Bepridil

Title: Bepridil
CAS Registry Number: 64706-54-3
CAS Name: b-[(2-Methylpropoxy)methyl]-N-phenyl-N-(phenylmethyl)-1-pyrrolidineethanamine
Additional Names: 1-[2-(N-benzylanilino)-1-(isobutoxymethyl)ethyl]pyrrolidine; 1-isobutoxy-2-pyrrolidino-3-N-benzylanilinopropane; 3-isobutoxy-2-pyrrolidino-N-phenyl-N-benzylpropylamine
Molecular Formula: C24H34N2O
Molecular Weight: 366.54
Percent Composition: C 78.64%, H 9.35%, N 7.64%, O 4.36%
Literature References: Calcium channel blocker with antianginal and antiarrhythmic properties. Prepn: R. Y. Mauvernay et al., DE 2310918; eidem, US 3962238; reissued with structure correction: N. Busch et al., US RE 30577 (1973, 1976, 1981 all to CERM). See also: R. Y. Mauvernay et al., DE 2802864 (1978 to CERM), C.A. 89, 179852s (1978). Cardiovascular pharmacology in dogs: M.-T. Michelin et al., Therapie 32, 485 (1977). Mechanism of action studies: S. Vogel et al., J. Pharmacol. Exp. Ther. 210, 378 (1979); C. Labrid et al., ibid. 211, 546 (1979). Clinical comparison of hemodynamic and coronary changes: J. P. Merillon et al., Therapie 36, 123 (1981). Clinical evaluation in angina: M. K. Sharma et al., Am. J. Cardiol. 61, 1210 (1988).
Properties: Viscous liquid, bp0.1 184°, bp0.5 192°. nD20 1.5538.
Boiling point: bp0.1 184°; bp0.5 192°
Index of refraction: nD20 1.5538
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 74764-40-2
Manufacturers' Codes: CERM-1978
Trademarks: Cordium (Riom); Vascor (Ortho); Unicordium (Riom)
Molecular Formula: C24H34N2O.HCl.H2O
Molecular Weight: 421.02
Percent Composition: C 68.47%, H 8.86%, N 6.65%, O 7.60%, Cl 8.42%
Properties: Crystals, mp 91 ±2°. LD50 in mice (mg/kg): 1955 orally, 23.5 i.v. (Mauvernay, 1978).
Melting point: mp 91 ±2°
Toxicity data: LD50 in mice (mg/kg): 1955 orally, 23.5 i.v. (Mauvernay, 1978)
Therap-Cat: Antianginal.
Keywords: Antianginal; Calcium Channel Blocker; Arylalkylamines.
Beractant Beraprost Berbamine Berberine Berberis Aristata

Bepridil
Bepridil.svg
Systematic (IUPAC) name
N-benzyl-N-(3-isobutoxy-2-pyrrolidin-1-yl-propyl)aniline
Clinical data
Trade names Vascor
AHFS/Drugs.com monograph
MedlinePlus a699051
Pregnancy cat. C (US)
Legal status  ?
Routes Oral
Pharmacokinetic data
Bioavailability Well absorbed
Protein binding 99%
Metabolism Hepatic, CYP3A4-mediated
Half-life 42 hours
Excretion Renal
Identifiers
CAS number 64706-54-3 YesY
ATC code C08EA02
PubChem CID 2351
IUPHAR ligand 2337
DrugBank DB01244
ChemSpider 2261 YesY
UNII 755BO701MA YesY
ChEBI CHEBI:3061 YesY
ChEMBL CHEMBL1008 YesY
Chemical data
Formula C24H34N2O 
Mol. mass 366.54 g/mol
 YesY (what is this?)  (verify)

Bepridil (trade name Vascor) is a calcium channel blocker once used to treat angina. It is no longer sold in the United States.

It is nonselective.[1]

It has been discussed as a possible option in the treatment of atrial fibrillation.[2]

It has been implicated in causing ventricular arrhythmia (Torsade de pointes).