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Details

Stereochemistry RACEMIC
Molecular Formula C24H26N2O4.H2O.H3O4P
Molecular Weight 522.4847
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARVEDILOL PHOSPHATE MONOHYDRATE

SMILES

O.OP(O)(O)=O.COC1=CC=CC=C1OCCNCC(O)COC2=CC=CC3=C2C4=C(N3)C=CC=C4

InChI

InChIKey=JAYBFQXVKDGMFT-UHFFFAOYSA-N
InChI=1S/C24H26N2O4.H3O4P.H2O/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;1-5(2,3)4;/h2-12,17,25-27H,13-16H2,1H3;(H3,1,2,3,4);1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H26N2O4
Molecular Weight 406.4742
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula H3O4P
Molecular Weight 97.9952
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Using isoproterenol stress echocardiography to predict the response to carvedilol in patients with dilated cardiomyopathy.
2001 Jun
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
Patents

Sample Use Guides

In Vivo Use Guide
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 after intervals 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
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 Tue Oct 22 19:38:34 UTC 2019
Edited
by admin
on Tue Oct 22 19:38:34 UTC 2019
Record UNII
4S19O2F64L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARVEDILOL PHOSPHATE MONOHYDRATE
Common Name English
2-PROPANOL, 1-(9H-CARBAZOL-4-YLOXY)-3-((2-(2-METHOXYPHENOXY)ETHYL)AMINO)-, PHOSPHATE, HYDRATE (1:1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
23649704
Created by admin on Tue Oct 22 19:38:34 UTC 2019 , Edited by admin on Tue Oct 22 19:38:34 UTC 2019
PRIMARY
CAS
1196658-85-1
Created by admin on Tue Oct 22 19:38:34 UTC 2019 , Edited by admin on Tue Oct 22 19:38:34 UTC 2019
PRIMARY
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