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(OCC(O)CNC(C)C)C(=C1)C(C)=O

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

1984
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

1984
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 24
Sex: M
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
Health Status: unhealthy
Age Group: 31-63
Sex: M+F
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
Health Status: healthy
Age Group: 43
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 16
Sex: F
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
Health Status: healthy
Age Group: 24
Sex: M
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
Health Status: healthy
Age Group: 24
Sex: M
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
Health Status: healthy
Age Group: 24
Sex: M
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
Health Status: healthy
Age Group: 24
Sex: M
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
Health Status: unhealthy
Age Group: 31-63
Sex: M+F
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
Health Status: healthy
Age Group: 43
Sex: F
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
Health Status: healthy
Age Group: 43
Sex: F
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
Health Status: healthy
Age Group: 43
Sex: F
Sources:
PubMed

PubMed

TitleDatePubMed
Potential for biodegradation and sorption of acetaminophen, caffeine, propranolol and acebutolol in lab-scale aqueous environments.
2010-11-15
Occurrence and removal of estrogens and beta blockers by various processes in wastewater treatment plants.
2010-09-01
Management of infantile subglottic hemangioma: acebutolol or propranolol?
2010-08
Principal component analysis of HPLC retention data and molecular modeling structural parameters of cardiovascular system drugs in view of their pharmacological activity.
2010-07-09
Seasonal variations in the occurrence and fate of basic and neutral pharmaceuticals in a Swedish river-lake system.
2010-06
Correlation effect of EGFR and CXCR4 and CCR7 chemokine receptors in predicting breast cancer metastasis and prognosis.
2010-02-24
Fate of beta blockers in aquatic-sediment systems: sorption and biotransformation.
2010-02-01
Medicinal chemistry of drugs used in diabetic cardiomyopathy.
2010
Comparison of the analysis of beta-blockers by different techniques.
2009-12-01
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009-10-02
[Beta blockers in migraine prophylaxis].
2009-10
The role of transporters in the pharmacokinetics of orally administered drugs.
2009-09
Involvement of influx and efflux transport systems in gastrointestinal absorption of celiprolol.
2009-07
Application of ionic liquids in high performance reversed-phase chromatography.
2009-06-04
Beta-blocking agent for treatment of infantile hemangioma.
2009-06
First record of Prorocentrum lima (Dinophyceae) inside harbor areas and along the Abruzzo region coast, W Adriatic.
2009-04
In-vitro relationship between protein-binding and free drug concentrations of a water-soluble selective beta-adrenoreceptor antagonist (atenolol) and its interaction with arsenic.
2009-02
Using supported liquid extraction together with cellobiohydrolase chiral stationary phases-based liquid chromatography with tandem mass spectrometry for enantioselective determination of acebutolol and its active metabolite diacetolol in spiked human plasma.
2009-01-15
Pharmaceutical cleaning validation using non-proximate large-area desorption electrospray ionization mass spectrometry.
2009-01
Determination of selected beta-receptor antagonists in biological samples by solid-phase extraction with cholesterolic phase and LC/MS.
2009-01
Simultaneous determination of beta-blockers in human plasma using liquid chromatography-tandem mass spectrometry.
2008-07
Ozonation of reverse osmosis concentrate: kinetics and efficiency of beta blocker oxidation.
2008-06
Stability of chosen beta-adrenolytic drugs of different polarity in basic environment.
2008-05-15
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007-10-16
Evaluation of the impact on entomocoenosis of active agents allowed in organic olive farming against Bactrocera oleae (Gmelin, 1790).
2007-09-01
Cutaneous vasculitis induced by carvedilol.
2007-08
Biopharmaceutics classification of selected beta-blockers: solubility and permeability class membership.
2007-07-20
Amoxicillin-Induced Eosinophilic Pneumonia with Granulomatous Reaction: Discrepancy between Drug-Induced Lymphocyte Stimulation Test Findings and the Provocation Drug Test.
2007-06-15
Determination of beta-blockers and beta2-agonists in sewage by solid-phase extraction and liquid chromatography-tandem mass spectrometry.
2007-05-04
Antihypertensive and antioxidant action of amlodipine and vitamin C in patients of essential hypertension.
2007-03
Elimination of pharmaceuticals in sewage treatment plants in Finland.
2007-03
A population-based analysis of the class effect of beta-blockers after myocardial infarction.
2007-02
Evaluation of chromatographic descriptors for the prediction of gastro-intestinal absorption of drugs.
2007-01-05
Spectrophotometric and spectrofluorimetric methods for analysis of acyclovir and acebutolol hydrochloride.
2007-01
Abstracts of papers presented at the 2007 pittsburgh conference.
2007
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
[Interrelationship between changes of rate and variability of cardiac rhythm under influence of beta-adrenoblockers].
2007
Clinical review: aggressive management and extracorporeal support for drug-induced cardiotoxicity.
2007
Spectrophotometric and spectrofluorimetric methods for analysis of tramadol, acebutolol and dothiepin in pharmaceutical preparations.
2006-12
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.
2006-11-17
Spectrophotometric and spectrofluorimetric methods for analysis of acyclovir and acebutolol hydrochloride.
2006-11
Arrhythmogenic right ventricular dysplasia in pregnancy: a case report.
2006-09
Smith-Magenis syndrome: a case report of improved sleep after treatment with beta1-adrenergic antagonists and melatonin.
2006-09
Spectrofluorimetric determination of drugs containing active methylene group using N1-methyl nicotinamide chloride as a fluorigenic agent.
2006-07
Transdermal delivery of beta-blockers.
2006-05
Transport of acebutolol through rabbit corneal epithelium.
2006-04
[Cholinergic urticaria revealed by beta-blockers: case report and therapeutic management].
2006-03-25
UPLC/MS for the identification of beta-blockers.
2006-02-24
Stability of atenolol, acebutolol and propranolol in acidic environment depending on its diversified polarity.
2006
Treatment of high blood pressure and gain in event-free life expectancy.
2005
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 Mon Mar 31 18:03:13 GMT 2025
Edited
by admin
on Mon Mar 31 18:03:13 GMT 2025
Record UNII
B025Y34C54
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETANOL
Preferred Name English
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
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 Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
EU-Orphan Drug EU/3/16/1742
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
251-980-3
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
PUBCHEM
36816
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
SMS_ID
100000091380
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID5045461
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL642
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
RXCUI
142130
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C28806
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
HSDB
6524
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
CHEBI
2380
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
FDA UNII
B025Y34C54
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
DRUG BANK
DBSALT000192
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
RS_ITEM_NUM
1000601
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
CAS
34381-68-5
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
NSC
757412
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
DAILYMED
B025Y34C54
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
EVMPD
SUB00240MIG
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY
MERCK INDEX
m1290
Created by admin on Mon Mar 31 18:03:13 GMT 2025 , Edited by admin on Mon Mar 31 18:03:13 GMT 2025
PRIMARY Merck Index
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