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Bepridil

Bepridil structure

CAS No:
64706-54-3
Formula:
C24H34N2O
Chemical Name:
Bepridil
Synonyms:
1-Pyrrolidineethanamine,β-[(2-methylpropoxy)methyl]-N-phenyl-N-(phenylmethyl)-;β-[(2-Methylpropoxy)methyl]-N-phenyl-N-(phenylmethyl)-1-pyrrolidineethanamine;Bepridil;Org 5730;(±)-Bepridil;dl-Bepridil;99239-95-9;89035-90-5
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

ChEBI: A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.

Solid

Bepridil is a tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl. It has a role as a vasodilator agent, an anti-arrhythmia drug, an antihypertensive agent and a calcium channel blocker. It is a tertiary amine and a member of pyrrolidines.|A long-acting, non selective, calcium channel blocker with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist. It is no longer marketed in the United States, as it has been implicated in causing ventricular arrhythmias (ie. Torsade de pointes).|A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.

Bepridil Basic Attributes

Molecular Weight：

366.54

Exact Mass：

366.54

DSSTox ID：

DTXSID3022663

ATC Code：

C - Cardiovascular system

HScode：

2933990090

Characteristics

PSA：

15.7

XLogP3：

5.2

Appearance：

Solid

Density：

1.054 g/cm3

Melting Point：

128

Boiling Point：

184 °C @ Press: 0.1 Torr

Flash Point：

133.2ºC

Refractive Index：

nD20 1.5538

Water Solubility：

H2O: Slightly soluble

Toxicity

Toxicity Summary：

There has been one experience with overdosage in which a patient inadvertently took a single dose of 1600 mg of bepridil. The patient was observed for 72 hours in intensive care, but no significant adverse experiences were noted.

Protein Binding：

99%

Drug Information

Drug Indication：

For the treatment of hypertension, and chronic stable angina (classic effort-associated angina).

Pharmacology：

Bepridil is a calcium channel blocker that has well characterized anti-anginal properties and known but poorly characterized type 1 anti-arrhythmic and anti-hypertensive properties. It is not related chemically to other calcium channel blockers such as diltiazem hydrochloride, nifedipine and verapamil hydrochloride.

MeSH：

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)|Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)|A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

Absorption：

Rapidly and completely absorbed after oral administration.

Metabolism/Metabolites：

Hepatic.

Biological Half-Life：

24-50 hours

Mechanism of Action：

Bepridil has inhibitory effects on both the slow calcium (L-type) and fast sodium inward currents in myocardial and vascular smooth muscle, interferes with calcium binding to calmodulin, and blocks both voltage and receptor operated calcium channels. Bepridil inhibits the transmembrane influx of calcium ions into cardiac and vascular smooth muscle. This has been demonstrated in isolated myocardial and vascular smooth muscle preparations in which both the slope of the calcium dose response curve and the maximum calcium-induced inotropic response were significantly reduced by bepridil. In cardiac myocytes in vitro, bepridil was shown to be tightly bound to actin. Bepridil regularly reduces heart rate and arterial pressure at rest and at a given level of exercise by dilating peripheral arterioles and reducing total peripheral resistance (afterload) against which the heart works.

MeSH Entry Terms：

1978 CERM

Bepridil Use and Manufacturing

Uses

The new calcium antagonists, in order to inhibit the slow channel of calcium ions, selectively expand the coronary arteries, in addition, can inhibit the sodium and potassium ion channels, and thus have the characteristics of class I a, III and IV antiarrhythmic drugs. The half-life is up to 42h. It can be administered once a day. It is well tolerated and has less toxic and side effects. Mainly used for the prevention and treatment of angina pectoris, and can be used for arrhythmia, hypertension and coronary heart disease.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:366.5
XLogP3:5.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:10
Exact Mass:366.267113712
Monoisotopic Mass:366.267113712
Topological Polar Surface Area:15.7
Heavy Atom Count:27
Complexity:382
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Epichlorohydrin

2-Methoxyethanol

Sodium carbonate

Zinc chloride

Thionyl chloride

Sodium amide

Isobutanol