tert-butyl[(2S)-3-(2-cyclopentylphenoxy)-2-hydroxypropyl]amine

• ChemBase ID: 1186
• Molecular Formular: C18H29NO2
• Molecular Mass: 291.42836
• Monoisotopic Mass: 291.21982917
• SMILES: O(c1c(C2CCCC2)cccc1)C[C@@H](O)CNC(C)(C)C
• Canonical SMILES: O[C@H](COc1ccccc1C1CCCC1)CNC(C)(C)C
• InChI: InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1
• InChIKey: KQXKVJAGOJTNJS-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl[(2S)-3-(2-cyclopentylphenoxy)-2-hydroxypropyl]amine
• IUPAC Traditional name: penbutolol
• Brand Name: Betapressin; Levatol; Levatolol; Lobeta; Paginol
• Synonyms: Penbutolol sulfate; Penbutolol

Database IDs

• CAS Number: 36507-48-9
• PubChem SID: 160964648; 46504929
• PubChem CID: 37464

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.087582
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.34295705
• LogD (pH = 7.4): 1.2368405
• Log P: 3.5452163
• Molar Refractivity: 86.6043 cm^3
• Polarizability: 34.45551 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.84
• LOG S: -4.14
• Solubility (Water): 2.12e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.15 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB01359

• Drug Groups: approved
• Description: Penbutolol is a medication in the class of beta blockers, used in the treatment of high blood pressure. [Wikipedia]
• Indication: Used in the treatment of high blood pressure.
• Pharmacology: Penbutolol is a non-selective beta blocker. Beta-blockers work by affecting the response to some nerve impulses in certain parts of the body. As a result, they decrease the heart's need for blood and oxygen by reducing its workload. They also help the heart to beat more regularly.
• Toxicity: Symptoms of overdose include drowsiness, vertigo, headache, and atriventricular block.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized in the liver by hydroxylation and glucuroconjugation forming a glucuronide metabolite and a semi-active 4-hydroxy metabolite.
• Absorption: Oral bioavailability is 90%.
• Half Life: Phase 1: 2.5 hours; phase 2: 24 hours
• Protein Binding: 80-98% bound to plasma proteins.
• Elimination: The metabolites are excreted principally in the urine.
• External Links: Wikipedia; Drugs.com