U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H28N2O4.ClH
Molecular Weight 372.887
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACEBUTOLOL HYDROCHLORIDE

SMILES

Cl.CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1

InChI

InChIKey=KTUFKADDDORSSI-UHFFFAOYSA-N
InChI=1S/C18H28N2O4.ClH/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3;/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H28N2O4
Molecular Weight 336.4259
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Acebutolol is a cardioselective, beta-adrenoreceptor blocking agent, which possesses mild intrinsic sympathomimetic activity (ISA) in its therapeutically effective dose range. Acebutolol is marketed under the trade names Sectral, Prent. Acebutolol is indicated for the management of hypertension in adults. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. Acebutolol is also indicated in the management of ventricular premature beats; it reduces the total number of premature beats, as well as the number of paired and multiform ventricular ectopic beats, and R-on-T beats. Acebutolol is a selective β1-receptor antagonist. Activation of β1-receptors by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Acebutolol blocks these receptors, lowering the heart rate and blood pressure. This drug then has the reverse effect of epinephrine. In addition, beta blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels.

CNS Activity

Curator's Comment: Acebutolol is relatively hydrophilic and does not readily cross the blood-brain barrier, a fact that may be clinically significant in reducing the frequency and severity of central nervous system adverse effects.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SECTRAL

Approved Use

INDICATIONS & USAGE HYPERTENSION: Acebutolol hydrochloride capsules are indicated for the management of hypertension in adults. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. VENTRICULAR ARRHYTHMIAS: Acebutolol hydrochloride capsules are indicated in the management of ventricular premature beats; it reduces the total number of premature beats, as well as the number of paired and multiform ventricular ectopic beats, and R-on-T beats.

Launch Date

4.73039995E11
Primary
SECTRAL

Approved Use

INDICATIONS & USAGE HYPERTENSION: Acebutolol hydrochloride capsules are indicated for the management of hypertension in adults. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. VENTRICULAR ARRHYTHMIAS: Acebutolol hydrochloride capsules are indicated in the management of ventricular premature beats; it reduces the total number of premature beats, as well as the number of paired and multiform ventricular ectopic beats, and R-on-T beats.

Launch Date

4.73039995E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
92 ng/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACEBUTOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4492 ng × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACEBUTOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
unknown, oral
ACEBUTOLOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
74%
unknown, oral
ACEBUTOLOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Other AEs: Breathing shallow, Nausea...
Other AEs:
Breathing shallow
Nausea
Pulse thready
Tachycardia
Bradycardia
Asystole
Death (grade 5)
Blood pressure low
Sources:
9.2 g 1 times / day single, oral
Overdose
Dose: 9.2 g, 1 times / day
Route: oral
Route: single
Dose: 9.2 g, 1 times / day
Sources:
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: M
Population Size: 1
Sources:
Other AEs: Blood pressure low, Heart rate low...
Other AEs:
Blood pressure low
Heart rate low
Necrosis bowel
Muscle tone flaccid
Sources:
0.8 g 2 times / day multiple, oral
Highest studied dose
Dose: 0.8 g, 2 times / day
Route: oral
Route: multiple
Dose: 0.8 g, 2 times / day
Sources:
unhealthy, 31-63
n = 11
Health Status: unhealthy
Condition: hypertension
Age Group: 31-63
Sex: M+F
Population Size: 11
Sources:
Disc. AE: Antinuclear antibody...
AEs leading to
discontinuation/dose reduction:
Antinuclear antibody (3 patients)
Sources:
4 g 1 times / day single, oral
Overdose
Dose: 4 g, 1 times / day
Route: oral
Route: single
Dose: 4 g, 1 times / day
Sources:
healthy, 43
n = 1
Health Status: healthy
Age Group: 43
Sex: F
Population Size: 1
Sources:
Other AEs: Blood pressure low, Ventricular tachycardia...
Other AEs:
Blood pressure low
Ventricular tachycardia
Death (grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Asystole
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Blood pressure low
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Bradycardia
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Breathing shallow
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Nausea
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Pulse thready
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Tachycardia
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Death grade 5
6 g 1 times / day single, oral
Overdose
Dose: 6 g, 1 times / day
Route: oral
Route: single
Dose: 6 g, 1 times / day
Sources:
healthy, 16
n = 1
Health Status: healthy
Age Group: 16
Sex: F
Population Size: 1
Sources:
Blood pressure low
9.2 g 1 times / day single, oral
Overdose
Dose: 9.2 g, 1 times / day
Route: oral
Route: single
Dose: 9.2 g, 1 times / day
Sources:
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: M
Population Size: 1
Sources:
Heart rate low
9.2 g 1 times / day single, oral
Overdose
Dose: 9.2 g, 1 times / day
Route: oral
Route: single
Dose: 9.2 g, 1 times / day
Sources:
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: M
Population Size: 1
Sources:
Muscle tone flaccid
9.2 g 1 times / day single, oral
Overdose
Dose: 9.2 g, 1 times / day
Route: oral
Route: single
Dose: 9.2 g, 1 times / day
Sources:
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: M
Population Size: 1
Sources:
Necrosis bowel
9.2 g 1 times / day single, oral
Overdose
Dose: 9.2 g, 1 times / day
Route: oral
Route: single
Dose: 9.2 g, 1 times / day
Sources:
healthy, 24
n = 1
Health Status: healthy
Age Group: 24
Sex: M
Population Size: 1
Sources:
Antinuclear antibody 3 patients
Disc. AE
0.8 g 2 times / day multiple, oral
Highest studied dose
Dose: 0.8 g, 2 times / day
Route: oral
Route: multiple
Dose: 0.8 g, 2 times / day
Sources:
unhealthy, 31-63
n = 11
Health Status: unhealthy
Condition: hypertension
Age Group: 31-63
Sex: M+F
Population Size: 11
Sources:
Blood pressure low
4 g 1 times / day single, oral
Overdose
Dose: 4 g, 1 times / day
Route: oral
Route: single
Dose: 4 g, 1 times / day
Sources:
healthy, 43
n = 1
Health Status: healthy
Age Group: 43
Sex: F
Population Size: 1
Sources:
Ventricular tachycardia
4 g 1 times / day single, oral
Overdose
Dose: 4 g, 1 times / day
Route: oral
Route: single
Dose: 4 g, 1 times / day
Sources:
healthy, 43
n = 1
Health Status: healthy
Age Group: 43
Sex: F
Population Size: 1
Sources:
Death grade 5
4 g 1 times / day single, oral
Overdose
Dose: 4 g, 1 times / day
Route: oral
Route: single
Dose: 4 g, 1 times / day
Sources:
healthy, 43
n = 1
Health Status: healthy
Age Group: 43
Sex: F
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
[Pharmacology of acebutolol in animals].
1975 Dec 31
Acebutolol-induced ventricular tachycardia reversed with sodium bicarbonate.
1999
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites.
2000 Apr
[The comparison of clinical effectiveness of perindopril and acebutolol in the primary hypertension treatment].
2001
Comparison of the effect of perindopril and acebutolol on cerebral hemodynamics in hypertensive patients.
2001 Jan
Effect of lipophilicity on in vivo iontophoretic delivery. II. Beta-blockers.
2001 Jun
Influence of carvedilol on the benefits of physical training in patients with moderate chronic heart failure.
2001 Jun
[Interaction between melilot and acenocoumarol? (Melilotruscus aculeatus)].
2001 May-Jun
Beta-adrenergic blockade during severe ischemia.
2002 Dec
Beta-adrenergic-receptor blockade and myocardial ischemia: something old, something new.
2002 Dec
The effect of selective beta1-blockade on EMG signal characteristics during progressive endurance exercise.
2002 Dec
Propranolol and metoprolol enhance the anticonvulsant action of valproate and diazepam against maximal electroshock.
2002 Jan-Feb
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
Changes in serum lipids and antioxidant status in west Algerian patients with essential hypertension treated with acebutolol compared to healthy subjects.
2003 Aug
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.
2003 Aug
Beta 1-adrenergic antagonists and melatonin reset the clock and restore sleep in a circadian disorder, Smith-Magenis syndrome.
2003 Jan
Atrial fibrillation in chronic dialysis patients in the United States: risk factors for hospitalization and mortality.
2003 Jan 24
Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor.
2003 Jun
Evaluation of teicoplanin chiral stationary phases of 3.5 and 5 microm inside diameter silica microparticles by polar-organic mode capillary electrochromatography.
2003 Sep
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection.
2004 Apr 20
Spectrophotometric determination of some beta-blockers in dosage forms based on complex formation with Cu(II) and Co(II).
2004 Jun
[Antihypertensive therapy with left cardiac insufficiency].
2005 Dec
Effects of grapefruit juice on the pharmacokinetics of acebutolol.
2005 Dec
Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia.
2005 Oct
Acebutolol-induced subacute cutaneous lupus erythematosus.
2005 Sep-Oct
UPLC/MS for the identification of beta-blockers.
2006 Feb 24
Spectrophotometric and spectrofluorimetric methods for analysis of acyclovir and acebutolol hydrochloride.
2006 Nov
Analysis of neutral and basic pharmaceuticals in sewage treatment plants and in recipient rivers using solid phase extraction and liquid chromatography-tandem mass spectrometry detection.
2006 Nov 17
Smith-Magenis syndrome: a case report of improved sleep after treatment with beta1-adrenergic antagonists and melatonin.
2006 Sep
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
Cutaneous vasculitis induced by carvedilol.
2007 Aug
Biopharmaceutics classification of selected beta-blockers: solubility and permeability class membership.
2007 Jul-Aug
Amoxicillin-Induced Eosinophilic Pneumonia with Granulomatous Reaction: Discrepancy between Drug-Induced Lymphocyte Stimulation Test Findings and the Provocation Drug Test.
2007 Jun 15
Elimination of pharmaceuticals in sewage treatment plants in Finland.
2007 Mar
Simultaneous determination of beta-blockers in human plasma using liquid chromatography-tandem mass spectrometry.
2008 Jul
First record of Prorocentrum lima (Dinophyceae) inside harbor areas and along the Abruzzo region coast, W Adriatic.
2009 Apr
Comparison of the analysis of beta-blockers by different techniques.
2009 Dec 1
Application of ionic liquids in high performance reversed-phase chromatography.
2009 Jun 4
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Principal component analysis of HPLC retention data and molecular modeling structural parameters of cardiovascular system drugs in view of their pharmacological activity.
2010 Jul 9
Potential for biodegradation and sorption of acetaminophen, caffeine, propranolol and acebutolol in lab-scale aqueous environments.
2010 Nov 15
Occurrence and removal of estrogens and beta blockers by various processes in wastewater treatment plants.
2010 Sep 1
Patents

Sample Use Guides

Hypertension The initial dosage of acebutolol in uncomplicated mild-to-moderate hypertension is 400 mg. This can be given as a single daily dose, but in occasional patients twice daily dosing may be required for adequate 24-hour blood-pressure control. An optimal response is usually achieved with dosages of 400 to 800 mg per day, although some patients have been maintained on as little as 200 mg per day. Patients with more severe hypertension or who have demonstrated inadequate control may respond to a total of 1200 mg daily (administered b.i.d.), or to the addition of a second antihypertensive agent. Beta-1 selectivity diminishes as dosage is increased. Ventricular Arrhythmia The usual initial dose of acebutolol is 400 mg daily given as 200 mg b.i.d. Dosage should be increased gradually until an optimal clinical response is obtained, generally at 600 to 1200 mg per day. If treatment is to be discontinued, the dosage should be reduced gradually over a period of about two weeks. Use in Older Patients Older patients have an approximately 2-fold increase in bioavailability and may require lower maintenance doses. Doses above 800 mg/day should be avoided in the elderly.
Route of Administration: Oral
In Vitro Use Guide
Two adrenergic receptor antagonists, acebutolol and propranolol, were observed to depress rabbit heart contractile force and adrenaline-stimulated adenylate cyclase activity at 1 X 10-(5) to 1 X 10-(3) M and 1 X 10-(6) to 1 X 10-(3) M concentrations, respectively. Acebutolol depressed sarcoplasmic reticular and mitochondrial calcium uptake at 5 X 10-(3) to 10-(2) M concentrations.
Substance Class Chemical
Created
by admin
on Fri Dec 16 17:38:46 UTC 2022
Edited
by admin
on Fri Dec 16 17:38:46 UTC 2022
Record UNII
B025Y34C54
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACEBUTOLOL HYDROCHLORIDE
EP   HSDB   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
BUTANAMIDE, N-(3-ACETYL-4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, MONOHYDROCHLORIDE, (±)-
Common Name English
ACEBUTOLOL HYDROCHLORIDE [VANDF]
Common Name English
Acebutolol hydrochloride [WHO-DD]
Common Name English
ACETANOL
Brand Name English
IL-17803A
Code English
B-17803A
Code English
ACEBUTOLOL HYDROCHLORIDE [JAN]
Common Name English
M&B-17803A
Code English
ACEBUTOLOL HYDROCHLORIDE [USP IMPURITY]
Common Name English
M&B 17803A
Code English
ACEBUTOLOL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
ACEBUTOLOL HYDROCHLORIDE [USP-RS]
Common Name English
B 17803A
Code English
PRENT
Brand Name English
(±)-3'-ACETYL-4'-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)BUTYRANILIDE MONOHYDROCHLORIDE
Systematic Name English
ACEBUTOLOL HYDROCHLORIDE [HSDB]
Common Name English
ACEBUTOLOL HYDROCHLORIDE [MI]
Common Name English
N-(3-ACETYL-4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, MONOHYDROCHLORIDE, (±)-
Common Name English
ACEBUTOLOL HYDROCHLORIDE [MART.]
Common Name English
NEPTAL
Brand Name English
M&AMP
Code English
NSC-757412
Code English
ACEBUTOLOL HYDROCHLORIDE [EP IMPURITY]
Common Name English
ACEBUTOLOL HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
ACEBUTOLOL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
ACEBUTOLOL HCL
Common Name English
SECTRAL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
EU-Orphan Drug EU/3/16/1742
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
Code System Code Type Description
ECHA (EC/EINECS)
251-980-3
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
PUBCHEM
36816
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
EPA CompTox
DTXSID5045461
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
ChEMBL
CHEMBL642
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
RXCUI
142130
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY RxNorm
NCI_THESAURUS
C28806
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
HSDB
6524
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
CHEBI
2380
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
FDA UNII
B025Y34C54
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
DRUG BANK
DBSALT000192
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
RS_ITEM_NUM
1000601
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
CAS
34381-68-5
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
NSC
757412
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
DAILYMED
B025Y34C54
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
EVMPD
SUB00240MIG
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY
MERCK INDEX
M1290
Created by admin on Fri Dec 16 17:38:46 UTC 2022 , Edited by admin on Fri Dec 16 17:38:46 UTC 2022
PRIMARY Merck Index
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