CARISOPRODOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H24N2O4
Molecular Weight	260.3304
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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

Molecular Formula	C12H24N2O4
Molecular Weight	260.3304
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 157		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 8043	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 1467 substrate 1601		inhibitor 1702 substrate 1118

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 818	CYP2C19 910 CYP1A2 972

Drug as perpetrator

Target	Modality	Activity
CYP2C8 865	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak
CYP2D6 1738	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak
CYP3A4 1772	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12999 Page: 333.0	weak

Drug as victim

Target	Modality	Activity
CYP2C19 910	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/011792s050lbl.pdf Page: 4.0	major
CYP1A2 972	substrate 3113 Sources: https://link.springer.com/article/10.1007/s40262-016-0373-8 Page: 1012.0	yes
CYP2D6 1118	substrate 3113 Sources: https://link.springer.com/article/10.1007/s40262-016-0373-8 Page: 1012.0	yes
CYP3A4 1601	substrate 3113 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
[Carisoprodol--one more time].	2002 Jan 30	11894608
Simultaneous determination of carisoprodol and acetaminophen in an attempted suicide by liquid chromatography-mass spectrometry with positive electrospray ionization.	2003 Mar	12670008
Prescription of nonsteroidal anti-inflammatory drugs and muscle relaxants for back pain in the United States.	2004 Dec 1	15564901
Impairment due to intake of carisoprodol.	2004 Jun 11	15194209
Human pharmaceuticals, hormones, and personal care product ingredients in runoff from agricultural fields irrigated with treated wastewater.	2005 Mar 9	15740050
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs.	2005 Sep-Oct	16125625
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
Carisoprodol intoxications: a retrospective study of forensic autopsy material from 1992-2003.	2007 Sep	17115170
Reliability of Ashworth and Modified Ashworth scales in children with spastic cerebral palsy.	2008 Apr 10	18402701
Double-blind, placebo-controlled trial of carisoprodol 250-mg tablets in the treatment of acute lower-back spasm.	2008 Feb	18194591
[Toxicological screening of medicines and drugs of abuse in emergency cases].	2008 Jan 3	18183057
[The Somadril Association in Norway].	2008 Jun 26	18587468
Effects of naltrexone on pain sensitivity and mood in fibromyalgia: no evidence for endogenous opioid pathophysiology.	2009	19365548
Reliability and validity of pendulum test measures of spasticity obtained with the Polhemus tracking system from patients with chronic stroke.	2009 Jul 30	19642989
[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
Fibromyalgia and myofascial pain syndrome-a dilemma.	2009 Oct	20640108
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
Rapid and sensitive LC-MS/MS method for determination of felbamate in mouse plasma and tissues and human plasma.	2010 Dec 15	21081288
INCITE: A randomised trial comparing constraint induced movement therapy and bimanual training in children with congenital hemiplegia.	2010 Jan 12	20064275
Carisoprodol: abuse potential and withdrawal syndrome.	2010 Mar	20088817

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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:56:20 UTC 2021` Edited by `admin` on `Fri Jun 25 20:56:20 UTC 2021`
Record UNII	21925K482H
Record Status	`Validated (UNII)`
Record Version

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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

CARISOPRODOL [EP]

Common Name

English

NSC-172124

Code

English

CARISOPRODOL [MI]

Common Name

English

CARISOPRODOL [JAN]

Common Name

English

CARISOPRODOL [INN]

Common Name

English

SOMA

Brand 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 [WHO-DD]

Common Name

English

CARISOPRODOL COMPOUND COMPONENT CARISOPRODOL

Common Name

English

CARISOPRODOL [MART.]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175737