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Acebutolol

HCID 1978
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
37517-30-9
Standard SMILES
CCCC(=O)Nc1ccc(OCC(O)CNC(C)C)c(C(C)=O)c1
InChIKey
GOEMGAFJFRBGGG-UHFFFAOYSA-N
Molecular formula
C18H28N2O4
Average molar mass
336.4 g/mol
Monoisotopic mass
336.20490738

Overview

Acebutolol is an ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol. It has a role as a sympathomimetic agent, a beta-adrenergic antagonist, an antihypertensive agent and an anti-arrhythmia drug. It is a member of ethanolamines, an ether, a monocarboxylic acid amide, a propanolamine, a secondary amino compound and an aromatic amide. It is a conjugate base of an acebutolol(1+).

Names & identifiers

Preferred name
Acebutolol
IUPAC
N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide
English name
Acebutolol
Molecular formula
C18H28N2O4
Molecular weight
336.43

Names & synonyms

acebutolol37517-30-9AcetobutololAcebutololoAcebutololum(+-)-Acebutolol5'-Butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenoneCHEBI:2379C07AB0467P356D8GHN-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide
Show more names
N-(3-acetyl-4-(2-hydroxy-3-(isopropylaMino)propoxy)phenyl)butyraMidePrentSectralAcebuprololdl-AcebutololAcebutolo HClAcebutolol Monome
DTXSID2048539N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamideN-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamideN-[3-acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]butanamideButanamide, N-(3-acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)-,monohydrochloride,(+-)-M & B 17803ANovoAcebutololApoAcebutolol

Database identifiers

CAS
37517-30-9

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
87.7 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
10
Heavy atoms
24
Formal charge
0
Complexity
400

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP · 2 items

1.7

1.71

Solubility1.72e-01 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics

Pharmaceuticals

Melting Point · 2 items

136-138

119 - 123 °C

Physical DescriptionSolid
Dissociation Constants · 2 items

9.52

9.67

Collision Cross Section · 2 items

187.43 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

190.2 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

H362 (100%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

P203, P260, P263, P264, P270, and P318 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Other Safety InformationIMAP assessments - Butanamide, N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]-, (.+-.)-: Environment tier I assessment
Hazard Classes and CategoriesLact. (100%)

Toxicology

Hepatotoxicity · 1 item

Acebutolol is associated with a low rate of mild-to-moderate elevations of serum aminotransferase levels during treatment. These enzyme elevations are usually asymptomatic and transient and resolve even with continuation of therapy. There have been few documented cases of clinically apparent, acute liver injury attributed to acebutolol. The time to onset of injury was typically between 1 and 6 weeks of starting. The pattern of liver enzyme elevations was usually hepatocellular with an acute hepatitis-like presentation, although some cases present with a mixed pattern of enzymes. Fever commonly accompanied the liver injury, but usually without rash and eosinophia. Acebutolol is known to induce autoantibodies such as antinuclear antibody in 10% to 30% of patients, some of whom develop a lupus-like syndrome with fatigue, skin rash and arthralgias. Serum enzyme elevations may accompany this syndrome, but jaundice and symptoms of liver injury are uncommon. The published cases of hepatotoxicity due to acebutolol were relatively mild, self-limited and recovery was rapid upon stopping. Rechallenge resulted in rapid recurrence of injury.

Chemistry & industry

Pharmacology

ATC Code · 3 items

C07AB04

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding26%
Pharmacodynamics · 1 item

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 · 1 item

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.

Biological Half-LifeThe plasma elimination half-life is approximately 3 to 4 hours. The half-life of its metabolite, diacetolol, is 8 to 13 hours.
Metabolism/MetabolitesSubject to extensive first-pass hepatic biotransformation (primarily to diacetolol).
FDA Pharmacological Classification · 5 items

67P356D8GH

ACEBUTOLOL

Mechanisms of Action [MoA] - Adrenergic beta-Antagonists

Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker

Acebutolol is a beta-Adrenergic Blocker. The mechanism of action of acebutolol is as an Adrenergic beta-Antagonist.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
1978
DTXSID
DTXSID2048539
ChEMBL
CHEMBL642
ChEBI
CHEBI:2379
UNII
67P356D8GH
EC Number
253-539-0
Nikkaji
J29.383K
Melting point
119 · 119-123°C
Boiling point
472.9 °C · 472.9°C (rough estimate)
Density
1.1748 · 1.1748 (rough estimate)
refractive index
1.57 · 1.5700 (estimate)
storage temp.
-20 °C · -20°C Freezer
solubility
10 mg/mL,DMSO: · DMF: 10 mg/mL,DMSO: 5 mg/mL,Ethanol: 5 mg/mL,PBS (pH 7.2): 0.3 mg/mL
form
A solid
pka
9.4 · pKa 9.40 (Uncertain)
color
Crystals
Water Solubility
259 mg/L · 259 mg/L
CAS DataBase Reference
37517 · 37517-30-9(CAS DataBase Reference)
FDA UNII
67 P356D8GH · 67P356D8GH
ATC code
7 AB04 · C07AB04
NIST Chemistry Reference
Acebutolol(37517-30-9)
EPA Substance Registry System
3 · Butanamide, N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]- (37517-30-9)
Protein binding
26 % · 26%
Excreted unchanged in urine
55 % · 55%
Volume of distribution
1.2 · 1.2(L/kg)
Biological half-life
3 · 3-4 (8-13 for active metabolite) / Increased (32 for active metabolite)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
362 · H362
Precautionary statements
201 · P201-P260-P263-P264-P270-P308+P313
Toxicity
152 mg/kg:CVS,BPR · TDLo orl-wmn: 152 mg/kg:CVS,BPR JTCTDW 20,69,83
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

acebutolol

DILI Positive

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals · 6 items

Acebutolol

4.7

19.7

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.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 200 mg/day, Lowest Therapeutic Dose (LTD): 2.5 mg/kg-day, and Screening Dose: 0.001 mg/kg-day.

27-Dec-20

Safety data

Toxicity
TDLo orl-wmn: 152 mg/kg:CVS,BPR JTCTDW 20,69,83
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H362
Precautionary statements
P201-P260-P263-P264-P270-P308+P313
MeSH Pharmacological Classification · 4 items

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.

Drugs that bind to and block the activation of ADRENERGIC BETA-1 RECEPTORS.

Absorption, Distribution and Excretion · 2 items

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

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.

Cellular LocationsMembrane
Metabolite PathwaysAcebutolol Action Pathway

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationPharmaceuticals
Applications · 4 items

UsesAcebutol is 3′-acetyl-4′-[2-hydroxy-3-(iso-propylamino)propoxy] butyranilide (12.1.6) [9,10].Acebutol is a selective β1-adrenoblocker. It possesses antianginal, antihypotensive, and antiarrhythmic action. It is used for arterial hypertension, preventing attacks of angina, and cardiac rhythm disturbances.

UsesCardioselective adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II)

UsesCardioselective β-adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

General DescriptionAcebutolol is one of the very few β-blockers whosemetabolite plays a significant role in its pharmacological actions.This drug is absorbed well from the gastrointestinaltract, but it undergoes extensive first-pass metabolic conversionto diacetolol by hydrolytic conversion of the amidegroup to the amine, followed by acetylation of the amine. After oral administration, plasma levels of diacetololare higher than those of acebutolol. Diacetolol is also aselective β1-blocker with partial agonistic activity; it has littlemembrane-stabilizing activity. It has a longer half-life (8–12hours) than the parent drug and is excreted by the kidneys.

Upstream & downstream products

Upstream raw materials

D/L-amphetamine hydrochlorideAcetophenoneButyramideIsopropylamineEpichlorohydrinAluminum chlorideSodium ethoxideAcetyl chlorideCyclopropanecarboxylic acid

Suppliers19 total

盐城通铭生物科技有限公司15195160625 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
宝鸡缔都医药化工有限公司029-81145305 17791533577 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
深圳摩科生化科技有限公司18627923403 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
深圳博泰尔生物技术有限公司13316949107 13316968096 · [email protected]
海蔚化学86-21-51086038 · [email protected]
湖北摩科化学有限公司18627753421; 18627756402 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]

Additional notes

DefinitionChEBI: An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.