N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide

• ChemBase ID: 1063
• Molecular Formular: C18H28N2O4
• Molecular Mass: 336.42592
• Monoisotopic Mass: 336.20490739
• SMILES: O(CC(O)CNC(C)C)c1c(cc(NC(=O)CCC)cc1)C(=O)C
• Canonical SMILES: CCCC(=O)Nc1ccc(c(c1)C(=O)C)OCC(CNC(C)C)O
• 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)
• InChIKey: GOEMGAFJFRBGGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide
• IUPAC Traditional name: acebutolol
• Brand Name: Monitan; Neptal; Prent; Sectral
• Synonyms: dl-Acebutolol; Acetobutolol; Acebutololo; Acebutolol HCL; Acebutolol Hydrochloride; Acebutolol; N-[3-Acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide Hydrochloride; DL-1-(2-Acetyl-4-butyramido)-3-(isopropylamino)propan-2-ol Hydrochloride; IL-17803A; Acecor; Acetanol; Neptal; Prent; Sectral; Acebutolol Hydrochloride

Database IDs

• CAS Number: 34381-68-5; 37517-30-9
• PubChem SID: 46509113; 160964526
• PubChem CID: 1978
• CHEBI ID: 2379
• ATC CODE: C07AB04
• CHEMBL: 642
• Chemspider ID: 1901
• DrugBank ID: DB01193
• KEGG ID: D02338
• Unique Ingredient Identifier: 67P356D8GH
• Wikipedia Title: Acebutolol
• Medline Plus: a687003

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.912071
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.6467636
• LogD (pH = 7.4): -0.5997952
• Log P: 1.5346816
• Molar Refractivity: 94.8692 cm^3
• Polarizability: 36.50459 Å^3
• Polar Surface Area: 87.66 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.43
• LOG S: -3.29
• Solubility (Water): 1.72e-01 g/l

PROPERTIES

Physical Property

• Solubility: 259 mg/L; DMSO; Methanol; Water
• Apperance: Off-White Powder
• Melting Point: 121°C (249.8°F); 141-143°C
• Hydrophobicity(logP): 1.7

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: oral, iv
• Bioavailability: 40% (range 35 to 50%)
• Excretion: Renal: 30%; Biliary: 60%
• Half Life: 3-4 hours (parent drug); 8-13 hours (active metabolite)
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: B (US); C (Australia)
• US Licence: Acebutolol

DETAILS

DrugBank - DB01193

• Drug Groups: approved
• 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. [PubChem]
• Indication: For the management of hypertension and ventricular premature beats in adults.
• Pharmacology: 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.
• 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
• Biotransformation: Subject to extensive first-pass hepatic biotransformation (primarily to diacetolol).
• Absorption: Well absorbed from the Gl tract with an absolute bioavailability of approximately 40% for the parent compound. In
• 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.
• Protein Binding: 26%
• 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.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A123800

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

REFERENCES

• Cuthbert, O.A., et al.: Br. J. Pharmacol., 43, 639 (1971)
• Singh, B.N., et al.: Drugs, 29, 531 (1971)
• Foster, R.T., et al.: Anal. Profiles Drug Subs., 19, 1 (1971)