Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H24N2O4.ClH |
Molecular Weight | 344.834 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)NCC(O)COC1=C(C=C(NC(C)=O)C=C1)C(C)=O
InChI
InChIKey=RRLYGXRMVLYFNX-UHFFFAOYSA-N
InChI=1S/C16H24N2O4.ClH/c1-10(2)17-8-14(21)9-22-16-6-5-13(18-12(4)20)7-15(16)11(3)19;/h5-7,10,14,17,21H,8-9H2,1-4H3,(H,18,20);1H
Diacetolol is the major metabolite of the β-adrenoceptor blocking agent, acebutolol. In vitro, the β-adrenoceptor blocking potency of diacetolol was less than that of acebutolol but its cardioselectivity (atrial relative to tracheal tissue) was greater. Diacetolol had weak intrinsic sympathomimetic activity, and no significant membrane-stabilizing activity. It did not restore sinus rhythm to anaesthetized dogs with ouabain-induced arrhythmias but was similar to acebutolol in preventing arrhythmia induced by adrenaline/methylchloroform in anaesthetized cats. Study of diacetolol pharmacokinetics and bioavailability suggests either a first-pass effect or incomplete absorption of diacetolol after oral administration. Diacetolol plasma half-life after oral administration is about 12 h and is not dose-dependent. Diacetolol possesses significant antihypertensive action against moderate essential hypertension in man. Its antihypertensive effect is associated with a reduction in the heart rate and a decrease in plasma renin activity.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacological properties of diacetolol (M & B 16,942), a major metabolite of acebutolol. | 1982 May 7 |
|
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites. | 2000 Apr |
|
Pharmacokinetics of acebutolol and its main metabolite, diacetolol after oral administration of acebutolol in rabbits with carbon tetrachloride-induced hepatic failure. | 2002 Aug |
|
Influence of cimetidine co-administration on the pharmacokinetics of acebutolol enantiomers and its metabolite diacetolol in a rat model: the effect of gastric pH on double-peak phenomena. | 2003 Apr 14 |
|
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection. | 2004 Apr 20 |
|
Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization. | 2004 Nov 26 |
|
Effects of grapefruit juice on the pharmacokinetics of acebutolol. | 2005 Dec |
|
Using supported liquid extraction together with cellobiohydrolase chiral stationary phases-based liquid chromatography with tandem mass spectrometry for enantioselective determination of acebutolol and its active metabolite diacetolol in spiked human plasma. | 2009 Jan 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6121577
Daily dosage - 200 to 800 mg (two tablets being administered twice a day)
Route of Administration:
Oral
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
50893
Created by
admin on Fri Dec 15 15:00:04 GMT 2023 , Edited by admin on Fri Dec 15 15:00:04 GMT 2023
|
PRIMARY | |||
|
C169904
Created by
admin on Fri Dec 15 15:00:04 GMT 2023 , Edited by admin on Fri Dec 15 15:00:04 GMT 2023
|
PRIMARY | |||
|
69796-04-9
Created by
admin on Fri Dec 15 15:00:04 GMT 2023 , Edited by admin on Fri Dec 15 15:00:04 GMT 2023
|
PRIMARY | |||
|
GN9199S55X
Created by
admin on Fri Dec 15 15:00:04 GMT 2023 , Edited by admin on Fri Dec 15 15:00:04 GMT 2023
|
PRIMARY | |||
|
326057
Created by
admin on Fri Dec 15 15:00:04 GMT 2023 , Edited by admin on Fri Dec 15 15:00:04 GMT 2023
|
PRIMARY | |||
|
CHEMBL2110821
Created by
admin on Fri Dec 15 15:00:04 GMT 2023 , Edited by admin on Fri Dec 15 15:00:04 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD