U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H34N2O
Molecular Weight 366.5396
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPRIDIL, (S)-

SMILES

CC(C)COC[C@H](CN(CC1=CC=CC=C1)C2=CC=CC=C2)N3CCCC3

InChI

InChIKey=UIEATEWHFDRYRU-DEOSSOPVSA-N
InChI=1S/C24H34N2O/c1-21(2)19-27-20-24(25-15-9-10-16-25)18-26(23-13-7-4-8-14-23)17-22-11-5-3-6-12-22/h3-8,11-14,21,24H,9-10,15-20H2,1-2H3/t24-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.google.com/patents/WO2016098128A1 | http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2337 | https://www.ncbi.nlm.nih.gov/pubmed/3259292

Bepridil (trade name Vascor) is an amine calcium channel blocker used to treat angina. 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. 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. Bepridil is no longer sold in the United States, but it is still marketed in other countries. Bepridil has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist. Although, it contains one chiral center, it is generally administered as a racemates. The drug bepridil is a racemic mixture of two enantiomers for the 2R as CID 16048570 and 2S as CID 445143. (R)-isomer of bepridil is more active than (-S)- isomer, in certain cases. In the retrogradely perfused, paced rat heart the higher activity was found for the (+)-enantiomer, which was 4.27 times more potent in increasing coronary flow than the (-)-isomer. The two enantiomers of bepridil showed a lower activity on maximum systolic left ventricular pressure (MSLVP) than on coronary flow, and a similar 3-4 fold stereoselectivity with both parameters.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BEPRICOR

Approved Use

Bepridil is used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina.
Primary
BEPRICOR

Approved Use

Bepridil is used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina.
Primary
BEPRICOR

Approved Use

Bepridil is used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina.
PubMed

PubMed

TitleDatePubMed
Stereoisomers of calcium antagonists discriminate between coronary vascular and myocardial sites.
1988 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Angina Pectoris Prophylaxis: Initial dose: 200 mg orally once a day. Maintenance dose: 300-400 mg orally once a day.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Stock solutions of bepridil enantiomers were prepared at I mmol/1 in absolute ethanol. Final ethanol concentrations never exceeded 0.3%,
The velocities of onset and offset of coronary vasodilatation between the (+)- and the (-)-enantiomers of Bepridil, measured at equipotent concentrations (1-3 umol/1 (-)- and 0.3-1 umol/1 (+)-bepridil (82 +/- 4% of maximum vasodilatation), showed no significant differences. Bepridil displayed a considerable slower onset of negative inotropic activity for both isomers (half time values 17.0 and 15.8 for the (+)- and (-)-enantiomer, respectively). The (+)-bepridil concentration (3 umol/1) was chosen somewhat lower (35% of the contraction left), since at higher MSLVP depression, the negative inotropic activity could not be overcome.
Name Type Language
BEPRIDIL, (S)-
Common Name English
(S)-(-)-BEPRIDIL
Common Name English
1-PYRROLIDINEETHANAMINE, .BETA.-((2-METHYLPROPOXY)METHYL)-N-PHENYL-N-(PHENYLMETHYL)-, (.BETA.S)-
Systematic Name English
(-)-BEPRIDIL
Common Name English
Code System Code Type Description
CAS
110143-75-4
Created by admin on Sat Dec 16 10:54:58 GMT 2023 , Edited by admin on Sat Dec 16 10:54:58 GMT 2023
PRIMARY
PUBCHEM
445143
Created by admin on Sat Dec 16 10:54:58 GMT 2023 , Edited by admin on Sat Dec 16 10:54:58 GMT 2023
PRIMARY
FDA UNII
U73HJZ98FZ
Created by admin on Sat Dec 16 10:54:58 GMT 2023 , Edited by admin on Sat Dec 16 10:54:58 GMT 2023
PRIMARY