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)
DescriptionCurator'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
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/13799302
Curator's Comment: Carisoprodol was developed in the 1950s by Dr. Frank M. Berger at Wallace laboratories on the basis of meprobamate.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364024 Sources: http://www.ncbi.nlm.nih.gov/pubmed/20419052 |
142.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | SOMA Approved UseSOMA 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 Date1959 |
Cmax
Value | Dose | Co-administered | 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 |
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 |
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 |
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 |
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 |
T1/2
Value | Dose | Co-administered | 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 |
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 |
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 |
Funbound
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.5%) Sources: 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%) |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.7%) Sources: 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%) |
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: |
unhealthy, adult |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal distension | 0.2% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Diarrhea | 0.2% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Intervertebral disc protrusion | 0.2% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Pain in extremity | 0.2% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Stomach discomfort | 0.2% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Upper abdominal pain | 0.2% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Dizziness | 0.5% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Headache | 0.5% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Disorientation | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Fatigue | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Headache | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Intervertebral disc protrusion | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Nausea | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Nephrolithiasis | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Paraesthesia | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Rash | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Skin papilloma | 0.4% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Dizziness | 0.7% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Somnolence | 0.7% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Stomach discomfort | 0.7% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Upper abdominal pain | 0.7% Disc. AE |
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: |
unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 333.0 |
weak | |||
Page: 333.0 |
weak | |||
Page: 333.0 |
weak |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
major | |||
Page: 1012.0 |
yes | |||
Page: 1012.0 |
yes | |||
Page: 1012.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
|
Abuse of combinations of carisoprodol and tramadol. | 2001 May |
|
[Guidelines concerning acute low back pain]. | 2002 Apr 30 |
|
Urticaria to carisoprodol. | 2002 Jan |
|
[Carisoprodol--one more time]. | 2002 Jan 30 |
|
Carisoprodol: an unrecognized drug of abuse. | 2002 Mar |
|
Somatic dysfunction during carisoprodol cessation: evidence for a carisoprodol withdrawal syndrome. | 2003 Feb |
|
Association between blood carisoprodol:meprobamate concentration ratios and CYP2C19 genotype in carisoprodol-drugged drivers: decreased metabolic capacity in heterozygous CYP2C19*1/CYP2C19*2 subjects? | 2003 Jul |
|
Possible dangerous interaction of oxycontin and carisoprodol. | 2003 Jun 1 |
|
Possible dangerous interaction of oxycontin and carisoprodol. | 2003 Mar 1 |
|
A near-fatal overdose of carisoprodol (SOMA): case report. | 2004 |
|
Tolerance and dependence risk with the use of carisoprodol. | 2004 Apr 1 |
|
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 |
|
Fatal intoxications in a Swedish forensic autopsy material during 1992-2002. | 2004 Jun 30 |
|
Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. | 2004 Sep |
|
The CYP2C19 genotype and the use of oral contraceptives influence the pharmacokinetics of carisoprodol in healthy human subjects. | 2005 Aug |
|
Human pharmaceuticals, hormones, and personal care product ingredients in runoff from agricultural fields irrigated with treated wastewater. | 2005 Mar 9 |
|
Treatment of carisoprodol dependence: a case report. | 2005 Sep |
|
Carisoprodol abuse in Texas, 1998-2003. | 2006 Mar |
|
Carisoprodol abuse in Mississippi. | 2007 Dec |
|
Is the frequency of carisoprodol withdrawal syndrome increasing? | 2007 Oct |
|
Acute intoxications with carisoprodol. | 2008 Apr |
|
Reliability of Ashworth and Modified Ashworth scales in children with spastic cerebral palsy. | 2008 Apr 10 |
|
Is it time for carisoprodol to become a controlled substance at the federal level? | 2008 Feb |
|
Double-blind, placebo-controlled trial of carisoprodol 250-mg tablets in the treatment of acute lower-back spasm. | 2008 Feb |
|
Muscle and reflex changes with varying joint angle in hemiparetic stroke. | 2008 Feb 27 |
|
Carisoprodol-induced amnestic state. | 2008 Jan |
|
[Toxicological screening of medicines and drugs of abuse in emergency cases]. | 2008 Jan 3 |
|
Carisoprodol withdrawal syndrome misdiagnosed as a psychotic disorder. | 2008 Jul-Sep |
|
Drug screening of hair by liquid chromatography-tandem mass spectrometry. | 2008 Jun |
|
Analysis of pain management drugs, specifically fentanyl, in hair: application to forensic specimens. | 2008 Mar 21 |
|
Carisoprodol should be taken off the market. | 2008 Oct |
|
Novel transcriptional profile in wrist muscles from cerebral palsy patients. | 2009 Jul 14 |
|
Quantitative analysis of carisoprodol and meprobamate in whole blood using benzylcarbamate and deuterated meprobamate as internal standards. | 2009 Jun |
|
Fibromyalgia and myofascial pain syndrome-a dilemma. | 2009 Oct |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Regulation of intermittent oscillatory activity of pyramidal cell neurons by GABA inhibitory interneurons is impaired in schizophrenia: rationale for pharmacotherapeutic GABAergic interventions. | 2010 |
|
Carisoprodol legal status and patterns of abuse. | 2010 Dec |
|
Pharmacogenetics and forensic toxicology. | 2010 Dec 15 |
|
INCITE: A randomised trial comparing constraint induced movement therapy and bimanual training in children with congenital hemiplegia. | 2010 Jan 12 |
|
Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry. | 2010 Jan 22 |
|
Carisoprodol withdrawal after internet purchase. | 2010 Jul |
|
Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents. | 2010 Jul 1 |
|
The relation between neuromechanical parameters and Ashworth score in stroke patients. | 2010 Jul 27 |
|
Adaptive robot training for the treatment of incoordination in Multiple Sclerosis. | 2010 Jul 29 |
|
Observations of medication compliance by measurement of urinary drug concentrations in a pain management population. | 2010 Jul-Aug |
|
Pharmacologic management of chronic pain. | 2010 Jun |
|
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 |
|
Comparison of drug concentrations in blood and oral fluid collected with the Intercept sampling device. | 2010 May |
|
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 |
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19244096
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.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175737
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LIVERTOX |
NBK548829
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WHO-ATC |
M03BA72
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WHO-VATC |
QM03BA72
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WHO-VATC |
QM03BA52
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WHO-ATC |
M03BA02
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NCI_THESAURUS |
C29696
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WHO-VATC |
QM03BA02
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DEA NO. |
8192
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WHO-ATC |
M03BA52
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NDF-RT |
N0000175730
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C28904
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D002328
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100000084595
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1096600
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CARISOPRODOL
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Carisoprodol
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CHEMBL1233
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ACTIVE MOIETY