Acebutolol

Identification

Summary

Acebutolol is a selective β1-receptor antagonist used for the management of hypertension and ventricular premature beats in adults.

Brand Names
Sectral
Generic Name
Acebutolol
DrugBank Accession Number
DB01193
Background

A cardioselective beta-adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm as well as weak inherent sympathomimetic action.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 336.4259
Monoisotopic: 336.204907394
Chemical Formula
C18H28N2O4
Synonyms
  • (±)-acebutolol
  • 3'-acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide
  • 5'-butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone
  • Acebutolol
  • Acebutololum
  • Acetobutolol
  • N-(3-acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide
  • N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide

Pharmacology

Indication

For the management of hypertension and ventricular premature beats in adults.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofChronic stable angina pectoris••• •••••
Management ofHypertension••• •••••
Management ofHypertension••••••••••••
Management ofVentricular arrhythmia••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Acebutolol is a cardioselective, beta-adrenoreceptor blocking agent, which possesses mild intrinsic sympathomimetic activity (ISA) in its therapeutically effective dose range. In general, beta-blockers reduce the work the heart has to do and allow it to beat more regularly. Acebutolol has less antagonistic effects on peripheral vascular ß2-receptors at rest and after epinephrine stimulation than nonselective beta-antagonists. Low doses of acebutolol produce less evidence of bronchoconstriction than nonselective agents like propranolol but more than atenolol.

Mechanism of action

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.

TargetActionsOrganism
ABeta-1 adrenergic receptor
partial agonist
Humans
UBeta-2 adrenergic receptor
partial agonist
Humans
Absorption

Well absorbed from the Gl tract with an absolute bioavailability of approximately 40% for the parent compound.

Volume of distribution

Not Available

Protein binding

26%

Metabolism

Subject to extensive first-pass hepatic biotransformation (primarily to diacetolol).

Route of elimination

Elimination via renal excretion is approximately 30% to 40% and by non-renal mechanisms 50% to 60%, which includes excretion into the bile and direct passage through the intestinal wall.

Half-life

The plasma elimination half-life is approximately 3 to 4 hours. The half-life of its metabolite, diacetolol, is 8 to 13 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include extreme bradycardia, advanced atrioventricular block, intraventricular conduction defects, hypotension, severe congestive heart failure, seizures, and in susceptible patients, bronchospasm, and hypoglycemia.

Pathways
PathwayCategory
Acebutolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Acebutolol is combined with Abaloparatide.
AbataceptThe metabolism of Acebutolol can be increased when combined with Abatacept.
AbirateroneThe metabolism of Acebutolol can be decreased when combined with Abiraterone.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Acebutolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Acebutolol.
Food Interactions
  • Take with or without food. Food decreases absorption rate and maximum concentration, but not to a clinically significant extent.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Acebutolol hydrochlorideB025Y34C5434381-68-5KTUFKADDDORSSI-UHFFFAOYSA-N
International/Other Brands
Prent (Bayer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AcebutololTablet200 mgOralSanis Health Inc2010-02-252018-07-16Canada flag
AcebutololTablet400 mgOralSanis Health Inc2010-02-252018-07-16Canada flag
AcebutololTablet100 mgOralSanis Health Inc2010-02-252018-07-16Canada flag
Acebutolol - 400Tablet400 mgOralPro Doc Limitee1996-12-312022-07-14Canada flag
Acebutolol-100Tablet100 mgOralPro Doc Limitee1996-12-312022-07-14Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Acebutolol HydrochlorideCapsule400 mg/1OralANI Pharmaceuticals, Inc.2022-07-25Not applicableUS flag
Acebutolol HydrochlorideCapsule200 mg/1OralAvKARE, Inc.2009-12-142020-02-03US flag
Acebutolol HydrochlorideCapsule400 mg/1OralMylan Pharmaceuticals Inc.1995-04-24Not applicableUS flag
Acebutolol HydrochlorideCapsule200 mg/1OralAmneal Pharmaceuticals LLC2009-12-01Not applicableUS flag
Acebutolol HydrochlorideCapsule400 mg/1OralAvPAK2009-12-012010-09-03US flag

Categories

ATC Codes
C07AB04 — AcebutololC07BB04 — Acebutolol and thiazides
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Acetophenones / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Aryl alkyl ketones / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds / Dialkylamines
show 4 more
Substituents
1,2-aminoalcohol / Acetophenone / Alcohol / Alkyl aryl ether / Alkyl-phenylketone / Amine / Aromatic homomonocyclic compound / Aryl alkyl ketone / Benzenoid / Benzoyl
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide, secondary amino compound, ether, aromatic amide, ethanolamines, propanolamine (CHEBI:2379)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
67P356D8GH
CAS number
37517-30-9
InChI Key
GOEMGAFJFRBGGG-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide
SMILES
CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(=C1)C(C)=O

References

Synthesis Reference
US3857952
General References
Not Available
Human Metabolome Database
HMDB0015324
KEGG Drug
D02338
KEGG Compound
C06803
PubChem Compound
1978
PubChem Substance
46509113
ChemSpider
1901
BindingDB
25755
RxNav
149
ChEBI
2379
ChEMBL
CHEMBL642
Therapeutic Targets Database
DAP000484
PharmGKB
PA448011
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Acebutolol

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Alphapharm Party Ltd.
  • Amneal Pharmaceuticals
  • Bryant Ranch Prepack
  • Caremark LLC
  • Kaiser Foundation Hospital
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Patheon Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Professional Co.
  • Promius Pharma
Dosage Forms
FormRouteStrength
CapsuleOral200 mg/1
CapsuleOral400 mg/1
Tablet, film coatedOral200 MG
Tablet, film coatedOral400 MG
Tablet, film coatedOral100 mg
TabletOral400 mg
TabletOral200 mg / tab
TabletOral
Tablet, coated
TabletOral100 mg
TabletOral200 mg
Injection, solutionIntravenous25 MG/5ML
Prices
Unit descriptionCostUnit
Acebutolol hcl powder7.08USD g
Sectral 400 mg capsule4.48USD capsule
Sectral 200 mg capsule3.37USD capsule
Acebutolol HCl 400 mg capsule1.39USD capsule
Acebutolol 400 mg capsule1.34USD capsule
Sectral 400 mg Tablet1.11USD tablet
Acebutolol HCl 200 mg capsule1.05USD capsule
Acebutolol 200 mg capsule1.01USD capsule
Sectral 200 mg Tablet0.56USD tablet
Acebutolol 400 mg Tablet0.51USD tablet
Apo-Acebutolol 400 mg Tablet0.51USD tablet
Mylan-Acebutolol (Type S) 400 mg Tablet0.51USD tablet
Mylan-Acebutolol 400 mg Tablet0.51USD tablet
Novo-Acebutolol 400 mg Tablet0.51USD tablet
Nu-Acebutolol 400 mg Tablet0.51USD tablet
Rhotral 400 mg Tablet0.51USD tablet
Sectral 100 mg Tablet0.37USD tablet
Acebutolol 200 mg Tablet0.26USD tablet
Apo-Acebutolol 200 mg Tablet0.26USD tablet
Mylan-Acebutolol (Type S) 200 mg Tablet0.26USD tablet
Mylan-Acebutolol 200 mg Tablet0.26USD tablet
Novo-Acebutolol 200 mg Tablet0.26USD tablet
Nu-Acebutolol 200 mg Tablet0.26USD tablet
Rhotral 200 mg Tablet0.26USD tablet
Acebutolol 100 mg Tablet0.17USD tablet
Apo-Acebutolol 100 mg Tablet0.17USD tablet
Mylan-Acebutolol (Type S) 100 mg Tablet0.17USD tablet
Mylan-Acebutolol 100 mg Tablet0.17USD tablet
Novo-Acebutolol 100 mg Tablet0.17USD tablet
Nu-Acebutolol 100 mg Tablet0.17USD tablet
Rhotral 100 mg Tablet0.17USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)136-138Merck Index 13
water solubility259 mg/LNot Available
logP1.71HANSCH,C ET AL. (1995)
Caco2 permeability-5.83ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.172 mg/mLALOGPS
logP1.43ALOGPS
logP1.53Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.91Chemaxon
pKa (Strongest Basic)9.65Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area87.66 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity94.87 m3·mol-1Chemaxon
Polarizability38.51 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7378
P-glycoprotein inhibitor INon-inhibitor0.8557
P-glycoprotein inhibitor IINon-inhibitor0.8664
Renal organic cation transporterNon-inhibitor0.9466
CYP450 2C9 substrateNon-substrate0.8102
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5752
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8721
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9639
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.849
BiodegradationNot ready biodegradable0.8538
Rat acute toxicity2.0487 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9821
hERG inhibition (predictor II)Non-inhibitor0.8555
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00di-9252000000-7827544ebe33c12ef3bb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0297000000-e6ba679e08f8c83ed05d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014r-0194000000-b4896af0f76ecc1c16b2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xs-9331000000-44904acbeb122aaf8bda
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1790000000-d21726882257bba6e42a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kfx-9520000000-5cb2433f611a70e87847
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-1920000000-a65d03ca9dce76359445
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.0868913
predicted
DarkChem Lite v0.1.0
[M-H]-184.57991
predicted
DeepCCS 1.0 (2019)
[M+H]+205.2685913
predicted
DarkChem Lite v0.1.0
[M+H]+186.93793
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.2648913
predicted
DarkChem Lite v0.1.0
[M+Na]+193.11015
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. van den Meiracker AH, Man in 't Veld AJ, Fischberg DJ, Molinoff PB, van Eck HJ, Boomsma F, Derkx FH, Schalekamp MA: Acute and long-term effects of acebutolol on systemic and renal hemodynamics, body fluid volumes, catecholamines, active renin, aldosterone, and lymphocyte beta-adrenoceptor density. J Cardiovasc Pharmacol. 1988 Apr;11(4):413-23. [Article]
  2. Abrahamsson T: Characterization of the beta 1-adrenoceptor stimulatory effects of the partial beta 1-agonists acebutolol, xamoterol, H142/08 and H201/70. Eur J Pharmacol. 1989 May 2;164(1):121-8. [Article]
  3. Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [Article]
  2. Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [Article]
  3. Lima JJ: Relationship between beta adrenoceptor occupancy and receptor down-regulation induced by beta antagonists with intrinsic sympathomimetic activity. J Recept Signal Transduct Res. 1996 Sep-Nov;16(5-6):357-72. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [Article]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
  3. Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [Article]
  2. Terao T, Hisanaga E, Sai Y, Tamai I, Tsuji A: Active secretion of drugs from the small intestinal epithelium in rats by P-glycoprotein functioning as an absorption barrier. J Pharm Pharmacol. 1996 Oct;48(10):1083-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48