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

Details

Stereochemistry RACEMIC
Molecular Formula C18H28N2O4
Molecular Weight 336.4266
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACEBUTOLOL

SMILES

CCCC(=Nc1ccc(c(c1)C(=O)C)OCC(CNC(C)C)O)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

Molecular Formula C18H28N2O4
Molecular Weight 336.4266
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
Acebutolol-induced ventricular tachycardia reversed with sodium bicarbonate.
1999
Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography.
2001 Apr 6
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product.
2001 Feb
Isolation and properties of genetically defined strains of the methylotrophic yeast Hansenula polymorpha CBS4732.
2002 Feb
[Acebutolol in the treatment of arterial hypertension in pregnancy--comparison with commonly used hypertensive agents].
2002 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
Nodal and BMP2/4 signaling organizes the oral-aboral axis of the sea urchin embryo.
2004 Mar
Treatment of high blood pressure and gain in event-free life expectancy.
2005
Assay of acebutolol in pharmaceuticals by analytical capillary isotachophoresis.
2005 Jul 15
Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia.
2005 Oct
Acebutolol-induced subacute cutaneous lupus erythematosus.
2005 Sep-Oct
Spectrofluorimetric determination of drugs containing active methylene group using N1-methyl nicotinamide chloride as a fluorigenic agent.
2006 Jul
Abstracts of papers presented at the 2007 pittsburgh conference.
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
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007 Oct 16
Simultaneous determination of beta-blockers in human plasma using liquid chromatography-tandem mass spectrometry.
2008 Jul
Ozonation of reverse osmosis concentrate: kinetics and efficiency of beta blocker oxidation.
2008 Jun
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
Comparison of the analysis of beta-blockers by different techniques.
2009 Dec 1
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 Feb
Pharmaceutical cleaning validation using non-proximate large-area desorption electrospray ionization mass spectrometry.
2009 Jan
Determination of selected beta-receptor antagonists in biological samples by solid-phase extraction with cholesterolic phase and LC/MS.
2009 Jan
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 Jan 15
Involvement of influx and efflux transport systems in gastrointestinal absorption of celiprolol.
2009 Jul
Beta-blocking agent for treatment of infantile hemangioma.
2009 Jun
Application of ionic liquids in high performance reversed-phase chromatography.
2009 Jun 4
[Beta blockers in migraine prophylaxis].
2009 Oct
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
Medicinal chemistry of drugs used in diabetic cardiomyopathy.
2010
Management of infantile subglottic hemangioma: acebutolol or propranolol?
2010 Aug
Fate of beta blockers in aquatic-sediment systems: sorption and biotransformation.
2010 Feb 1
Correlation effect of EGFR and CXCR4 and CCR7 chemokine receptors in predicting breast cancer metastasis and prognosis.
2010 Feb 24
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
Seasonal variations in the occurrence and fate of basic and neutral pharmaceuticals in a Swedish river-lake system.
2010 Jun
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 Sat Jun 26 12:36:14 UTC 2021
Edited
by admin
on Sat Jun 26 12:36:14 UTC 2021
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
BUTANAMIDE, N-(3-ACETYL-4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, (+/-)-
Systematic Name English
ACEBUTOLOL HYDROCHLORIDE IMPURITY B [EP]
Common Name English
ACEBUTOLOL [INN]
Common Name English
ACEBUTOLOL [VANDF]
Common Name English
ACEBUTOLOL [MI]
Common Name English
ACEBUTOLOL [WHO-DD]
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 Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
NDF-RT N0000175556
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
NDF-RT N0000000161
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
WHO-VATC QC07AB04
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
LIVERTOX 7
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
WHO-ATC C07BB04
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
Code System Code Type Description
INN
3295
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
MESH
D000070
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
NCI_THESAURUS
C61525
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
PUBCHEM
1978
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
ECHA (EC/EINECS)
253-539-0
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
DRUG BANK
DB01193
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
RXCUI
149
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY RxNorm
EVMPD
SUB07371MIG
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
MERCK INDEX
M1290
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY Merck Index
LACTMED
Acebutolol
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
FDA UNII
67P356D8GH
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
EPA CompTox
37517-30-9
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
CAS
37517-30-9
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
ChEMBL
CHEMBL642
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
DRUG CENTRAL
40
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
WIKIPEDIA
ACEBUTOLOL
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
IUPHAR
7107
Created by admin on Sat Jun 26 12:36:15 UTC 2021 , Edited by admin on Sat Jun 26 12:36:15 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
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METABOLITE -> PARENT
PLASMA; URINE
METABOLITE ACTIVE -> PARENT
MAJOR
PLASMA; URINE
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC