vincristine michael doe chem 23202 l.
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Vincristine Michael Doe CHEM 23202. Overview. I. Physical Properties II. Synthesis III. Characterization IV. History and Uses V. How it works. General Information 2. CAS Number: 57-22-7 Molecular Formula: C 46 H 56 N 4 O 10 Molecular Weight: 824.97 Melting Point: 218-220 °C

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overview
Overview
  • I. Physical Properties
  • II. Synthesis
  • III. Characterization
  • IV. History and Uses
  • V. How it works
general information 2
General Information2
  • CAS Number: 57-22-7
  • Molecular Formula: C46H56N4O10
  • Molecular Weight: 824.97
  • Melting Point: 218-220°C
  • Clear liquid

(taken by injection)

synthesis from a natural source
Synthesis from a Natural Source
  • Vincristine has two natural sources: Catharanthus roseus (Vinca rosea), the Madagascar periwinkle, and

Tabernaemontana pachysiphon

  • This yield from the Madagascar periwinkle is less than 1μg/g (.0003%)6
synthesis from vinblastine
Synthesis from vinblastine

H2CrO4

Ethyl Acetate

2 hours, -83- -25°C

80-90% yield5

  • This is the easiest and most common method of
  • synthesis, as well as one can give high yields
synthetic production
Synthetic Production
  • Discovered in 2004
  • First route to make synthetic

vincristine6

spectroscopy
Spectroscopy
  • Mass Spectrum4: M+1=825
  • UV Spectrum1: 220, 255, 296 nm
  • IR Spectrum6: 3445, 2924, 2852, 1740, 1681, 1597, 1498, 1458, 1369, 1230, 1033, 747 cm-1
history and uses
History and Uses
  • Discovered in 1953 by Robert L. Noble, and cleared by the FDA in 1963 as Oncovin, marketed by Eli Lilly and Co.
  • Used to treat acute leukemias and all lymphomas
  • Side effects include nervous system damage and constipation
  • Work is being done to develop more effective derivatives with fewer side effects8
how it works
How it works
  • Stops division of cells
  • Enters cell during mitosis and blocks formation of microtubules of the mitotic spindle during metaphase3,7
bibliography
Bibliography
  • (1) Anonymous Vincristine. In The Merck index: an encyclopedia of chemicals, drugs, and biologicals; O'Neil, M. J., Ed.; Merck: Whitehouse Station, NJ, 2006; pp 1717-1718.
  • (2) Anonymous Chemfinder.com Database and Internet Searching. http://chemfinder.cambridgesoft.com (accessed Jan. 22, 2007).
  • (3) Anonymous Overview: The Mitotic Spindle. http://www.sinauer.com/pdf/nsp-cellcycle-6-0.pdf (accessed Apr. 15, 2007).
  • (4) Choi, Y. H.; Kim, J.; Yoo, K. Supercritical Fluid Extraction and Liquid Chromatography-Electrospray Mass Analysis of Vinblastine from Catharanthus roseus. Chem. Pharm. Bull. 2002, 50, 1294--1296.
  • (5) Huhtikangas, A.; Laakso, I.; Seppaenen-Laakso, T.; Verma, A. Patent Application Country: Application: FI; Patent Country: FI Patent 107924, 2001.
  • (6) Kuboyama, T.; Yokoshima, S.; Tokuyama, H.; Fukuyama, T. Stereocontrolled total synthesis of (+)-vincristine. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 11966-11970.
  • (7) Lurie, P. M.; Manaster, J.; Stryckmans, P. A.; Vamecq, G. Mode of Action of Chemotherapy in vivo on Human Acute Leukemia--II. Vincristine. Europ. J. Cancer 1973, 9, 613--620.
  • (8) Szabo, L.; Bolcskei, H.; Eszter, B.; Mak, M.; Szantay, C. Synthesis of vinca alkaloids and related compounds, Part XCV: Nitration study of vinblastine-type bisindole alkaloids. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 339--405.