Vincristine
Title: Vincristine
CAS Registry Number: 57-22-7
CAS Name: 22-Oxovincaleukoblastine
Additional Names: leurocristine; VCR; LCR
Molecular Formula: C46H56N4O10
Molecular Weight: 824.96
Percent Composition: C 66.97%, H 6.84%, N 6.79%, O 19.39%
Literature References: Antitumor alkaloid isolated from Vinca rosea Linn. (Catharanthus roseus G. Don), Apocynaceae: Svoboda, Lloydia 24, 173 (1961). Structure: Neuss et al., J. Am. Chem. Soc. 86, 1440 (1964); Moncrief, Lipscomb, ibid. 87, 4963 (1965). Pharmacology: R. H. Adamson et al., Arch. Int. Pharmacodyn. Ther. 157, 299 (1965); S. M. Sieber et al., Cancer Treat. Rep. 60, 127 (1976). Prepn and pharmacology of [3H]vincristine: Owellen, Donigian, J. Med. Chem. 15, 894 (1972). Symposium on vincristine: Cancer Chemother. Rep. 52, 453-535 (1968). Biosynthesis from catharanthine and vindoline, q.q.v.: A. Rahman et al., Tetrahedron Lett. 1976, 2351; P. Mangeney et al., J. Am. Chem. Soc. 101, 2243 (1979). Comprehensive description of the sulfate: J. H. Burns, Anal. Profiles Drug Subs. 1, 463-480 (1972); F. J. Muhtadi, A. F. A. Afify, Anal. Profiles Drug Subs. Excip. 22, 517-533 (1993).
Properties: Blades from methanol, mp 218-220°. [a]D25 +17°; [a]D25 +26.2° (ethylene chloride). pKa: 5.0, 7.4 in 33% DMF. uv max (ethanol): 220, 255, 296 nm (log am 4.65, 4.21, 4.18). LD50 i.p. in mice: 5.2 mg/kg (Adamson).
Melting point: mp 218-220°
pKa: pKa: 5.0, 7.4 in 33% DMF
Optical Rotation: [a]D25 +17°; [a]D25 +26.2° (ethylene chloride)
Absorption maximum: uv max (ethanol): 220, 255, 296 nm (log am 4.65, 4.21, 4.18)
Toxicity data: LD50 i.p. in mice: 5.2 mg/kg (Adamson)
 
Derivative Type: Sulfate
CAS Registry Number: 2068-78-2
Trademarks: Kyocristine (Kyorin); Oncovin (Lilly); Vincrex (BMS)
Molecular Formula: C46H56N4O10.H2SO4
Molecular Weight: 923.04
Percent Composition: C 59.86%, H 6.33%, N 6.07%, O 24.27%, S 3.47%
Properties: Crystals from ethanol. mp 273-281°. One part sol in 2 parts water, in 30 parts chloroform. Slightly sol in ethanol. Practically insol in ether. [a]D26 +8.5° (c = 0.8). uv max (methanol): 218, 252, 285, 293 nm (log e 4.72, 4.24, 4.18, 4.23).
Melting point: mp 273-281°
Optical Rotation: [a]D26 +8.5° (c = 0.8)
Absorption maximum: uv max (methanol): 218, 252, 285, 293 nm (log e 4.72, 4.24, 4.18, 4.23)
 
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products; Vinca Alkaloids.

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