Pifarnine
Title: Pifarnine
CAS Registry Number: 56208-01-6
CAS Name: 1-(1,3-Benzodioxol-5-ylmethyl)-4-(3,7,11-trimethyl-2,6,10-dodecatrienyl)piperazine
Additional Names: 1-piperonyl-4-(3,7,11-trimethyl-2,6,10-dodecatrienyl)piperazine
Manufacturers' Codes: U-27
Trademarks: Pifazin (Pierrel)
Molecular Formula: C27H40N2O2
Molecular Weight: 424.62
Percent Composition: C 76.37%, H 9.49%, N 6.60%, O 7.54%
Literature References: Non-anticholinergic gastric anti-secretory agent. Prepn: S. Tricerri et al., DE 2310044 corresp to US 3875163 (1973, 1975 both to Pierrel); eidem, Eur. J. Med. Chem. 9, 555 (1974). Pifarnine is a mixture of four stereoisomers: ZZ, EZ, ZE, EE. Separation does not give compounds with significantly different activity/toxicity ratios from the mixture. Stereochemistry and pharmacology of the four isomers: G. Guadagnini et al., ibid. 10, 585 (1975). Pharmacological study of pifarnine: A. Bianchetti et al., Arzneim.-Forsch. 25, 580 (1975). Physical-chemical and analytical studies: G. Guadagnini et al., Pharm. Ind. 38, 296 (1976). Absorption, distribution, excretion: M. Riva et al., Farmaco Ed. Prat. 34, 542 (1979). Clinical studies: A. Porro et al., ibid. 85; M. Petrillo et al., Curr. Ther. Res. 25, 457 (1979).
Properties: Light yellow viscous liq with a slight odor and bitter taste. uv max (ethanol): 287 nm (E1%1cm 94.6). nD20 1.5235. Relative density at 20°: 1.013-1.015. pK1 4.10; pK2 3.25. Readily sol in most org solvents. Slightly sol in aq solns of organic acids. Practically insol in alkali, water. LD50 in mice, rats (mg/kg): 2175, 2610 orally; 40.6, 33.3 i.v. (Bianchetti). Approx LD50 i.p. in mice: 500 mg/kg (Tricerri, 1974).
pKa: pK1 4.10; pK2 3.25
Index of refraction: nD20 1.5235
Absorption maximum: uv max (ethanol): 287 nm (E1%1cm 94.6)
Density: Relative density at 20°: 1.013-1.015
Toxicity data: LD50 in mice, rats (mg/kg): 2175, 2610 orally; 40.6, 33.3 i.v. (Bianchetti); Approx LD50 i.p. in mice: 500 mg/kg (Tricerri, 1974)
Therap-Cat: Antiulcerative.
Keywords: Antiulcerative.

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