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Details

Stereochemistry RACEMIC
Molecular Formula C24H26N2O5
Molecular Weight 422.4746
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXYCARVEDILOL

SMILES

COc1cc(ccc1OCCNCC(COc2cccc3c2c4ccccc4[nH]3)O)O

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 422.4746
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26584883

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment:: Three carvedilol metabolites hydroxylated at the 3-, 4' and 5'-positions were synthesized and assayed for store overload-induced calcium release (SOICR) inhibition in mutant HEK 293 cells expressing the RyR2 mutant R4496C. This cell line is especially prone to SOICR and calcium release through the defective RyR2 channel was measured with a calcium-sensitive fluorescent dye. Results revealed that the 4'-hydroxy derivative is slightly more effective than carvedilol in suppressing SOICR.
Unknown
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:59:52 UTC 2021
Edited
by admin
on Fri Jun 25 22:59:52 UTC 2021
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
FDA UNII
I02L7A715Z
Created by admin on Fri Jun 25 22:59:52 UTC 2021 , Edited by admin on Fri Jun 25 22:59:52 UTC 2021
PRIMARY
EPA CompTox
142227-49-4
Created by admin on Fri Jun 25 22:59:52 UTC 2021 , Edited by admin on Fri Jun 25 22:59:52 UTC 2021
PRIMARY
CAS
142227-49-4
Created by admin on Fri Jun 25 22:59:52 UTC 2021 , Edited by admin on Fri Jun 25 22:59:52 UTC 2021
PRIMARY
PUBCHEM
4572774
Created by admin on Fri Jun 25 22:59:52 UTC 2021 , Edited by admin on Fri Jun 25 22:59:52 UTC 2021
PRIMARY
Related Record Type Details
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