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Details

Stereochemistry RACEMIC
Molecular Formula C18H28N2O4
Molecular Weight 336.4259
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACEBUTOLOL

SMILES

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

InChI

InChIKey=GOEMGAFJFRBGGG-UHFFFAOYSA-N
InChI=1S/C18H28N2O4/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)

HIDE SMILES / InChI
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
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
Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography.
2001 Apr 6
Evidence towards the role of arylamine N-acetyltransferase in Mycobacterium smegmatis and development of a specific antiserum against the homologous enzyme of Mycobacterium tuberculosis.
2001 Dec
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product.
2001 Feb
Influence of carvedilol on the benefits of physical training in patients with moderate chronic heart failure.
2001 Jun
beta(1)-adrenergic antagonists improve sleep and behavioural disturbances in a circadian disorder, Smith-Magenis syndrome.
2001 Sep
Isolation and properties of genetically defined strains of the methylotrophic yeast Hansenula polymorpha CBS4732.
2002 Feb
Mutations of muscle glycogen synthase that disable activation by glucose 6-phosphate.
2002 Jan 15
Propranolol and metoprolol enhance the anticonvulsant action of valproate and diazepam against maximal electroshock.
2002 Jan-Feb
Efflux ratio cannot assess P-glycoprotein-mediated attenuation of absorptive transport: asymmetric effect of P-glycoprotein on absorptive and secretory transport across Caco-2 cell monolayers.
2003 Aug
Changes in serum lipids and antioxidant status in west Algerian patients with essential hypertension treated with acebutolol compared to healthy subjects.
2003 Aug
Evaluation of teicoplanin chiral stationary phases of 3.5 and 5 microm inside diameter silica microparticles by polar-organic mode capillary electrochromatography.
2003 Sep
Spectrophotometric determination of some beta-blockers in dosage forms based on complex formation with Cu(II) and Co(II).
2004 Jun
[Cholinergic urticaria revealed by beta-blockers: case report and therapeutic management].
2005 Nov-Dec
Transport of acebutolol through rabbit corneal epithelium.
2006 Apr
Spectrophotometric and spectrofluorimetric methods for analysis of tramadol, acebutolol and dothiepin in pharmaceutical preparations.
2006 Dec
Transdermal delivery of beta-blockers.
2006 May
Stability of chosen beta-adrenolytic drugs of different polarity in basic environment.
2008 Mar-Apr
First record of Prorocentrum lima (Dinophyceae) inside harbor areas and along the Abruzzo region coast, W Adriatic.
2009 Apr
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
The role of transporters in the pharmacokinetics of orally administered drugs.
2009 Sep
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.
Name Type Language
C07AB04
Preferred Name English
ACEBUTOLOL
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
Acebutolol [WHO-DD]
Common Name English
BUTANAMIDE, N-(3-ACETYL-4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, (±)-
Systematic Name English
acebutolol [INN]
Common Name English
ACEBUTOLOL [VANDF]
Common Name English
ACEBUTOLOL [MI]
Common Name English
ACEBUTOLOL [USAN]
Common Name English
ACEBUTOLOL [MART.]
Common Name English
(±)-3'-ACETYL-4'-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)BUTYRANILIDE
Systematic Name English
Classification Tree Code System Code
WHO-ATC C07AB04
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
NDF-RT N0000175556
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
NDF-RT N0000000161
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
WHO-VATC QC07AB04
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
LIVERTOX NBK548853
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
WHO-ATC C07BB04
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
NCI_THESAURUS C29576
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
Code System Code Type Description
INN
3295
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
MESH
D000070
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
NCI_THESAURUS
C61525
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
PUBCHEM
1978
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
DAILYMED
67P356D8GH
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
ECHA (EC/EINECS)
253-539-0
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
DRUG BANK
DB01193
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
SMS_ID
100000092351
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
RXCUI
149
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY RxNorm
EVMPD
SUB07371MIG
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
MERCK INDEX
m1290
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY Merck Index
LACTMED
Acebutolol
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
FDA UNII
67P356D8GH
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
CHEBI
2379
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID2048539
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
CAS
37517-30-9
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
ChEMBL
CHEMBL642
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
DRUG CENTRAL
40
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
WIKIPEDIA
ACEBUTOLOL
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY
IUPHAR
7107
Created by admin on Mon Mar 31 18:50:06 GMT 2025 , Edited by admin on Mon Mar 31 18:50:06 GMT 2025
PRIMARY