Page last updated: 2024-12-06

diacetolol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

diacetolol: RN given refers to parent cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	50894
CHEMBL ID	2110821
SCHEMBL ID	828479
MeSH ID	M0084991

Synonyms (45)

Synonym
acetanilide, 3'-acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)-, dl-
einecs 245-088-3
(1)-n-(3-acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)acetamide
brn 2156350
diacetololum [inn-latin]
diacetolol
m and b 16942
diacetolol [inn:ban]
acetylacebutolol
acetamide, n-(3-acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)-, (+-)-
(+-)-diacetolol
(+-)-n-(3-acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)acetamide
dl-1-(2-acetyl-4-acetamidophenoxy)-2-hydroxy-3-isopropylaminopropane
(rs)-1-(2-acetyl-4-acetamidophenoxy)-2-hydroxy-3-isopropylaminopropane
FT-0666315
n-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
28197-69-5
unii-4er0cz5g7c
22568-64-5
4er0cz5g7c ,
diacetololum
rac diacetolol
(+/-)-3'-acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)acetanilide
diacetolol [inn]
diacetolol [who-dd]
acebutolol hydrochloride impurity b [ep impurity]
n-(3-acetyl-4-((2rs)-2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)acetamide
n-(3-acetyl-4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide
acetamide, n-(3-acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)-, (+/-)-
SCHEMBL828479
CHEMBL2110821
AKOS027288882
n-(3-acetyl-4-(2-hydroxy-3-(isopropylamino)-propoxy)phenyl)acetamide
Q5270217
E76509
(+/-)-n-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]acetamide
acetamide,n-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]-,(?-
acebutolol impurity b
(+/-)-diacetolol
DTXSID70865421
CS-0019867
n-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
EN300-18166916
Z2037280151
HY-100635

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
" Acebutolol is as effective as other beta-blocking agents, and in a large, double-blind, parallel study against propranolol was found to cause less reduction in heart rate, and fewer neurologic side effects and patient withdrawals due to adverse effects."	( Acebutolol: a review of its pharmacology, pharmacokinetics, clinical uses, and adverse effects. Singh, BN; Thoden, WR; Wahl, J, )	0.13

Pharmacokinetics

Excerpt	Reference	Relevance
" Furthermore, the effect of cimetidine (CIM) on pharmacokinetic parameters of AC and its metabolite diacetolol (DC) was evaluated."	( 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. Foster, RT; Mostafavi, SA, 2003)	0.75

Bioavailability

Excerpt	Reference	Relevance
"The pharmacokinetics and bioavailability of diacetolol, the principal metabolite of acebutolol, were studied in 6 healthy subjects."	( Pharmacokinetics and bioavailability of diacetolol, the main metabolite of acebutolol. Andre-Fouet, X; Chau, NP; Flouvat, B; Gregoire, J; Roux, A; Viallet, M; Woehrle, R, 1981)	0.79

Dosage Studied

Excerpt	Relevance	Reference
" Evaluation of the iatrogenic risk shows that pharmacologically active amounts of acebutolol might be received by a neonate if the daily maternal dosage exceeds 400 mg/day and/or renal function in the mother is impaired."	( To nurse when receiving acebutolol: is it dangerous for the neonate? Bianchetti, G; Boutroy, MJ; Dubruc, C; Morselli, PL; Vert, P, 1986)	0.27
" When applied to the assay of biological fluids collected during single and chronic oral dosing with acebutolol (Sectral), this procedure failed to reveal any important stereoselectivity in the disposition of either acebutolol or diacetolol in man."	( Preliminary study of the disposition in man of acebutolol and its metabolite, diacetolol, using a new stereoselective hplc method. Gulaid, A; Kaye, CM; Sankey, MG, 1984)	0.68

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (4)

Assay ID	Title	Year	Journal	Article
AID1147037	Antiarrhythmic activity in iv dosed dog assessed as dose required for reversal of ouabain-induced cardiac arrhythmia	1976	Journal of medicinal chemistry, Mar, Volume: 19, Issue:3	A new series of cardioselective adrenergic beta-receptor blocking compounds. 1-(2-Acyl-4-acylaminophenoxy)-3-isopropylaminopropan-2-ols.
AID1147034	In vivo beta-1 adrenergic receptor blocking activity in iv dosed cat assessed as half dose required for desensitizing isoproterenol-induced tachycardia after 3.5 mins	1976	Journal of medicinal chemistry, Mar, Volume: 19, Issue:3	A new series of cardioselective adrenergic beta-receptor blocking compounds. 1-(2-Acyl-4-acylaminophenoxy)-3-isopropylaminopropan-2-ols.
AID1147036	Ratio of in vivo beta-2 adrenergic receptor blocking activity in iv dosed cat assessed as half dose required for desensitizing isoproterenol-induced diastolic hypotensive response to in vivo beta-1 adrenergic receptor blocking activity in iv dosed cat ass	1976	Journal of medicinal chemistry, Mar, Volume: 19, Issue:3	A new series of cardioselective adrenergic beta-receptor blocking compounds. 1-(2-Acyl-4-acylaminophenoxy)-3-isopropylaminopropan-2-ols.
AID1147035	In vivo beta-2 adrenergic receptor blocking activity in iv dosed cat assessed as half dose required for desensitizing isoproterenol-induced diastolic hypotensive response after 3.5 mins	1976	Journal of medicinal chemistry, Mar, Volume: 19, Issue:3	A new series of cardioselective adrenergic beta-receptor blocking compounds. 1-(2-Acyl-4-acylaminophenoxy)-3-isopropylaminopropan-2-ols.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	28 (70.00)	18.7374
1990's	6 (15.00)	18.2507
2000's	4 (10.00)	29.6817
2010's	1 (2.50)	24.3611
2020's	1 (2.50)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.69

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	20.69 (24.57)
Research Supply Index	4.03 (2.92)
Research Growth Index	4.13 (4.65)
Search Engine Demand Index	21.17 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (20.69)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	9 (19.57%)	5.53%
Reviews	2 (4.35%)	6.00%
Case Studies	1 (2.17%)	4.05%
Observational	0 (0.00%)	0.25%
Other	34 (73.91%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	9.31	40	8	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
alprenolol Alprenolol: One of the ADRENERGIC BETA-ANTAGONISTS used as an antihypertensive, anti-anginal, and anti-arrhythmic agent.. alprenolol : A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.	6.96	1	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	7.01	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	3.76	2	1	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	8.35	1	1	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	3.34	1	1	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
practolol Practolol: A beta-1 adrenergic antagonist that has been used in the emergency treatment of CARDIAC ARRYTHMIAS.. practolol : N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythmias.	1.95	1	0	acetamides; ethanolamines; propanolamine; secondary alcohol; secondary amino compound	anti-arrhythmia drug; beta-adrenergic antagonist
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	9.84	4	2	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
sotalol Sotalol: An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.. sotalol : A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.	1.96	1	0	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	1.96	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
dihydroalprenolol Dihydroalprenolol: Hydrogenated alprenolol derivative where the extra hydrogens are often tritiated. This radiolabeled form of ALPRENOLOL, a beta-adrenergic blocker, is used to label the beta-adrenergic receptor for isolation and study.	6.96	1	0
carazolol carazolol: RN given refers to parent cpd without isomeric designation; structure	2.21	1	0	carbazoles
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	1.96	1	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	1.96	1	0	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies	Trials
Arrhythmia [description not available]	5.18	4	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	5.18	4	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.05	1	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	2.01	1	0
Hepatic Failure [description not available]	7.01	1	0
Liver Failure Severe inability of the LIVER to perform its normal metabolic functions, as evidenced by severe JAUNDICE and abnormal serum levels of AMMONIA; BILIRUBIN; ALKALINE PHOSPHATASE; ASPARTATE AMINOTRANSFERASE; LACTATE DEHYDROGENASES; and albumin/globulin ratio. (Blakiston's Gould Medical Dictionary, 4th ed)	2.01	1	0
Blood Pressure, High [description not available]	5.65	7	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	10.65	7	1
Angor Pectoris [description not available]	3.34	1	1
Angina Pectoris The symptom of paroxysmal pain consequent to MYOCARDIAL ISCHEMIA usually of distinctive character, location and radiation. It is thought to be provoked by a transient stressful situation during which the oxygen requirements of the MYOCARDIUM exceed that supplied by the CORONARY CIRCULATION.	3.34	1	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	3.57	3	0
Adjuvant Arthritis [description not available]	1.98	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	1.98	1	0
Liver Dysfunction [description not available]	2.88	1	0
Liver Diseases Pathological processes of the LIVER.	2.88	1	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	1.96	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.96	1	0
Complication, Intraoperative [description not available]	3.35	1	1

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