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Details

Stereochemistry RACEMIC
Molecular Formula C16H24N2O4.ClH
Molecular Weight 344.8343
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIACETOLOL HYDROCHLORIDE

SMILES

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

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

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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

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 03:54:21 UTC 2021
Edited
by admin
on Sat Jun 26 03:54:21 UTC 2021
Record UNII
GN9199S55X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIACETOLOL HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
ACETAMIDE, N-(3-ACETYL-4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, MONOHYDROCHLORIDE, (+/-)-
Common Name English
DIACETOLOL HCL
Common Name English
DIACETOLOL HYDROCHLORIDE [WHO-DD]
Common Name English
NSC-326057
Code English
M&B-16942A
Code English
(+/-)-3'-ACETYL-4'-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)ACETANILIDE MONOHYDROCHLORIDE
Systematic Name English
EU-4891
Code English
DIACETOLOL HYDROCHLORIDE [USAN]
Common Name English
M&B 16942A
Code English
Code System Code Type Description
PUBCHEM
50893
Created by admin on Sat Jun 26 03:54:21 UTC 2021 , Edited by admin on Sat Jun 26 03:54:21 UTC 2021
PRIMARY
NCI_THESAURUS
C169904
Created by admin on Sat Jun 26 03:54:21 UTC 2021 , Edited by admin on Sat Jun 26 03:54:21 UTC 2021
PRIMARY
CAS
69796-04-9
Created by admin on Sat Jun 26 03:54:21 UTC 2021 , Edited by admin on Sat Jun 26 03:54:21 UTC 2021
PRIMARY
FDA UNII
GN9199S55X
Created by admin on Sat Jun 26 03:54:21 UTC 2021 , Edited by admin on Sat Jun 26 03:54:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL2110821
Created by admin on Sat Jun 26 03:54:21 UTC 2021 , Edited by admin on Sat Jun 26 03:54:21 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY