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

• ChemBase ID: 1360
• Molecular Formular: C15H23NO3
• Molecular Mass: 265.34802
• Monoisotopic Mass: 265.1677936
• SMILES: O(CC(O)CNC(C)C)c1c(OCC=C)cccc1
• Canonical SMILES: C=CCOc1ccccc1OCC(CNC(C)C)O
• InChI: InChI=1S/C15H23NO3/c1-4-9-18-14-7-5-6-8-15(14)19-11-13(17)10-16-12(2)3/h4-8,12-13,16-17H,1,9-11H2,2-3H3
• InChIKey: CEMAWMOMDPGJMB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-hydroxy-3-[2-(prop-2-en-1-yloxy)phenoxy]propyl}(propan-2-yl)amine
• IUPAC Traditional name: oxprenolol
• Brand Name: Coretal; Laracor; Slow-pren; Trasacor; Trasicor
• Synonyms: (+)-1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-ol; (+-)-oxprenolol; (1)-1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-ol; 1-(Isopropylamino)-2-hydroxy-3-(o-(allyloxy)phenoxy)propane; 1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)-2-propanol; 1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)-2-propanol; DL-oxprenolol; Osprenololo [dcit]; Oxprenololum [inn-latin]; Oxprenolol; 1-[(1-Methylethyl)amino]-3-[2-(2-propen-1-yloxy)phenoxy]-2-propanol Hydrochloride; 1-(Isopropylamino)-2-hydroxy-3-[o-(allyloxy)phenoxy]propane Hydrochloride; Coretal; Laracor; Paritane; Trasacor; Oxprenolol Hydrochloride

Database IDs

• CAS Number: 6452-73-9; 6452-71-7
• PubChem SID: 160964820; 46508996
• PubChem CID: 4631
• ATC CODE: C07AA02
• CHEMBL: 546
• Chemspider ID: 4470
• DrugBank ID: DB01580
• KEGG ID: D08318
• Unique Ingredient Identifier: 519MXN9YZR
• Wikipedia Title: Oxprenolol

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.08779
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.0254339
• LogD (pH = 7.4): -0.057440292
• Log P: 2.1677978
• Molar Refractivity: 76.0014 cm^3
• Polarizability: 30.160152 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.44
• LOG S: -2.59
• Solubility (Water): 6.80e-01 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 91-93°C
• Hydrophobicity(logP): 2.10 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

Pharmacology Properties

• Admin Routes: oral
• Bioavailability: 20-70%
• Excretion: Renal ; Lactic (In lactiferous females)
• Half Life: 1-2hours
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: C (Australia)

DETAILS

DrugBank - DB01580

• Drug Groups: approved
• Description: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety. [PubChem]
• Indication: Used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.
• Pharmacology: Oxprenolol is a non-selective beta blocker with some intrinsic sympathomimetic activity. Oxprenolol is a lipophilic beta blocker which passes the blood-brain barrier more easily than water soluble beta blockers. As such, it is associated with a higher incidence of CNS-related side effects than hydrophilic ligands such as atenolol, sotalol and nadolol. Oxprenolol is an potent beta-blocker and should not be administered to asthmatics because it can cause irreversible airway failure and inflammation.
• Toxicity: Symptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Oral bioavailability is 20-70%.
• Half Life: 1-2 hours
• References: McDevitt DG: Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs. Eur Heart J. 1987 Dec;8 Suppl M:9-14. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - O870500

β-Adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.

REFERENCES

• McDevitt DG: Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs. Eur Heart J. 1987 Dec;8 Suppl M:9-14. Pubmed
• Garteiz, et al.: J. Pharmacol. Exp. Ther., 179, 354 (1971)
• Taylor, S.H., et al.: N. Engl. J. Med., 307, 1293 (1971)