Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H26N2O4 |
Molecular Weight | 406.4742 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OCCNCC(O)COC2=CC=CC3=C2C4=C(N3)C=CC=C4)C=CC=C1
InChI
InChIKey=OGHNVEJMJSYVRP-UHFFFAOYSA-N
InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3
Molecular Formula | C24H26N2O4 |
Molecular Weight | 406.4742 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Carvedilol competitively blocks β1, β2 and α1 receptors. The drug lacks sympathomimetic activity and has vasodilating properties that are exerted primarily through α1-blockade. Animal models indicate that carvedilol confers protection against myocardial necrosis, arrhythmia and cell damage caused by oxidising free radicals, and the drug has no adverse effects on plasma lipid profiles. COREG® (carvedilol) is a racemic mixture in which nonselective β-adrenoreceptor blocking activity is present in the S(-) enantiomer and α1-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol is the first drug of its kind to be approved for the treatment of congestive heart failure, and is now the standard of care for this devastating disease. Carvedilol is also confirmed as effective in the management of mild to moderate hypertension and ischaemic heart disease.
Originator
Sources: http://www.google.com/patents/US4503067
Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/carvedilol.html
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094118 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | COREG Approved UseCOREG® (carvedilol) is indicated for the treatment of mild-to-severe chronic heart failure of ischemic or cardiomyopathic origin, usually in addition to diuretics, ACE inhibitors, and digitalis, to increase survival and, also, to reduce the risk of hospitalization.
COREG is indicated to reduce cardiovascular mortality in clinically stable patients who
have survived the acute phase of a myocardial infarction and have a left ventricular ejection fraction of ≤40% (with or without symptomatic heart failure).
COREG is indicated for the management of essential hypertension. It can be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. Launch Date8.1103677E11 |
|||
Primary | COREG Approved UseCOREG® (carvedilol) is indicated for the treatment of mild-to-severe chronic heart failure of ischemic or cardiomyopathic origin, usually in addition to diuretics, ACE inhibitors, and digitalis, to increase survival and, also, to reduce the risk of hospitalization.
COREG is indicated to reduce cardiovascular mortality in clinically stable patients who
have survived the acute phase of a myocardial infarction and have a left ventricular ejection fraction of ≤40% (with or without symptomatic heart failure).
COREG is indicated for the management of essential hypertension. It can be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. Launch Date8.1103677E11 |
|||
Primary | COREG Approved UseCOREG® (carvedilol) is indicated for the treatment of mild-to-severe chronic heart failure of ischemic or cardiomyopathic origin, usually in addition to diuretics, ACE inhibitors, and digitalis, to increase survival and, also, to reduce the risk of hospitalization.
COREG is indicated to reduce cardiovascular mortality in clinically stable patients who
have survived the acute phase of a myocardial infarction and have a left ventricular ejection fraction of ≤40% (with or without symptomatic heart failure).
COREG is indicated for the management of essential hypertension. It can be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. Launch Date8.1103677E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10934668 |
6.25 mg 2 times / day steady-state, oral dose: 6.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CARVEDILOL, (+)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
8.46 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10934668 |
6.25 mg 2 times / day steady-state, oral dose: 6.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CARVEDILOL, (-)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
26.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10934668 |
6.25 mg 2 times / day steady-state, oral dose: 6.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CARVEDILOL plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
94.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10934668 |
6.25 mg 2 times / day steady-state, oral dose: 6.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CARVEDILOL, (+)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
42.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10934668 |
6.25 mg 2 times / day steady-state, oral dose: 6.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CARVEDILOL, (-)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
139 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10934668 |
6.25 mg 2 times / day steady-state, oral dose: 6.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CARVEDILOL plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Co-administed with:: lorazepam(7 mg) Sources: |
unknown, 41 years n = 1 Health Status: unknown Age Group: 41 years Sex: M Population Size: 1 Sources: |
Other AEs: Wheezing... |
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy, 66.7±12.0 years n = 7 Health Status: unhealthy Condition: chronic heart failure Age Group: 66.7±12.0 years Sex: M+F Population Size: 7 Sources: |
|
375 mg single, oral Overdose Dose: 375 mg Route: oral Route: single Dose: 375 mg Co-administed with:: simvastatin(fifteen 20-mg tablets) Sources: |
unhealthy, 84 years n = 1 Health Status: unhealthy Age Group: 84 years Sex: M Population Size: 1 Sources: |
Other AEs: Hypotension... |
50 mg 1 times / day steady, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 765 Health Status: unhealthy Condition: heart failure Age Group: adult Population Size: 765 Sources: |
Disc. AE: Hypotension... AEs leading to discontinuation/dose reduction: Hypotension (0.7%) Sources: |
20 mg 2 times / day multiple, oral Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: Page: p. 61 |
unhealthy, adult n = 54 Health Status: unhealthy Age Group: adult Population Size: 54 Sources: Page: p. 61 |
Disc. AE: Congestive cardiac failure... AEs leading to discontinuation/dose reduction: Congestive cardiac failure (moderate, 1 patient) Sources: Page: p. 61 |
25 mg 2 times / day steady, oral Dose: 25 mg, 2 times / day Route: oral Route: steady Dose: 25 mg, 2 times / day Sources: |
unhealthy, adult n = 1156 Health Status: unhealthy Condition: severe heart failure Age Group: adult Population Size: 1156 Sources: |
Disc. AE: Dizziness... AEs leading to discontinuation/dose reduction: Dizziness (1.3%) Sources: |
6.25 mg 2 times / day multiple, oral Dose: 6.25 mg, 2 times / day Route: oral Route: multiple Dose: 6.25 mg, 2 times / day Sources: Page: p. 61 |
unhealthy, adult n = 54 Health Status: unhealthy Age Group: adult Population Size: 54 Sources: Page: p. 61 |
Disc. AE: Abdominal distension... AEs leading to discontinuation/dose reduction: Abdominal distension (1 patient) Sources: Page: p. 61 |
6.25 mg 2 times / day multiple, oral Dose: 6.25 mg, 2 times / day Route: oral Route: multiple Dose: 6.25 mg, 2 times / day Sources: Page: p. 61 |
unhealthy, adult n = 54 Health Status: unhealthy Age Group: adult Population Size: 54 Sources: Page: p. 61 |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (moderate, 1 patient) Sources: Page: p. 61 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Wheezing | 1 patient | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Co-administed with:: lorazepam(7 mg) Sources: |
unknown, 41 years n = 1 Health Status: unknown Age Group: 41 years Sex: M Population Size: 1 Sources: |
Hypotension | 1 patient | 375 mg single, oral Overdose Dose: 375 mg Route: oral Route: single Dose: 375 mg Co-administed with:: simvastatin(fifteen 20-mg tablets) Sources: |
unhealthy, 84 years n = 1 Health Status: unhealthy Age Group: 84 years Sex: M Population Size: 1 Sources: |
Hypotension | 0.7% Disc. AE |
50 mg 1 times / day steady, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 765 Health Status: unhealthy Condition: heart failure Age Group: adult Population Size: 765 Sources: |
Congestive cardiac failure | moderate, 1 patient Disc. AE |
20 mg 2 times / day multiple, oral Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: Page: p. 61 |
unhealthy, adult n = 54 Health Status: unhealthy Age Group: adult Population Size: 54 Sources: Page: p. 61 |
Dizziness | 1.3% Disc. AE |
25 mg 2 times / day steady, oral Dose: 25 mg, 2 times / day Route: oral Route: steady Dose: 25 mg, 2 times / day Sources: |
unhealthy, adult n = 1156 Health Status: unhealthy Condition: severe heart failure Age Group: adult Population Size: 1156 Sources: |
Abdominal distension | 1 patient Disc. AE |
6.25 mg 2 times / day multiple, oral Dose: 6.25 mg, 2 times / day Route: oral Route: multiple Dose: 6.25 mg, 2 times / day Sources: Page: p. 61 |
unhealthy, adult n = 54 Health Status: unhealthy Age Group: adult Population Size: 54 Sources: Page: p. 61 |
Rash | moderate, 1 patient Disc. AE |
6.25 mg 2 times / day multiple, oral Dose: 6.25 mg, 2 times / day Route: oral Route: multiple Dose: 6.25 mg, 2 times / day Sources: Page: p. 61 |
unhealthy, adult n = 54 Health Status: unhealthy Age Group: adult Population Size: 54 Sources: Page: p. 61 |
PubMed
Title | Date | PubMed |
---|---|---|
Increase in doxorubicin cytotoxicity by carvedilol inhibition of P-glycoprotein activity. | 1999 Dec 1 |
|
Carvedilol enhances atrial and brain natriuretic peptide mRNA expression and release in rat heart. | 2000 |
|
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites. | 2000 Apr |
|
Carvedilol affects the physiological and behavioral response to smoked cocaine in humans. | 2000 Jul 1 |
|
Beta-blockers of the third generation inhibit endothelin-1 liberation, mRNA production and proliferation of human coronary smooth muscle and endothelial cells. | 2000 Nov |
|
Comitogenic effect of catecholamines on rat cardiac fibroblasts in culture. | 2000 Nov |
|
Levosimendan. | 2001 |
|
CAPRICORN: a story of alpha allocation and beta-blockers in left ventricular dysfunction post-MI. | 2001 Apr |
|
Carvedilol as therapy in pediatric heart failure: an initial multicenter experience. | 2001 Apr |
|
Carvedilol--a new dimension in pediatric heart failure therapy. | 2001 Apr |
|
50th Annual scientific sessions of the American college of cardiology. | 2001 Apr 10 |
|
Development of a capillary electrophoresis assay for the determination of carvedilol enantiomers in serum using cyclodextrins. | 2001 Feb |
|
Variceal bleeding and portal hypertension: still a therapeutic challenge? | 2001 Feb |
|
Differential effects of carvedilol and metoprolol on isoprenaline-induced changes in beta-adrenoceptor density and systolic function in rat cardiac myocytes. | 2001 Feb 1 |
|
Antiarrhythmic drug carvedilol inhibits HERG potassium channels. | 2001 Feb 1 |
|
Inhibitory effect of carvedilol in the high-conductance state of the mitochondrial permeability transition pore. | 2001 Feb 2 |
|
Beneficial effects of pentoxifylline in patients with idiopathic dilated cardiomyopathy treated with angiotensin-converting enzyme inhibitors and carvedilol: results of a randomized study. | 2001 Feb 27 |
|
Impressive amelioration of clinical (NYHA class) and echocardiographic parameters in heart failure patients treated with amiodarone and carvedilol. | 2001 Jan |
|
A placebo controlled evaluation of the antifibrillatory effects of carvedilol. | 2001 Jan |
|
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice. | 2001 Jan |
|
Inhibition of heart mitochondrial lipid peroxidation by non-toxic concentrations of carvedilol and its analog BM-910228. | 2001 Jan 15 |
|
Effect of carvedilol on atrioventricular conduction in the ischemic heart. | 2001 Jan 26 |
|
[Effects of carvedilol in rats with induced chronic kidney failure]. | 2001 Jan-Feb |
|
Effects of carvedilol on left ventricular function, mass, and scintigraphic findings in isolated left ventricular non-compaction. | 2001 Jul |
|
Catecholamines stimulate interleukin-6 synthesis in rat cardiac fibroblasts. | 2001 Jul |
|
Stereoselective effects of (R)- and (S)-carvedilol in humans. | 2001 Jul |
|
Using isoproterenol stress echocardiography to predict the response to carvedilol in patients with dilated cardiomyopathy. | 2001 Jun |
|
Beta-blockers to reduce mortality in patients with systolic dysfunction: a meta-analysis. | 2001 Jun |
|
Clinical Trials Update: CAPRICORN, COPERNICUS, MIRACLE, STAF, RITZ-2, RECOVER and RENAISSANCE and cachexia and cholesterol in heart failure. Highlights of the Scientific Sessions of the American College of Cardiology, 2001. | 2001 Jun |
|
Differing beta-blocking effects of carvedilol and metoprolol. | 2001 Jun |
|
Plasma brain natriuretic peptide as a novel therapeutic indicator in idiopathic dilated cardiomyopathy during beta-blocker therapy: a potential of hormone-guided treatment. | 2001 Jun |
|
Protective effect of carvedilol on chenodeoxycholate induction of the permeability transition pore. | 2001 Jun 1 |
|
Beta-blocker trials seem to be in conflict. | 2001 Jun 12 |
|
Beta-blockade in chronic heart failure. | 2001 Jun 12 |
|
Relationship between tumor necrosis factor-alpha production and oxidative stress in the failing hearts of patients with dilated cardiomyopathy. | 2001 Jun 15 |
|
Nebivolol, carvedilol and metoprolol do not influence cardiac Ca(2+) sensitivity. | 2001 Jun 22 |
|
Random research. | 2001 Jun 26 |
|
[Options in drug combinations]. | 2001 Mar |
|
[Adrenergic beta inhibitors in heart insufficiency: which and when?]. | 2001 Mar |
|
Determination of carvedilol in human cardiac tissue by high-performance liquid chromatography. | 2001 Mar |
|
[Severe heart failure. Carvedilol lowers mortality]. | 2001 Mar 1 |
|
What is the optimal medical management of ischemic heart failure? | 2001 Mar-Apr |
|
Does intention-to-treat analysis answer all questions in long-term mortality trials? Considerations on the basis of the ANZ trial. | 2001 May |
|
Influence of carvedilol on hospitalizations in heart failure: incidence, resource utilization and costs. U.S. Carvedilol Heart Failure Study Group. | 2001 May |
|
Carvedilol in the treatment of chronic heart failure. | 2001 May |
|
Carvedilol versus other beta-blockers in heart failure. | 2001 May |
|
Myocardial free fatty acid and glucose use after carvedilol treatment in patients with congestive heart failure. | 2001 May 22 |
|
Effect of carvedilol on survival in severe chronic heart failure. | 2001 May 31 |
|
Separation of carvedilol enantiomers in very small volumes of human plasma by capillary electrophoresis with laser-induced fluorescence. | 2001 May 5 |
|
Economic impact of beta blockade in heart failure. | 2001 May 7 |
Sample Use Guides
Take with food. Individualize dosage and monitor during up-titration.• Heart failure: Start at 3.125 mg twice daily and increase to 6.25, 12.5, and then 25 mg twice daily over intervals of at least 2 weeks. Maintain lower doses if higher doses are not tolerated.• Left ventricular dysfunction following myocardial infarction: Start at 6.25 mg twice daily and increase to 12.5 mg then 25 mg twice daily afterintervals of 3 to 10 days. A lower starting dose or slower titration may be used.• Hypertension: Start at 6.25 mg twice daily and increase if needed for blood pressure control to 12.5 mg then 25 mg twice daily over intervals of 1 to 2 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11991508
Compared with the PDGF-stimulated control, DNA synthesis decreased significantly to 60.3% +/- 10.4% and 18.3% +/- 5.9% in the presence of 1 and 10 microM of carvedilol, respectively (P < 0.05, each). Carvedilol significantly inhibited the activity of VSMCs stimulated by ET-1 and ANG-II. The IC50 of carvedilol was 1-10 microM. CsA only inhibited VSMCs significantly in the PDGF-stimulated subgroup. The addition of CsA in the presence of carvedilol did not affect the inhibitory activity of carvedilol. The pattern of inhibition in the combined group was uniform and similar to that of the carvedilol alone group, regardless of the stimulator used.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:29:36 UTC 2023
by
admin
on
Wed Jul 05 22:29:36 UTC 2023
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Record UNII |
0K47UL67F2
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000009923
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N0000175556
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WHO-ATC |
C07FX06
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LIVERTOX |
NBK548399
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N0000175553
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QC07AG02
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N0000009924
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NCI_THESAURUS |
C29576
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C07AG02
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NDF-RT |
N0000000099
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CHEMBL723
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DTXSID8022747
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0K47UL67F2
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1096622
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C043211
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C28906
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DB01136
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Carvedilol
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522
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ARTIST
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PRIMARY | APPROVED AUGUST 2015 | ||
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20352
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SUB06153MIG
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M3143
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100000092577
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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TARGET -> INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
Related Record | Type | Details | ||
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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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IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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HEART FAILURE, MORE THAN 85 kg |
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Volume of Distribution | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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