tert-butyl[3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl]amine

• ChemBase ID: 6408
• Molecular Formular: C14H22ClNO2
• Molecular Mass: 271.78298
• Monoisotopic Mass: 271.13390663
• SMILES: Clc1c(OCC(O)CNC(C)(C)C)cc(cc1)C
• Canonical SMILES: OC(COc1cc(C)ccc1Cl)CNC(C)(C)C
• InChI: InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3
• InChIKey: HQIRNZOQPUAHHV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl[3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl]amine
• IUPAC Traditional name: bupranolol
• Brand Name: Ophtorenin; Adomed; Betadrenol
• Synonyms: Bupranololum; Bupranol; Bupranolol

Database IDs

• CAS Number: 23284-25-5
• PubChem SID: 160969715
• PubChem CID: 2475

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.087501
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.20999743
• LogD (pH = 7.4): 0.6838863
• Log P: 2.992262
• Molar Refractivity: 74.8597 cm^3
• Polarizability: 29.685394 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.14
• LOG S: -3.28
• Solubility (Water): 1.43e-01 g/l

DETAILS

DrugBank - DB08808

• Drug Groups: approved
• Description: Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to "propranolol":http://www.drugbank.ca/drugs/DB00571.
• Indication: Used to manage hypertension and tachycardia. Also used to treat glaucoma.
• Pharmacology: Bupranolol is a competitive, nonselective beta-blocker similar to propanolol without intrinsic sympathomimetic activity.
• Toxicity: Symptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm.
• Affected Organisms: Humans and other mammals
• Biotransformation: Over 90% undergo first-pass metabolism. The main metabolite is carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid, of which 88% are eliminated renally within 24 hours.
• Absorption: Quickly and completely absorbed from the gut with less than 10% oral bioavailability.
• Half Life: 2-4 hours
• Protein Binding: 76%