Title: Paclitaxel
CAS Registry Number: 33069-62-4
CAS Name: (aR,bS)-b-(Benzoylamino)-a-hydroxybenzenepropanoic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester
Additional Names: 5b,20-epoxy-1,2a,4,7b,10b,13a-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine; taxol A
Manufacturers' Codes: NSC-125973
Trademarks: Anzatax (Faulding); Paxene (Ivax); Taxol (BMS)
Molecular Formula: C47H51NO14
Molecular Weight: 853.91
Percent Composition: C 66.11%, H 6.02%, N 1.64%, O 26.23%
Literature References: Antiproliferative agent first isolated, as the l-form, from the bark of the Pacific yew tree, Taxus brevifolia, Taxaceae; promotes the assembly of microtubules and inhibits the tubulin disassembly process. Isoln and structure: M. C. Wani et al., J. Am. Chem. Soc. 93, 2325 (1971). In vitro promotion of microtubule assembly: P. B. Schiff et al., Nature 277, 665 (1979). Isoln from Taxus baccala L. and in vitro inhibition of depolymerization of microtubules into tubulin: G. Chauviere et al., C.R. Seances Acad. Sci. Ser. 2 293, 501 (1981). Total synthesis of taxusin, which contains the entire ring skeleton: R. A. Holton et al., J. Am. Chem. Soc. 110, 6558 (1988). Total stereosynthesis: R. A. Holton et al., ibid. 116, 1597, 1599 (1994); K. C. Nicolaou et al., Nature 367, 630 (1994). Production by Taxomyces andreanae, an endophytic fungus associated with T. brevifolia: A. Stierle et al., Science 260, 214 (1993). Review of mechanism of action: J. J. Manfredi, S. B. Horwitz, Pharmacol. Ther. 25, 83-125 (1984); S. B. Horwitz et al., Ann. N.Y. Acad. Sci. 466, 733-744 (1986); S. B. Horwitz, Trends Pharmacol. Sci. 13, 134-136 (1992). Symposium on clinical toxicology, pharmacology and efficacy: Semin. Oncol. 20, Suppl. 3, 1-60 (1993). Review of clinical experience in cancer therapy: T. M. Mekhail, M. Markman, Expert. Opin. Pharmacother. 3, 755-766 (2002). Clinical trial in prevention of coronary artery restenosis: G. W. Stone et al., N. Engl. J. Med. 350, 221 (2004).
Properties: Needles from aq methanol, mp 213-216° (dec). [a]D20 -49° (methanol). uv max (methanol): 227, 273 nm (e 29800, 1700).
Melting point: mp 213-216° (dec)
Optical Rotation: [a]D20 -49° (methanol)
Absorption maximum: uv max (methanol): 227, 273 nm (e 29800, 1700)
Use: Tool in study of structure and function of microtubules.
Therap-Cat: Antineoplastic; antirestenotic.
Keywords: Antineoplastic; Alkaloids/Natural Products; Taxanes; Antirestenotic. |