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

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

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

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
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product.
2001 Feb
[Interaction between melilot and acenocoumarol? (Melilotruscus aculeatus)].
2001 May-Jun
beta(1)-adrenergic antagonists improve sleep and behavioural disturbances in a circadian disorder, Smith-Magenis syndrome.
2001 Sep
Pharmacokinetics of acebutolol and its main metabolite, diacetolol after oral administration of acebutolol in rabbits with carbon tetrachloride-induced hepatic failure.
2002 Aug
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
Electrocardiographic changes associated with beta-blocker toxicity.
2002 Dec
[Acute poisoning with nifedipine and acebutol: two cases].
2003
Sleep-deprived mice show altered cytokine production manifest by perturbations in serum IL-1ra, TNFa, and IL-6 levels.
2003 Dec
Evaluation of an immortalized retinal endothelial cell line as an in vitro model for drug transport studies across the blood-retinal barrier.
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
Medication error caused by confusing drug blisters.
2004 Jun 26
Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia.
2005 Oct
Stability of atenolol, acebutolol and propranolol in acidic environment depending on its diversified polarity.
2006
Evaluation of chromatographic descriptors for the prediction of gastro-intestinal absorption of drugs.
2007 Jan 5
Determination of beta-blockers and beta2-agonists in sewage by solid-phase extraction and liquid chromatography-tandem mass spectrometry.
2007 May 4
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007 Oct 16
Stability of chosen beta-adrenolytic drugs of different polarity in basic environment.
2008 Mar-Apr
Beta-blocking agent for treatment of infantile hemangioma.
2009 Jun
Application of ionic liquids in high performance reversed-phase chromatography.
2009 Jun 4
The role of transporters in the pharmacokinetics of orally administered drugs.
2009 Sep
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
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 Thu Jul 06 00:58:37 UTC 2023
Edited
by admin
on Thu Jul 06 00:58:37 UTC 2023
Record UNII
67P356D8GH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACEBUTOLOL
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
C07AB04
Code 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 Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
NDF-RT N0000175556
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
NDF-RT N0000000161
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
WHO-VATC QC07AB04
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
LIVERTOX NBK548853
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
WHO-ATC C07BB04
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
NCI_THESAURUS C29576
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
Code System Code Type Description
INN
3295
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
MESH
D000070
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
NCI_THESAURUS
C61525
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
PUBCHEM
1978
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
DAILYMED
67P356D8GH
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
253-539-0
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
DRUG BANK
DB01193
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
SMS_ID
100000092351
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
RXCUI
149
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY RxNorm
EVMPD
SUB07371MIG
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
MERCK INDEX
M1290
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY Merck Index
LACTMED
Acebutolol
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
FDA UNII
67P356D8GH
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
CHEBI
2379
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID2048539
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
CAS
37517-30-9
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL642
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
DRUG CENTRAL
40
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
WIKIPEDIA
ACEBUTOLOL
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
IUPHAR
7107
Created by admin on Thu Jul 06 00:58:37 UTC 2023 , Edited by admin on Thu Jul 06 00:58:37 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
TARGET -> AGONIST
SHORT-ACTING
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METABOLITE -> PARENT
PLASMA; URINE
METABOLITE ACTIVE -> PARENT
MAJOR
PLASMA; URINE
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC