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 |
---|---|---|---|---|
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 |
|
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 |
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 |
---|---|---|---|---|
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 |
|
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 |
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: 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: Page: 6 |
Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.5%) Sources: Page: 6Headache (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: 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: Page: 6 |
Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.7%) Sources: Page: 6Headache (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 n = 9 Health Status: unhealthy Age Group: adult Sex: M Population Size: 9 Sources: |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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: 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: Page: 6 |
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 |
|
Blockade of reticular formation activity, due to carisoprodol maternal administration, and its effects on rat skeleton development. | 2002 |
|
[Carisoprodol--one more time]. | 2002 Jan 30 |
|
National All Schedules Prescription Electronic Reporting Act (NASPER): balancing substance abuse and medical necessity. | 2002 Jul |
|
Carisoprodol: an unrecognized drug of abuse. | 2002 Mar |
|
Somatic dysfunction during carisoprodol cessation: evidence for a carisoprodol withdrawal syndrome. | 2003 Feb |
|
Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. | 2004 Aug |
|
Carisoprodol withdrawal syndrome. | 2004 Dec |
|
Prescription of nonsteroidal anti-inflammatory drugs and muscle relaxants for back pain in the United States. | 2004 Dec 1 |
|
Treatment of carisoprodol dependence: a case report. | 2005 Sep |
|
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs. | 2005 Sep-Oct |
|
Do motor control genes contribute to interindividual variability in decreased movement in patients with pain? | 2007 Jul 26 |
|
[Somadril recalled in Norway]. | 2007 May 17 |
|
Upper limb impairments associated with spasticity in neurological disorders. | 2007 Nov 29 |
|
Carisoprodol intoxications: a retrospective study of forensic autopsy material from 1992-2003. | 2007 Sep |
|
Is it time for carisoprodol to become a controlled substance at the federal level? | 2008 Feb |
|
Carisoprodol-induced amnestic state. | 2008 Jan |
|
Carisoprodol withdrawal syndrome misdiagnosed as a psychotic disorder. | 2008 Jul-Sep |
|
High-dose carisoprodol during pregnancy and lactation. | 2008 Jun |
|
[The Somadril Association in Norway]. | 2008 Jun 26 |
|
[Somadril is accessible after May 1, 2008]. | 2008 May 1 |
|
Urine drug testing of chronic pain patients: licit and illicit drug patterns. | 2008 Oct |
|
Carisoprodol-induced amnestic state and nocturnal blackouts. | 2008 Oct |
|
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 |
|
Prescription pattern of codeine for non-malignant pain: a pharmacoepidemiological study from the Norwegian Prescription Database. | 2009 May |
|
Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. | 2009 May |
|
A pilot study evaluating use of a computer-assisted neurorehabilitation platform for upper-extremity stroke assessment. | 2009 May 28 |
|
Introduction of low dose transdermal buprenorphine -- did it influence use of potentially addictive drugs in chronic non-malignant pain patients? | 2009 Oct |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
|
Pharmacogenetics and forensic toxicology. | 2010 Dec 15 |
|
Clinical perspective: monitoring sodium oxybate-treated narcolepsy patients for the development of sleep-disordered breathing. | 2010 Feb |
|
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 |
|
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 |
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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21925K482H
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21925K482H
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3419
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7610
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DB00395
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2576
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172124
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78-44-4
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509
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m3112
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2101
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902
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CHEMBL1233
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ACTIVE MOIETY