Stilbamidine
Title: Stilbamidine
CAS Registry Number: 122-06-5
CAS Name: 4,4¢-(1,2-Ethenediyl)bisbenzenecarboximidamide
Additional Names: 4,4¢-stilbenedicarboxamidine; 4,4¢-diamidinostilbene
Molecular Formula: C16H16N4
Molecular Weight: 264.33
Percent Composition: C 72.70%, H 6.10%, N 21.20%
Literature References: Prepn: A. J. Ewins, J. N. Ashley, GB 510097 (1939 to May & Baker); J. N. Ashley et al., J. Chem. Soc. 1942, 103; of isethionate: G. Newbery, A. P. T. Easson, US 2394003 (1946 to May & Baker). Trypanocidal activity: E. M. Lourie, W. Yorke, Ann. Trop. Med. Parasitol. 33, 289 (1939). Preliminary pharmacology: R. Wien, ibid. 37, 1 (1943). Mechanism of action studies: M. J. Pine, Biochem. Pharmacol. 17, 75 (1968); G. Weissmann et al., ibid. 19, 1251 (1970). Crystal structure: C. Courseille et al., C.R. Seances Acad. Sci. Ser. C 272, 1115 (1971). DNA binding study: N. Gresh, B. Pullman, Mol. Pharmacol. 25, 452 (1984). Early review of pharmacology, mode of action and clinical applications: E. B. Schoenbach, E. M. Greenspan, Medicine 27, 327-377 (1948).
 
Derivative Type: Dihydrochloride
Molecular Formula: C16H18Cl2N4
Molecular Weight: 337.25
Percent Composition: C 56.98%, H 5.38%, Cl 21.02%, N 16.61%
Properties: Needles from water. LD50 in mice (mg/g): 0.031 i.v.; 0.18 s.c. (Wien).
Toxicity data: LD50 in mice (mg/g): 0.031 i.v.; 0.18 s.c. (Wien)
 
Derivative Type: Isethionate
CAS Registry Number: 140-59-0
Manufacturers' Codes: M & B 744
Molecular Formula: C20H28N4O8S2
Molecular Weight: 516.59
Percent Composition: C 46.50%, H 5.46%, N 10.85%, O 24.78%, S 12.41%
Properties: Crystals, discolored by light, dec 290°. uv max: 330 nm (E1%1cm 750). Soly in water: approx 1 g in 2.5 to 3.0 ml H2O; in methanol: 1.5 g/l00 ml. pH of 0.5% aq soln 5.5-6.5.
Absorption maximum: uv max: 330 nm (E1%1cm 750)
 
Therap-Cat: Antiprotozoal (Leishmania, Trypanosoma).
Keywords: Antiprotozoal (Leishmania); Antiprotozoal (Trypanosoma).

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