9986. Vincristine
Nomenclature
Description and 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). LC-MS determn in plasma: M. S. Schmidt et al., J. Pharm. Biomed. Anal. 41, 540 (2006). 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). Review of clinical experience: C. E. M. Gidding et al., Crit. Rev. Oncol. Hematol. 29, 267-287 (1999).
Properties
Blades from methanol, mp 218-220°. [α]D25 +17°; [α]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).Derivative
Sulfate.Nomenclature
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. [α]D26 +8.5° (c = 0.8). uv max (methanol): 218, 252, 285, 293 nm (log ε 4.72, 4.24, 4.18, 4.23).Therapeutic Category
Antineoplastic.
Therapeutic Category (Veterinary)
Antineoplastic.Keywords
Antineoplastic; Alkaloids/Natural Products; Vinca Alkaloids