Structural Formula Vector Image
Title: Docetaxel
CAS Registry Number: 114977-28-5
CAS Name: (aR,bS)-b-[[(1,1-Dimethylethoxy)carbonyl]amino]-a-hydroxybenzenepropanoic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester
Additional Names: N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol
Manufacturers' Codes: NSC-628503; RP-56976
Trademarks: Taxotere (Aventis)
Molecular Formula: C43H53NO14
Molecular Weight: 807.88
Percent Composition: C 63.93%, H 6.61%, N 1.73%, O 27.73%
Literature References: Semisynthetic derivative of paclitaxel, q.v., prepd using a natural precursor, 10-deacetylbaccatin III, extracted from the needles of the European yew tree, Taxus baccata L., Taxaceae. Antimitotic agent that promotes the assembly of microtubules and inhibits their depolymerization to free tubulin. Prepn: M. Colin et al., EP 253738; eidem, US 4814470 (1988, 1989 both to Rhône-Poulenc Sante); L. Mangatal et al., Tetrahedron 45, 4177 (1989). Synthesis of the side chain: J.-N. Denis et al., J. Org. Chem. 56, 6939 (1991). Structure-activity study: F. Guéritte-Voegelein et al., J. Med. Chem. 34, 992 (1991). Cytotoxic activity and mechanism of action: I. Ringel, S. B. Horwitz, J. Natl. Cancer Inst. 83, 288 (1991). In vivo antitumor activity: M.-C. Bissery et al., Cancer Res. 51, 4845 (1991). HPLC determn: J. C. Vergniol et al., J. Chromatogr. 582, 273 (1992). Clinical pharmacokinetics and toxicology: J.-M. Extra et al., Cancer Res. 53, 1037 (1993). Clinical trials in prostate cancer: I. F. Tannock et al., N. Engl. J. Med. 351, 1502 (2004); D. P. Petrylak et al., ibid. 1513. Symposium on clinical experience: Semin. Oncol. 27, Suppl. 3, 1-29 (2000). Review of mechanism of action and combination therapies: R. S. Herbst, F. R. Khuri, Cancer Treat. Rev. 29, 407-415 (2003); of clinical studies in non-small cell lung cancer: A. M. Davies et al., Expert Opin. Pharmacother. 4, 553-565 (2003).
Properties: mp 232°. [a]D -36° (c = 0.74 in ethanol). uv max: 230, 275, 283 nm (e 14800, 1730, 1670).
Melting point: mp 232°
Optical Rotation: [a]D -36° (c = 0.74 in ethanol)
Absorption maximum: uv max: 230, 275, 283 nm (e 14800, 1730, 1670)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products; Taxanes.

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