Title: Vindesine
CAS Registry Number: 53643-48-4
CAS Name: 3-(Aminocarbonyl)-O4-deacetyl-3-de(methoxycarbonyl)vincaleukoblastine
Additional Names: desacetylvinblastine amide; VDS
Manufacturers' Codes: Compound 112531; NSC-245467
Molecular Formula: C43H55N5O7
Molecular Weight: 753.93
Percent Composition: C 68.50%, H 7.35%, N 9.29%, O 14.85%
Literature References: Synthetic deriv of the dimeric Catharanthus alkaloid vinblastine, q.v. Prepn: G. J. Cullinan, K. Gerzon, DE 2415980 (1974 to Lilly), C.A. 82, 72191r (1975); see also C. J. Burnett et al., J. Med. Chem. 21, 88 (1978). 13C-NMR spectroscopy: D. E. Dorman, J. W. Paschal, Org. Magn. Reson. 8, 413 (1976). Antitumor activity in rodents: M. J. Sweeney et al., Cancer Res. 38, 2886 (1978). Pharmacokinetics: R. J. Owellen et al., ibid. 37, 2603 (1977). Use in acute lymphocytic leukemia of childhood: W. Krivit et al., Cancer Chemother. Pharmacol. 2, 267 (1979). Brief review of preclinical and early clinical data: R. W. Dyke et al., ibid. 229. Toxicology: G. C. Todd et al., Toxicol. Environ. Health 1, 843 (1976); R. J. Owellen et al., Biochem. Pharmacol. 26, 1213 (1977).
Properties: Crystals from ethanol-methanol, mp 230-232°. [a]D25 +39.4° (c = 1.0 in methanol). uv max (methanol): 214, 266, 288, 296 nm (e 53400, 17450, 13950, 12500). pKa¢ (DMF 66%) 5.39, 7.36; (H2O) 6.04, 7.67.
Melting point: mp 230-232°
pKa: pKa¢ (DMF 66%) 5.39, 7.36; (H2O) 6.04, 7.67
Optical Rotation: [a]D25 +39.4° (c = 1.0 in methanol)
Absorption maximum: uv max (methanol): 214, 266, 288, 296 nm (e 53400, 17450, 13950, 12500)
Derivative Type: Sulfate salt
CAS Registry Number: 59917-39-4
Manufacturers' Codes: LY-099094
Trademarks: Eldisine (Lilly); Fildesin (Shionogi)
Molecular Formula: C43H55N5O7.H2SO4
Molecular Weight: 852.00
Percent Composition: C 60.62%, H 6.74%, N 8.22%, O 20.66%, S 3.76%
Properties: Amorphous solid from ethanol-isopropyl alcohol, mp >250° (solvated form). LD50 in mice, rats (mg/kg): 6.3 ± 0.6, 2.0 ± 0.2 i.v. (Todd); in mice: 8.8 ± 2.5 i.p. (Owellen, Biochem. Pharmacol.).
Melting point: mp >250° (solvated form)
Toxicity data: LD50 in mice, rats (mg/kg): 6.3 ± 0.6, 2.0 ± 0.2 i.v. (Todd); in mice: 8.8 ± 2.5 i.p. (Owellen, Biochem. Pharmacol.)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products; Vinca Alkaloids. |