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Details

Stereochemistry RACEMIC
Molecular Formula C24H26N2O5
Molecular Weight 422.4736
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXYCARVEDILOL

SMILES

COC1=C(OCCNCC(O)COC2=CC=CC3=C2C4=C(N3)C=CC=C4)C=CC(O)=C1

InChI

InChIKey=ZCJHEORDHXCJNB-UHFFFAOYSA-N
InChI=1S/C24H26N2O5/c1-29-23-13-16(27)9-10-21(23)30-12-11-25-14-17(28)15-31-22-8-4-7-20-24(22)18-5-2-3-6-19(18)26-20/h2-10,13,17,25-28H,11-12,14-15H2,1H3

HIDE SMILES / InChI

Molecular Formula C24H26N2O5
Molecular Weight 422.4736
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

4'-Hydroxycarvedilol is a metabolite of Carvedilol. Incubation of R (+) - and S(-)-carvedilol with rat liver microsomes showed the formation of four oxidative metabolites: 1-hydroxycarvedilol (1-OHC), 8-hydroxycarvedilol (8-OHC), 4'-hydroxycarvedilol (4'-OHC), and O-desmethylcarvedilol (DesC). From in vivo metabolism studies were obtained, that 1-OHC and 8-OHC were the major products for both enantiomers used as a substrate. Also was invented, that 4'-hydroxycarvedilol slightly more effective than carvedilol in suppressing of store overload-induced calcium release (SOICR) through the cardiac ryanodine receptor (RyR2), which can trigger ventricular arrhythmias.

Approval Year

PubMed

PubMed

TitleDatePubMed
Oxidation of R(+)- and S(-)-carvedilol by rat liver microsomes. Evidence for stereoselective oxidation and characterization of the cytochrome P450 isozymes involved.
1994 Sep-Oct
Suppression of store overload-induced calcium release by hydroxylated metabolites of carvedilol.
2016 Jan 1
Substance Class Chemical
Created
by admin
on Tue Mar 06 11:28:54 UTC 2018
Edited
by admin
on Tue Mar 06 11:28:54 UTC 2018
Record UNII
I02L7A715Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-HYDROXYCARVEDILOL
Common Name English
4'-HYDROXYPHENYLCARVEDILOL
Common Name English
BM-140686
Code English
PHENOL, 4-(2-((3-(9H-CARBAZOL-4-YLOXY)-2-HYDROXYPROPYL)AMINO)ETHOXY)-3-METHOXY-
Systematic Name English
BM-14686
Code English
4'-HYDROXYCARVEDILOL
Common Name English
Code System Code Type Description
EPA CompTox
142227-49-4
Created by admin on Tue Mar 06 11:28:54 UTC 2018 , Edited by admin on Tue Mar 06 11:28:54 UTC 2018
PRIMARY
CAS
142227-49-4
Created by admin on Tue Mar 06 11:28:54 UTC 2018 , Edited by admin on Tue Mar 06 11:28:54 UTC 2018
PRIMARY
PUBCHEM
4572774
Created by admin on Tue Mar 06 11:28:54 UTC 2018 , Edited by admin on Tue Mar 06 11:28:54 UTC 2018
PRIMARY
Related Record Type Details
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