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 |
---|---|---|
Carvedilol enhances atrial and brain natriuretic peptide mRNA expression and release in rat heart. | 2000 |
|
Levosimendan. | 2001 |
|
[Clinical efficacy of carvedilol in patients with severe cardiac insufficiency]. | 2001 |
|
[Comparison of carvedilol and atenolol efficacy in patients with stable effort angina]. | 2001 |
|
Characterization of beta(1)-selectivity, adrenoceptor-G(s)-protein interaction and inverse agonism of nebivolol in human myocardium. | 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 |
|
Reducing readmissions for congestive heart failure. | 2001 Apr 15 |
|
Development of a capillary electrophoresis assay for the determination of carvedilol enantiomers in serum using cyclodextrins. | 2001 Feb |
|
[Economic study of carvedilol in heart failure. A cost effectiveness study in France]. | 2001 Feb |
|
Dilated cardiomyopathy in dialysis patients--beneficial effects of carvedilol: a double-blind, placebo-controlled trial. | 2001 Feb |
|
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 |
|
Detection of low levels of the amorphous phase in crystalline pharmaceutical materials by thermally stimulated current spectrometry. | 2001 Jan |
|
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 |
|
Effect of fluoxetine on carvedilol pharmacokinetics, CYP2D6 activity, and autonomic balance in heart failure patients. | 2001 Jan |
|
Sexual activity in hypertensive men treated with valsartan or carvedilol: a crossover study. | 2001 Jan |
|
Recovery of the cardiac adrenergic nervous system after long-term beta-blocker therapy in idiopathic dilated cardiomyopathy: assessment by increase in myocardial 123I-metaiodobenzylguanidine uptake. | 2001 Jan |
|
Current role of beta-adrenergic blockers in the treatment of chronic congestive heart failure. | 2001 Jan 15 |
|
[Comprehensive anti-adrenergic therapy. It can save the weak heart]. | 2001 Jan 25 |
|
Iodine-123 MIBG imaging before treatment of heart failure with carvedilol to predict improvement of left ventricular function and exercise capacity. | 2001 Jan-Feb |
|
Radical-scavenging and iron-chelating properties of carvedilol, an antihypertensive drug with antioxidative activity. | 2001 Jul 15 |
|
Using isoproterenol stress echocardiography to predict the response to carvedilol in patients with dilated cardiomyopathy. | 2001 Jun |
|
A cost-effectiveness analysis of bisoprolol for heart failure. | 2001 Jun |
|
Differing beta-blocking effects of carvedilol and metoprolol. | 2001 Jun |
|
Carvedilol increases plasma vascular endothelial growth factor (VEGF) in patients with chronic heart failure. | 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 |
|
Comparative effects of carvedilol and metoprolol on left ventricular ejection fraction in heart failure: results of a meta-analysis. | 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 |
|
Predicting response to carvedilol for the treatment of heart failure: a multivariate retrospective analysis. | 2001 Mar |
|
Extracellular matrix proteins in cardiac fibroblasts derived from rat hearts with chronic pressure overload: effects of beta-receptor blockade. | 2001 Mar |
|
Are all beta-blockers the same for chronic heart failure? | 2001 Mar |
|
[Severe heart failure. Carvedilol lowers mortality]. | 2001 Mar 1 |
|
What is the optimal medical management of ischemic heart failure? | 2001 Mar-Apr |
|
Benefits of beta-blockers in heart failure: a class specific effect? | 2001 May |
|
Mechanisms of carvedilol action in human congestive 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 |
|
Race and the response to adrenergic blockade with carvedilol in patients with chronic heart failure. | 2001 May 3 |
|
Effect of carvedilol on outcome after myocardial infarction in patients with left-ventricular dysfunction: the CAPRICORN randomised trial. | 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
Fri Dec 16 15:45:47 UTC 2022
by
admin
on
Fri Dec 16 15:45:47 UTC 2022
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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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Classification Tree | Code System | Code | ||
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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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WHO-VATC |
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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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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551
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M3143
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0K47UL67F2
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7044
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Carvedilol
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3441
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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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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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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TRANSPORTER -> INHIBITOR |
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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 | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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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 | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||
MAXIMUM TOLERATED DOSE | TOXICITY |
|
HEART FAILURE, MORE THAN 85 kg |
|
||
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
ORAL BIOAVAILABILITY | PHARMACOKINETIC |
|
|
|||