 Home > Encyclopedia > Bopindolol

Bopindolol

Bopindolol structure

CAS No:
62658-63-3
Formula:
C23H28N2O3
Chemical Name:
Bopindolol
Synonyms:
2-Propanol,1-[(1,1-dimethylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-,2-benzoate;2-Propanol,1-[(1,1-dimethylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-,benzoate (ester),(±)-;2-Propanol,1-[(1,1-dimethylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-,benzoate (ester);Bopindolol;(±)-Bopindolol;1-(tert-Butylamino)-3-((2-methyl-1H-indol-4-yl)oxy)propan-2-yl benzoate;69010-88-4
Categories:
Organic Chemistry > Amides

Description

Off-White to pale Yellow Solid

Solid

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 a methylindole, a secondary amino compound, an aromatic ether and a benzoate ester.|Bopindolol (INN) is an ester prodrug for the beta blocker [pindolol].

Bopindolol Basic Attributes

Molecular Weight：

380.48

Exact Mass：

380.48

DSSTox ID：

DTXSID6022684

ATC Code：

C - Cardiovascular system

HScode：

2933990090

Characteristics

PSA：

63.4

XLogP3：

4.85970

Appearance：

Solid

Density：

1.143 g/cm3

Melting Point：

152 - 153 °C

Boiling Point：

557ºC at 760 mmHg

Flash Point：

290.7ºC

Refractive Index：

1.592

Water Solubility：

3.3 mg/ml (malonate salt)

Toxicity：

LD50 i.v. in mice: 17 mg/kg (Troxler, Seemann, 1977)

Drug Information

Drug 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.

MeSH：

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. (See all compounds classified as Adrenergic beta-Antagonists.)

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 Entry Terms：

1-(tert-butylamino)-3-((2-methylindo)-4-yl)-2-propanol benzoate

Bopindolol Use and Manufacturing

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.

Computed Properties

Molecular Weight:380.5
XLogP3:4.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:380.20999276
Monoisotopic Mass:380.20999276
Topological Polar Surface Area:63.4
Heavy Atom Count:28
Complexity:499
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes