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Monograph Number:  7052
Title:  Paclitaxel
CAS Registry Number:  33069-62-4
CAS Name:  [2aR-[2aa,4b,4ab,6b,9a(aR*,bS*),11a,12a,12aa,12ba]]-b-(Benzoylamino)-a-hydroxybenzenepropanoic acid 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 (Baker Norton);  Taxol (Bristol-Myers Squibb)
Molecular Formula:  C47H51NO14
Molecular Weight:  853.90.  
Percent Composition:  C 66.11%, H 6.02%, N 1.64%, O 26.23%
Literature References:  Antileukemic and antitumor 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. Acad. Sci. Paris Ser. II 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).  Synthesis and anticancer activity of derivs:  D. G. I. Kingston et al., Studies in Organic Chemistry vol. 26, entitled "New Trends in Natural Products Chemistry 1986", Atta-ur-Rahman, P. W. Le Quesne, Eds. (Elsevier, Amsterdam, 1986) pp 219-235.  Production by Taxomyces andreanae, an endophytic fungus associated with T. brevifolia:  A. Stierle et al., Science 260, 214 (1993).  Use in study of structure and function of microtubules:  S. B. Horwitz et al., Cold Spring Harbor Symp. Quant. Biol. 46, 219 (1982).  Clinical evaluation in Kaposi's sarcoma:  M. W. Saville et al., Lancet 346, 26 (1995).  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:  Sem. Oncol. 20, Suppl. 3, 1-60 (1993).  Review in ovarian cancer:  C. D. Runowicz et al., Cancer 71, 1591-1596 (1993).  Book:  Taxol?  Science and Applications, M. Suffness, Ed. (CRC Press, Boca Raton, 1995) 426 pp.
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.
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