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)
Molecular Formula | C12H24N2O4 |
Molecular Weight | 260.33 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
---|---|---|
National All Schedules Prescription Electronic Reporting Act (NASPER): balancing substance abuse and medical necessity. | 2002 Jul |
|
A near-fatal overdose of carisoprodol (SOMA): case report. | 2004 |
|
Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. | 2004 Aug |
|
Prescription of nonsteroidal anti-inflammatory drugs and muscle relaxants for back pain in the United States. | 2004 Dec 1 |
|
Impairment due to intake of carisoprodol. | 2004 Jun 11 |
|
Identifying controlled substance patterns of utilization requiring evaluation using administrative claims data. | 2004 Nov |
|
Stimulant and relaxant drugs combined with stimulant and relaxant information: a study of active placebo. | 2004 Nov |
|
Recent trends of drug abuse and drug-associated deaths in Korea. | 2004 Oct |
|
Simultaneous determination of carisoprodol and meprobamate in human hair using solid-phase extraction and gas chromatography/mass spectrometry of the trimethylsilyl derivatives. | 2005 |
|
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 |
|
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs. | 2005 Sep-Oct |
|
Biology and therapy of fibromyalgia. New therapies in fibromyalgia. | 2006 |
|
A one-step and sensitive GC-MS assay for meprobamate determination in emergency situations. | 2006 Jun |
|
Carisoprodol withdrawal induced delirium: A case study. | 2007 |
|
Carisoprodol use and abuse in Norway: a pharmacoepidemiological study. | 2007 Aug |
|
Carisoprodol abuse in Mississippi. | 2007 Dec |
|
Drug screening of preserved oral fluid by liquid chromatography-tandem mass spectrometry. | 2007 Feb |
|
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 |
|
[Somadril will be recalled June 1, 2008]. | 2008 Apr 2-8 |
|
Carisoprodol withdrawal syndrome misdiagnosed as a psychotic disorder. | 2008 Jul-Sep |
|
Drug screening of hair by liquid chromatography-tandem mass spectrometry. | 2008 Jun |
|
[The Somadril Association in Norway]. | 2008 Jun 26 |
|
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 |
|
Effects of naltrexone on pain sensitivity and mood in fibromyalgia: no evidence for endogenous opioid pathophysiology. | 2009 |
|
Novel transcriptional profile in wrist muscles from cerebral palsy patients. | 2009 Jul 14 |
|
A multi-drug intoxication fatality involving Xyrem (GHB). | 2009 Mar |
|
[Prescription shopping of addictive drugs in Norway]. | 2009 Mar 12 |
|
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 |
|
Fibromyalgia and myofascial pain syndrome-a dilemma. | 2009 Oct |
|
Introduction of low dose transdermal buprenorphine -- did it influence use of potentially addictive drugs in chronic non-malignant pain patients? | 2009 Oct |
|
Regulation of intermittent oscillatory activity of pyramidal cell neurons by GABA inhibitory interneurons is impaired in schizophrenia: rationale for pharmacotherapeutic GABAergic interventions. | 2010 |
|
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 |
|
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 |
|
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 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:45:36 GMT 2025
by
admin
on
Mon Mar 31 17:45:36 GMT 2025
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Record UNII |
21925K482H
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Record Status |
Validated (UNII)
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Record Version |
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-
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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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3021
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DB00395
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DTXSID8024733
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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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SUB06631MIG
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201-118-7
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m3112
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PRIMARY | Merck Index | ||
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2101
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902
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CHEMBL1233
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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