Identification

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Name
Acebutolol
Accession Number
DB01193  (APRD00772)
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Acebutolol HydrochlorideB025Y34C5434381-68-5KTUFKADDDORSSI-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcebutololTabletOralSanis Health Inc2010-02-252018-07-16Canada
AcebutololTabletOralSanis Health Inc2010-02-252018-07-16Canada
AcebutololTabletOralSanis Health Inc2010-02-252018-07-16Canada
Acebutolol - 400TabletOralPro Doc Limitee1996-12-31Not applicableCanada
Acebutolol-100TabletOralPro Doc Limitee1996-12-31Not applicableCanada
Acebutolol-200TabletOralPro Doc Limitee1996-12-31Not applicableCanada
Monitan 100TabletOralWyeth Ltd.1995-12-312004-09-13Canada
Monitan 200TabletOralWyeth Ltd.1995-12-312007-01-22Canada
Monitan 400TabletOralWyeth Ltd.1994-12-312007-01-22Canada
Monitan Tab 200mgTabletOralWyeth Ltd.1987-12-311996-09-10Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acebutolol HydrochlorideCapsule400 mg/1OralAmneal Pharmaceuticals LLC2009-12-01Not applicableUs
Acebutolol HydrochlorideCapsule400 mg/1OralPhysicians Total Care, Inc.2005-04-22Not applicableUs
Acebutolol HydrochlorideCapsule200 mg/1OralAvPAK2010-09-16Not applicableUs
Acebutolol HydrochlorideCapsule400 mg/1OralMylan Pharmaceuticals Inc.1995-04-24Not applicableUs
Acebutolol HydrochlorideCapsule200 mg/1OralAmneal Pharmaceuticals LLC2009-12-01Not applicableUs
Acebutolol HydrochlorideCapsule200 mg/1OralPhysicians Total Care, Inc.2006-02-012012-06-30Us
Acebutolol HydrochlorideCapsule200 mg/1Oralbryant ranch prepack2009-12-012010-06-01Us
Acebutolol HydrochlorideCapsule200 mg/1OralMylan Pharmaceuticals Inc.1995-04-24Not applicableUs
Acebutolol HydrochlorideCapsule400 mg/1OralAmneal Pharmaceuticals of New York Llc2009-12-01Not applicableUs
Acebutolol HydrochlorideCapsule200 mg/1OralMajor2009-12-012018-09-13Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Prent (Bayer)
Categories
UNII
67P356D8GH
CAS number
37517-30-9
Weight
Average: 336.4259
Monoisotopic: 336.204907394
Chemical Formula
C18H28N2O4
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(C)=O)=C(OCC(O)CNC(C)C)C=C1

Pharmacology

Indication

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

Associated Conditions
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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

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

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
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.

Affected organisms
  • Humans and other mammals
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
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Acebutolol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Acebutolol.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Acebutolol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Acebutolol.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Acebutolol.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Acebutolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Acebutolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
25-desacetylrifapentineThe metabolism of Acebutolol can be increased when combined with 25-desacetylrifapentine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Acebutolol is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe risk or severity of adverse effects can be increased when Acebutolol is combined with 3,5-diiodothyropropionic acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take without regard to meals; absorption rate and maximal concentration are slightly reduced but the extent of absorption is not affected.

References

Synthesis Reference
US3857952
General References
Not Available
External Links
Human Metabolome Database
HMDB0015324
KEGG Drug
D02338
KEGG Compound
C06803
PubChem Compound
1978
PubChem Substance
46509113
ChemSpider
1901
BindingDB
25755
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
ATC Codes
C07AB04 — AcebutololC07BB04 — Acebutolol and thiazides
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases1
3TerminatedTreatmentHemangiomas1
4CompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentArrhythmia / Atrial Fibrillation (AF)1

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
TabletOral
TabletOral100 mg
TabletOral200 mg
TabletOral400 mg
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)9.57ChemAxon
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Alkyl-phenylketone / Acetophenone / Benzoyl / Phenol ether / Aryl alkyl ketone / Phenoxy compound / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / 1,2-aminoalcohol
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide, secondary amino compound, ether, aromatic amide, ethanolamines, propanolamine (CHEBI:2379)

Targets

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. [PubMed:2453744]
  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. [PubMed:2568935]
  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. [PubMed:16268148]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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. [PubMed:16268148]
  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. [PubMed:10433496]
  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. [PubMed:8968966]

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. [PubMed:27836712]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
  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 . [PubMed:17125412]

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. [PubMed:12948019]
  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. [PubMed:8953513]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2019 10:34