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

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

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	Positive Allosteric Modulator 179		142.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Painful musculoskeletal conditions 3	Palliative		Approved 8,429	SOMA

C_max

Value	Dose	Analyte	Population
1.2 μg/mL	250 mg single, oral	CARISOPRODOL plasma	Homo sapiens
1.8 μg/mL	350 mg single, oral	CARISOPRODOL plasma	Homo sapiens
13.3 μM	700 mg single, oral	CARISOPRODOL serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
4.5 μg × h/mL	250 mg single, oral		CARISOPRODOL plasma	Homo sapiens
7 μg × h/mL	350 mg single, oral		CARISOPRODOL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.7 h	250 mg single, oral	CARISOPRODOL plasma	Homo sapiens
2 h	350 mg single, oral	CARISOPRODOL plasma	Homo sapiens
99 min	700 mg single, oral	CARISOPRODOL serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
46%	700 mg single, oral		CARISOPRODOL serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
250 mg 3 times / day steady, oral Recommended	unhealthy, 41 years n = 548	Disc. AE: Dizziness, Headache...
350 mg 3 times / day steady, oral Recommended	unhealthy, 41 years n = 279	Disc. AE: Dizziness, Headache...
2100 mg 1 times / day steady, oral Highest studied dose	unhealthy, adult n = 9

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AEs

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AE	Significance	Dose	Population
Abdominal distension	0.2% Disc. AE	250 mg 3 times / day steady, oral Recommended	unhealthy, 41 years n = 548
Diarrhea	0.2% Disc. AE	250 mg 3 times / day steady, oral Recommended	unhealthy, 41 years n = 548
Intervertebral disc protrusion	0.2% Disc. AE	250 mg 3 times / day steady, oral Recommended	unhealthy, 41 years n = 548
Pain in extremity	0.2% Disc. AE	250 mg 3 times / day steady, oral Recommended	unhealthy, 41 years n = 548
Stomach discomfort	0.2% Disc. AE	250 mg 3 times / day steady, oral Recommended	unhealthy, 41 years n = 548

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 substrate 1,737		inhibitor 1,852 substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911	CYP2C19 991 CYP1A2 1,054

Drug as perpetrator

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Target	Modality	Activity
CYP2C8 965	inhibitor 3,277	weak
CYP2D6 1,891	inhibitor 3,277	weak
CYP3A4 1,925	inhibitor 3,277	weak

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Drug as victim

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Target	Modality	Activity
CYP2C19 991	substrate 3,367	major
CYP1A2 1,054	substrate 3,367	yes
CYP2D6 1,217	substrate 3,367	yes
CYP3A4 1,737	substrate 3,367	yes

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
[Guidelines concerning acute low back pain].	2002 Apr 30	12043062
Urticaria to carisoprodol.	2002 Jan	11991293
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

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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.

Show entries

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

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175737

Muscle relaxant

LIVERTOX

NBK548829

Carbamic acid esters

WHO-ATC

M03BA72

Carbamic acid esters

WHO-VATC

QM03BA72

Carbamic acid esters

WHO-VATC

QM03BA52

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Code System

Code

Type

Description

NCI_THESAURUS

C28904

PRIMARY

MESH

D002328

PRIMARY

SMS_ID

100000084595

PRIMARY

RS_ITEM_NUM

1096600

PRIMARY

WIKIPEDIA

CARISOPRODOL

PRIMARY

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ACTIVE MOIETY


					21925K482H

CARISOPRODOL

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator