Basic information
- CAS
62658-63-3- Standard SMILES
Cc1cc2c(OCC(CNC(C)(C)C)OC(=O)c3ccccc3)cccc2[nH]1- InChIKey
UUOJIACWOAYWEZ-UHFFFAOYSA-N- Molecular formula
- C23H28N2O3
- Average molar mass
- 380.5 g/mol
- Monoisotopic mass
- 380.20999276
Overview
1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate is a methylindole that is 2-methyl-1H-indol-4-ol in which the hydrogen of the hydroxy group is replaced by a 2-(benzoyloxy)-3-(tert-butylamino)propyl group. It is an aromatic ether, a benzoate ester, a methylindole and a secondary amino compound.
Names & identifiers
- Preferred name
- Bopindolol
- IUPAC
- [1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl] benzoate
- English name
- Bopindolol
- Molecular formula
- C23H28N2O3
- Molecular weight
- 380.48
Names & synonyms
BOPINDOLOL62658-63-3(+-)-BopindololBopindololumDTXSID6022684KT304VZO57DTXCID4026842-Propanol, 1-((1,1-dimethylethyl)amino)-3-((2-methyl-1H-indol-4-yl)oxy)-, benzoate (ester), (+-)-RefChem:569816CHEBI:76749C07AA171-(tert-butylamino)-3-((2-methylindo)-4-yl)-2-propanol benzoate
Show more names
Bopindolol USP/EP/BP2-[(1,1-Dimethylethyl)amino]-1-{[(2-methyl-1H-indol-4-yl)oxy]methyl}ethyl benzoate1-[(1,1-DiMethylethyl)aMino]-3-[(2-Methyl-1H-indol-4-yl)oxy]-2-propanol 2-Benzoate2-Propanol, 1-[(1,1-dimethylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-, 2-benzoate2-PROPANOL, 1-[(1,1-DIMETHYLETHYL)AMINO]-3-[(2-METHYL-1H-INDOL-4-YL)OXY]-, BENZOATE (ESTER)(±)-1-[(1,1-DiMethylethyl)aMino]-3-[(2-Methyl-1H-indol-4-yl)oxy]-2-propanol Benzoate (Ester)
rac BopindololBopindolol [INN]1-(tert-Butylamino)-3-((2-methyl-1H-indol-4-yl)oxy)propan-2-yl benzoate[1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl] benzoate69010-88-41-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoateBopindolol (INN)(+/-)-Bopindolol
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 63.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 499
Experimental & physicochemical properties
Melting Point
152–153 [malonate salt]
152 - 153 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 117 · 117-120°C
- Boiling point
- 557 · 557.0±50.0 °C(Predicted)
- Density
- 1.143 · 1.143±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
- pka
- 17.59 · 17.59±0.30(Predicted)
- form
- Solid
- color
- White to Pale Beige
- FDA UNII
- 304 VZO57 · KT304VZO57
- ATC code
- 7 AA17 · C07AA17
- Toxicity
- 50 i.v · LD50 i.v. in mice: 17 mg/kg (Troxler, Seemann, 1977)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 i.v. in mice: 17 mg/kg (Troxler, Seemann, 1977)
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
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.
Mechanism of Action
Bopindolol (as pindolol) non-selectively blocks beta-1 adrenergic receptors mainly in the heart, inhibiting the effects of epinephrine and norepinephrine resulting in a decrease in heart rate and blood pressure. By binding beta-2 receptors in the juxtaglomerular apparatus, Pindolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production and therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
Cellular LocationsMembrane
Metabolite PathwaysBopindolol Action Pathway
Applications
DescriptionBopindolol is a potent, long-acting, non-selective β-adrenergic blocker related to pindolol and useful in the treatment of hypertension. Unlike many other agents of this type, it appears to have negligible effects on serum lipoproteins.
Related reactions
3 records
Compound notes
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