Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H24N2O4 |
Molecular Weight | 308.3728 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1C(C)=O
InChI
InChIKey=AWOGXJOBNAWQSF-UHFFFAOYSA-N
InChI=1S/C16H24N2O4/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)
Molecular Formula | C16H24N2O4 |
Molecular Weight | 308.3728 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
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Pharmacological properties of diacetolol (M & B 16,942), a major metabolite of acebutolol. | 1982 May 7 |
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Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites. | 2000 Apr |
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Pharmacokinetics of acebutolol and its main metabolite, diacetolol after oral administration of acebutolol in rabbits with carbon tetrachloride-induced hepatic failure. | 2002 Aug |
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Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection. | 2004 Apr 20 |
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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 |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:41:56 GMT 2025
by
admin
on
Mon Mar 31 18:41:56 GMT 2025
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Record UNII |
4ER0CZ5G7C
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Record Status |
Validated (UNII)
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4ER0CZ5G7C
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C166754
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SUB07062MIG
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DIACETOLOL
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CHEMBL2110821
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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |