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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
Structure of DIACETOLOL HYDROCHLORIDE

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

HIDE SMILES / InChI
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
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection.
2004 Apr 20

Sample Use Guides

Daily dosage - 200 to 800 mg (two tablets being administered twice a day)
Route of Administration: Oral
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
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
Diacetolol hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
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
NCI_THESAURUS
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
CAS
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
FDA UNII
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
NSC
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
ChEMBL
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