrawal induced delirium: A case study.	2007	19300598
Carisoprodol abuse in Mississippi.	2007 Dec	19292137
Upper limb impairments associated with spasticity in neurological disorders.	2007 Nov 29	18047660
Abuse potential of carisoprodol: a retrospective review of Idaho Medicaid pharmacy and medical claims data.	2007 Oct	18042478
Inhalant abuse: A clinic-based study.	2008 Apr	19742220
[Somadril will be recalled June 1, 2008].	2008 Apr 2-8	18478757
Are there alternatives to the use of quinine to treat nocturnal leg cramps?	2008 Feb	18454580
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
[The Somadril Association in Norway].	2008 Jun 26	18587468
Analysis of pain management drugs, specifically fentanyl, in hair: application to forensic specimens.	2008 Mar 21	18006260
[Somadril is accessible after May 1, 2008].	2008 May 1	18451900
Urine drug testing of chronic pain patients: licit and illicit drug patterns.	2008 Oct	19007501
Carisoprodol-induced amnestic state and nocturnal blackouts.	2008 Oct	18792430
Carisoprodol should be taken off the market.	2008 Oct	18791514
Effects of naltrexone on pain sensitivity and mood in fibromyalgia: no evidence for endogenous opioid pathophysiology.	2009	19365548
Novel transcriptional profile in wrist muscles from cerebral palsy patients.	2009 Jul 14	19602279
Reliability and validity of pendulum test measures of spasticity obtained with the Polhemus tracking system from patients with chronic stroke.	2009 Jul 30	19642989
Quantitative analysis of carisoprodol and meprobamate in whole blood using benzylcarbamate and deuterated meprobamate as internal standards.	2009 Jun	19671248
A multi-drug intoxication fatality involving Xyrem (GHB).	2009 Mar	19187456
[Prescription shopping of addictive drugs in Norway].	2009 Mar 12	19282887
Prescription pattern of codeine for non-malignant pain: a pharmacoepidemiological study from the Norwegian Prescription Database.	2009 May	19419357
Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies.	2009 May	19244096
A pilot study evaluating use of a computer-assisted neurorehabilitation platform for upper-extremity stroke assessment.	2009 May 28	19476637
The effect of scheduling and withdrawal of carisoprodol on prevalence of intoxications with the drug.	2009 Nov	19663822
Fibromyalgia and myofascial pain syndrome-a dilemma.	2009 Oct	20640108
Introduction of low dose transdermal buprenorphine -- did it influence use of potentially addictive drugs in chronic non-malignant pain patients?	2009 Oct	19095476
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
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010 Apr 7	20396637
Carisoprodol legal status and patterns of abuse.	2010 Dec	21062909
Rapid and sensitive LC-MS/MS method for determination of felbamate in mouse plasma and tissues and human plasma.	2010 Dec 15	21081288
Pharmacogenetics and forensic toxicology.	2010 Dec 15	20828952
Clinical perspective: monitoring sodium oxybate-treated narcolepsy patients for the development of sleep-disordered breathing.	2010 Feb	19626356
Randomized, double-blind trial of carisoprodol 250 mg compared with placebo and carisoprodol 350 mg for the treatment of low back spasm.	2010 Jan	19908948
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
Carisoprodol: abuse potential and withdrawal syndrome.	2010 Mar	20088817
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

Official Name

English

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

Systematic Name

English

CARISOPRODOL [HSDB]

Common Name

English

CARISOPRODOL COMPONENT OF CARISOPRODOL COMPOUND

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

CARISOPRODOL CIV

Common Name

English

CARISOPRODOL COMPONENT OF SOMA COMPOUND

Common 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