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
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26584883
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 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.
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DTXSID40404402
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4572774
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PARENT (METABOLITE ACTIVE)
SUBSTANCE RECORD
