Title: Vinblastine
CAS Registry Number: 865-21-4
CAS Name: Vincaleukoblastine
Synonyms: VLB
Molecular Formula: C46H58N4O9
Molecular Weight: 810.97
Percent Composition: C 68.13%, H 7.21%, N 6.91%, O 17.76%
Literature References: Antitumor alkaloid isolated from periwinkle,
Vinca rosea Linn.,
Apocynaceae; inhibits microtubule assembly. Identification: R. L. Noble
et al., Ann. N.Y. Acad. Sci. 76, 882-894 (1958). Isolation and characterization: M. Gorman
et al., J. Am. Chem. Soc. 81, 4745, 4754 (1959); C. T. Beer
et al., US 3097137 (1963 to CPD Ltd.). Structure: N. Neuss
et al., J. Am. Chem. Soc. 86, 1440 (1964). 13C-NMR spectral analysis: E. Wenkert
et al., Helv. Chim. Acta 58, 1560 (1975). Synthesis from catharanthine and vindoline,
q.q.v.: P. Mangeney
et al., J. Am. Chem. Soc. 101, 2243 (1979); J. P. Kutney
et al., Heterocycles 27, 1845 (1988). Enantioselective synthesis: M. E. Kuehne
et al., J. Org. Chem. 56, 513 (1991). Toxicology: C. Lu, M. Meistrich,
Cancer Res. 39, 3575 (1979). Clinical trial in combination with bleomycin, methotrexate,
q.q.v. in Hodgkin's disease: P. G. Gobbi
et al., J. Clin. Oncol. 14, 527 (1996). Review of pharmacology, toxicology and pharmacokinetics: W. P. Brade,
Beitr. Onkol. 6, 95-123 (1981). Comprehensive description: F. J. Muhtadi, A. F. A. Afify,
Anal. Profiles Drug Subs. Excip. 21, 611-658 (1992).
Properties: Solvated needles from methanol, mp 211-216°. [a]D23 -32° (c = 0.88 in methanol). uv max (ethanol): 214, 259 nm (log e 4.74, 4.22). pKa1 5.4; pKa2 7.4. Practically insol in water, petr ether. Sol in alcohols, acetone, ethyl acetate, CHCl3.
Melting point: mp 211-216°
pKa: pKa1 5.4; pKa2 7.4
Optical Rotation: [a]D23 -32° (c = 0.88 in methanol)
Absorption maximum: uv max (ethanol): 214, 259 nm (log e 4.74, 4.22)
Derivative Type: Sulfate
CAS Registry Number: 143-67-9
Manufacturers' Codes: 29060-LE
Trademarks: Exal (Nippon Kayaku); Velban (Lilly); Velbe (Lilly)
Molecular Formula: C46H58N4O9.H2SO4
Molecular Weight: 909.05
Percent Composition: C 60.78%, H 6.65%, N 6.16%, O 22.88%, S 3.53%
Properties: Crystallizes as hydrate, mp 284-285°. [a]D26 -28° (c = 1.01 in methanol). uv max (methanol): 212, 262, 284, 292 nm (log e 4.75, 4.28, 4.22, 4.18). Very slightly sol in ethanol. Practically insol in ether. One part is sol in 10 parts of water, 50 parts of chloroform. LD50 i.v. in mice: 9.5 mg/kg (Lu, Meistrich).
Melting point: mp 284-285°
Optical Rotation: [a]D26 -28° (c = 1.01 in methanol)
Absorption maximum: uv max (methanol): 212, 262, 284, 292 nm (log e 4.75, 4.28, 4.22, 4.18)
Toxicity data: LD50 i.v. in mice: 9.5 mg/kg (Lu, Meistrich)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products; Vinca Alkaloids.
