{2-hydroxy-3-[2-(prop-2-en-1-yl)phenoxy]propyl}(propan-2-yl)amine

• ChemBase ID: 744
• Molecular Formular: C15H23NO2
• Molecular Mass: 249.34862
• Monoisotopic Mass: 249.17287898
• SMILES: O(CC(O)CNC(C)C)c1c(CC=C)cccc1
• Canonical SMILES: C=CCc1ccccc1OCC(CNC(C)C)O
• InChI: InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3
• InChIKey: PAZJSJFMUHDSTF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-hydroxy-3-[2-(prop-2-en-1-yl)phenoxy]propyl}(propan-2-yl)amine
• IUPAC Traditional name: alprenolol
• Brand Name: Apllobal; Aptine; Aptol Duriles; Gubernal; Regletin; Yobir
• Synonyms: Alprenololum [INN-Latin]; Alfeprol [Russian]; Alpheprol; Alprenolol

Database IDs

• CAS Number: 13655-52-2
• PubChem SID: 46506033; 160964207
• PubChem CID: 2119
• CHEBI ID: 51211
• ATC CODE: C07AA01
• CHEMBL: 266195
• Chemspider ID: 2035
• DrugBank ID: DB00866
• IUPHAR ligand ID: 563
• KEGG ID: D07156
• Unique Ingredient Identifier: 877K5MQ27W
• Wikipedia Title: Alprenolol

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.50044185
• LogD (pH = 7.4): 0.4675513
• Log P: 2.6927898
• Molar Refractivity: 74.6628 cm^3
• Polarizability: 29.495447 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true
• Acid pKa: 14.087952

ALOGPS 2.1

• Log P: 2.59
• LOG S: -3.12
• Solubility (Water): 1.88e-01 g/l

PROPERTIES

Physical Property

• Solubility: 547 mg/L
• Hydrophobicity(logP): 2.8

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 2-3 hours → 4-OH-alprenolol
• Protein Bound: 80% - 90%

DETAILS

DrugBank - DB00866

• Drug Groups: approved
• Description: One of the adrenergic beta-antagonists used as an antihypertensive, anti-anginal, and anti-arrhythmic agent. [PubChem]
• Indication: For the treatment of hypertension, angina, and arrhythmia
• Pharmacology: Alprenolol is a non-selective beta-blocker used in the treatment of hypertension, edema, ventricular tachycardias, and atrial fibrillation. Alprenolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Alprenolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Alprenolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, alprenolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
• Toxicity: LD₅₀=597.0 mg/kg (Orally in rats)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. One of the active metabolites, 4-OH-alprenolol, is an active beta-blocker.
• Half Life: 2-3 hours
• Protein Binding: 80-90%