Verapamil
Title: Verapamil
CAS Registry Number: 52-53-9
CAS Name: a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)benzeneacetonitrile
Additional Names: 5-[(3,4-dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile; a-isopropyl-a-[(N-methyl-N-homoveratryl)-g-aminopropyl]-3,4-dimethoxyphenylacetonitrile; iproveratril
Manufacturers' Codes: D-365
Molecular Formula: C27H38N2O4
Molecular Weight: 454.60
Percent Composition: C 71.33%, H 8.43%, N 6.16%, O 14.08%
Literature References: Prototype calcium antagonist; vasodilating activity resides primarily in the (S)-isomer. Both isomers inhibit the p-glycoprotein efflux pump in multidrug resistant tumor cells. Prepn: BE 615861; Dengel, US 3261859 (1962, 1966 both to Knoll). Pharmacology: H. Haas, G. Härtfelder, Arzneim.-Forsch. 12, 549 (1962). Physical and chemical data: W. Appel, ibid. 562. Synthesis and absolute configuration of enantiomers: H. Ramuz, Helv. Chim. Acta 58, 2050 (1975). Stereospecific synthesis: L. J. Theodore, W. L. Nelson, J. Org. Chem. 52, 1309 (1987). HPLC determn of enantiomers and metabolites in plasma: G. Stagni, W. R. Gillespie, J. Chromatogr. B 667, 349 (1995). Comprehensive description: Z. L. Chang, Anal. Profiles Drug Subs. 17, 643-674 (1988). Review of pharmacology and therapeutic use in arrhythmias: B. N. Singh et al., Drugs 25, 125-153 (1983); in hypertension: D. McTavish, E. M. Sorkin, ibid. 38, 19-76 (1989). Clinical trial of dexverapamil as adjunct to cancer chemotherapy: G. Kornek et al., Cancer 76, 1356 (1995); R. J. Motzer et al., J. Clin. Oncol. 13, 1958 (1995).
Properties: Viscous, pale yellow oil, bp0.01 243-246°. nD25 1.5448. Practically insol in water. Sparingly sol in hexane; sol in benzene, ether. Freely sol in the lower alcohols, acetone, ethyl acetate, chloroform.
Boiling point: bp0.01 243-246°
Index of refraction: nD25 1.5448
 
Derivative Type: Hydrochloride
CAS Registry Number: 152-11-4
Trademarks: Berkatens (Berk); Calan (Searle); Cardibeltin (Schwarz); Covera-HS (Searle); Dignover (Sankyo); Falicard (AWD); Flamon (Mepha); Geangin (GEA); Isoptin (Abbott); Quasar (Abbott); Securon (Abbott); Tarka (Abbott); Univer (Zeneus); Veracim (Cimex); Veramex (Sanofi-Synthelabo); Veraptin (Lagap); Verelan (Elan); Vertab (Chiesi); Zolvera (Rosemont)
Molecular Formula: C27H38N2O4.HCl
Molecular Weight: 491.06
Percent Composition: C 66.04%, H 8.01%, N 5.70%, O 13.03%, Cl 7.22%
Properties: Crystals, dec 138.5-140.5° (corr). pH of 0.1% aq soln: 5.25. uv max: 232, 278 nm. Soly (mg/ml): water 83, ethanol (200 proof) 26, propylene glycol 93, ethanol (190 proof) >100, methanol >100, 2-propanol 4.6, ethyl acetate 1.0, DMF >100, methylene chloride >100, hexane 0.001. pKa 8.6. LD50 in mice, rats (mg/kg): 7.6, 16 i.v.; 68, 107 s.c.; 68, 67 i.p.; 163, 114 orally (Haas, Härtfelder).
pKa: pKa 8.6
Absorption maximum: uv max: 232, 278 nm
Toxicity data: LD50 in mice, rats (mg/kg): 7.6, 16 i.v.; 68, 107 s.c.; 68, 67 i.p.; 163, 114 orally (Haas, Härtfelder)
 
Derivative Type: (R)-Form hydrochloride
CAS Registry Number: 38176-02-2; 38321-02-7
Additional Names: Dexverapamil hydrochloride
Properties: Crystals, mp 131-133°. [a]D25 +8.9° (c = 5.01 in ethanol).
Melting point: mp 131-133°
Optical Rotation: [a]D25 +8.9° (c = 5.01 in ethanol)
 
Therap-Cat: Antihypertensive; antianginal; antiarrhythmic (class IV).
Keywords: Antianginal; Antiarrhythmic; Calcium Channel Blocker; Arylalkylamines.

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