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Details

Stereochemistry RACEMIC
Molecular Formula C16H24N2O4
Molecular Weight 308.3734
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIACETOLOL

SMILES

CC(C)NCC(COc1ccc(cc1C(=O)C)N=C(C)O)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)

HIDE SMILES / InChI

Molecular Formula C16H24N2O4
Molecular Weight 308.3734
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

PubMed

TitleDatePubMed
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
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection.
2004 Apr 20
Effects of grapefruit juice on the pharmacokinetics of acebutolol.
2005 Dec

Sample Use Guides

Daily dosage - 200 to 800 mg (two tablets being administered twice a day)
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:02:51 UTC 2021
Edited
by admin
on Sat Jun 26 16:02:51 UTC 2021
Record UNII
4ER0CZ5G7C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIACETOLOL
INN   WHO-DD  
INN  
Official Name English
DIACETOLOL [WHO-DD]
Common Name English
ACEBUTOLOL RELATED COMPOUND B
USP-RS  
Common Name English
ACEBUTOLOL RELATED COMPOUND B [USP-RS]
Common Name English
(+/-)-3'-ACETYL-4'-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)ACETANILIDE
Systematic Name English
ACEBUTOLOL RELATED COMPOUND B [USP]
Common Name English
DIACETOLOL [INN]
Common Name English
ACETAMIDE, N-(3-ACETYL-4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, (+/-)
Common Name English
Code System Code Type Description
FDA UNII
4ER0CZ5G7C
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
NCI_THESAURUS
C166754
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
USP_CATALOG
1000623
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY USP-RS
PUBCHEM
50894
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
MESH
C025527
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
INN
4662
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-088-3
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
CAS
22568-64-5
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
EVMPD
SUB07062MIG
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
WIKIPEDIA
DIACETOLOL
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL2110821
Created by admin on Sat Jun 26 16:02:52 UTC 2021 , Edited by admin on Sat Jun 26 16:02:52 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE ACTIVE
MAJOR
PLASMA; URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY