1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate

• ChemBase ID: 6407
• Molecular Formular: C23H28N2O3
• Molecular Mass: 380.48002
• Monoisotopic Mass: 380.20999277
• SMILES: O(C(CNC(C)(C)C)COc1c2c([nH]c(c2)C)ccc1)C(=O)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1)OC(COc1cccc2c1cc([nH]2)C)CNC(C)(C)C
• InChI: InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3
• InChIKey: UUOJIACWOAYWEZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate
• IUPAC Traditional name: bopindolol
• Brand Name: Sandonorm
• Synonyms: Bopindolol; 1-[(1,1-Dimethylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol 2-Benzoate; (±)-1-[(1,1-Dimethylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol Benzoate (Ester); (±)-Bopindolol; rac Bopindolol

Database IDs

• CAS Number: 69010-88-4; 62658-63-3
• PubChem SID: 160969714
• PubChem CID: 44112

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.797941
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.534566
• LogD (pH = 7.4): 2.7915826
• Log P: 4.668419
• Molar Refractivity: 111.0719 cm^3
• Polarizability: 44.592506 Å^3
• Polar Surface Area: 63.35 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.45
• LOG S: -5.38
• Solubility (Water): 1.60e-03 g/l

PROPERTIES

Physical Property

• Solubility: 3.3 mg/ml [malonate salt]

DETAILS

DrugBank - DB08807

• Drug Groups: approved
• Description: Bopindolol (INN) is a beta blocker. It is an ester which acts as a prodrug for "pindolol":http://drugbank.ca/drugs/DB00960.
• Indication: For the management of hypertension, edema, ventricular tachycardias, and atrial fibrillation.
• Pharmacology: Bopindolol is a prodrug of pindolol. Pindolol is a non-selective beta-adrenergic antagonist (beta-blocker) which possesses intrinsic sympathomimetic activity (ISA) in therapeutic dosage ranges but does not possess quinidine-like membrane stabilizing activity. Pindolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Pindolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Pindolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, pindolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Toronto Research Chemicals - B675400

Bopindolol is an ester prodrug of Pindolol (P468000). Bopindolol is a long acting β-adrenoceptor blocking agent. Bopindolol displays antispasmogenic activity mediated by α1-adrenoceptors and 5-HT2 receptors.

REFERENCES

• Turner, D.R. et al.: Br. J. Clin. Pharmacol., 17, 295 (1984)
• Brodde, O.E. et al.: J. Cardio. Pharmacol., 8, S70 91986); Doggrell, S.A.: Med, Sci. Res., 17, 681 (1984)