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
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)
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 | ( + / - ) |
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 Date-3.38688016E11 |
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 |
|
[Carisoprodol--one more time]. | 2002 Jan 30 |
|
Simultaneous determination of carisoprodol and acetaminophen in an attempted suicide by liquid chromatography-mass spectrometry with positive electrospray ionization. | 2003 Mar |
|
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 |
|
Human pharmaceuticals, hormones, and personal care product ingredients in runoff from agricultural fields irrigated with treated wastewater. | 2005 Mar 9 |
|
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs. | 2005 Sep-Oct |
|
Carisoprodol withdrawal induced delirium: A case study. | 2007 |
|
Carisoprodol abuse in Mississippi. | 2007 Dec |
|
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 |
|
Reliability of Ashworth and Modified Ashworth scales in children with spastic cerebral palsy. | 2008 Apr 10 |
|
Double-blind, placebo-controlled trial of carisoprodol 250-mg tablets in the treatment of acute lower-back spasm. | 2008 Feb |
|
[Toxicological screening of medicines and drugs of abuse in emergency cases]. | 2008 Jan 3 |
|
[The Somadril Association in Norway]. | 2008 Jun 26 |
|
Effects of naltrexone on pain sensitivity and mood in fibromyalgia: no evidence for endogenous opioid pathophysiology. | 2009 |
|
Reliability and validity of pendulum test measures of spasticity obtained with the Polhemus tracking system from patients with chronic stroke. | 2009 Jul 30 |
|
[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 |
|
Fibromyalgia and myofascial pain syndrome-a dilemma. | 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 |
|
Carisoprodol legal status and patterns of abuse. | 2010 Dec |
|
Rapid and sensitive LC-MS/MS method for determination of felbamate in mouse plasma and tissues and human plasma. | 2010 Dec 15 |
|
INCITE: A randomised trial comparing constraint induced movement therapy and bimanual training in children with congenital hemiplegia. | 2010 Jan 12 |
|
Carisoprodol: abuse potential and withdrawal syndrome. | 2010 Mar |
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
Fri Jun 25 20:56:20 UTC 2021
by
admin
on
Fri Jun 25 20:56:20 UTC 2021
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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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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175737
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LIVERTOX |
151
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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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Code System | Code | Type | Description | ||
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C28904
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PRIMARY | |||
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D002328
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PRIMARY | |||
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CARISOPRODOL
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1096600
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Carisoprodol
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PRIMARY | |||
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21925K482H
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7610
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3021
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DB00395
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78-44-4
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2576
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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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PRIMARY | |||
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M3112
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PRIMARY | Merck Index | ||
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2101
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PRIMARY | RxNorm | ||
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902
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CHEMBL1233
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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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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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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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