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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H26N2O4
Molecular Weight 406.4751
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARVEDILOL, (+)-

SMILES

COc1ccccc1OCCNC[C@]([H])(COc2cccc3c2c4ccccc4[nH]3)O

InChI

InChIKey=OGHNVEJMJSYVRP-QGZVFWFLSA-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/t17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C24H26N2O4
Molecular Weight 406.4751
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

(R)-carvedilol, an enantiomer of the drug carvedilol, which is used in the treatment of mild to moderate congestive heart failure. (R)-carvedilol is an alpha adrenergic receptor blocker. It was shown, that (R)-carvedilol increased sympathetic tone, presumably as a physiological reaction to the decrease in blood pressure caused by alpha-blockade. The weak clinical net effect of beta-blockade of (R, S)-carvedilol at rest might be one reason why this drug causes fewer side effects than other beta-blockers, such as a reduction of nocturnal melatonin release.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Stereoselective effects of (R)- and (S)-carvedilol in humans.
2001 Jul

Sample Use Guides

It was performed a randomized, double-blind, placebo-controlled, crossover study in 12 healthy male volunteers. Subjects received single oral doses of 25 mg (R,S)-carvedilol, 12.5 mg (R)/(+)-carvedilol, 12.5 mg (S)/(-)-carvedilol, and placebo at 8 AM as well as at 8 PM. Compared to placebo, (R)-carvedilol increased heart rate during exercise (+4%, P < 0.05) and recovery (+10%, P < 0.05); (S)-carvedilol decreased heart rate during exercise (-14%, P < 0.05) and recovery (-6%, P < 0.05), and systolic blood pressure during exercise (-12%, P < 0.05); (R,S)-carvedilol decreased heart rate during exercise (-11%, P < 0.05), and systolic blood pressure at rest (-7%, P < 0.05) and during exercise (-10%, P < 0.05).
Route of Administration: Oral
The aim of this study was to clarify the mechanisms for the enhancing effect of amiodarone on R- and S-carvedilol glucuronidation. It was evaluated O-Glu formation of R- and S-carvedilol enantiomers in a reaction mixture of HLM including 0.2% bovine serum albumin (BSA). In the absence of amiodarone, glucuronidation activity of R- and S-carvedilol (final concentration of 0.2–400 μM) for 25 min was 0.026, and 0.51 pmol/min/mg protein, and that was increased by 6.15 and 1.60-fold in the presence of 50 µM amiodarone, respectively. Generally, the metabolism of S(−)- carvedilol in vitro was more rapid than that of the R(+) enantiomer.
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:44:54 UTC 2021
Edited
by admin
on Sat Jun 26 06:44:54 UTC 2021
Record UNII
N6E193E020
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARVEDILOL, (+)-
Common Name English
2-PROPANOL, 1-(9H-CARBAZOL-4-YLOXY)-3-((2-(2-METHOXYPHENOXY)ETHYL)AMINO)-, (2R)-
Systematic Name English
CARVEDILOL, R-(+)-
Common Name English
R-(+)-CARVEDILOL
Common Name English
(R)-CARVEDILOL
Common Name English
(+)-CARVEDILOL
Common Name English
Code System Code Type Description
FDA UNII
N6E193E020
Created by admin on Sat Jun 26 06:44:54 UTC 2021 , Edited by admin on Sat Jun 26 06:44:54 UTC 2021
PRIMARY
EPA CompTox
95093-99-5
Created by admin on Sat Jun 26 06:44:54 UTC 2021 , Edited by admin on Sat Jun 26 06:44:54 UTC 2021
PRIMARY
CAS
95093-99-5
Created by admin on Sat Jun 26 06:44:54 UTC 2021 , Edited by admin on Sat Jun 26 06:44:54 UTC 2021
PRIMARY
PUBCHEM
185394
Created by admin on Sat Jun 26 06:44:54 UTC 2021 , Edited by admin on Sat Jun 26 06:44:54 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
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METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT