Substance

ID:449181

Names and Identifiers
IUPAC name
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate
Synonyms
YewtaxanAnzataxPaclitaxelTaxol A
IUPAC Traditional name
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate
Registration numbers
CAS Number
Properties
Product Information
Application(s)
Antileukaemic and antineoplastic agent, esp. against melanoma and ovarian tumours
Use limited by low solubility and scarce availability of Taxus brevifolia bark
Biochemical tool extensively used to study cellular shape and function.
Also shown to be active against oomycete fungi
Biological Source
Isol. from the stem bark of Taxus brevifolia and Taxus cuspidata (Taxaceae)
Pharmacology Properties
Mechanism of Action
Interferes with the normal function of microtubule growth by hyper-stabilisation of their structure
Binds to the beta subunit of tubulin
Molecule Details
No Data Available
Click here to submit data
Molecular Spectra
No Data Available
Click here to submit data
References
• Kingston, D.G.I. et al., J. Nat. Prod., 1982, 45, 466-470, (2',7-di-Ac)
• Horwitz, S.B. et al., Ann. N.Y. Acad. Sci., 1986, 466, 733, (rev, pharmacol)
• Kingston, D.G.I., Pharmacol. Ther., 1991, 52, 1, (rev, pharmacol)
• Joel, S.P., Chem. Ind. (London), 1994, 172, (rev)
• Kingston, D.G.I. et al., J. Nat. Prod., 1990, 53, 1; 802, (bibl, rev)
• Williams, H.J. et al., Tetrahedron, 1993, 49, 6545, (pmr, conformn)
• Suffness, M. et al., Alkaloids (N.Y.), 1985, 25, 10, (rev, pharmacol)
• Slichenmyer, W.J. et al., Anti-Cancer Drugs, 1991, 2, 519, (rev)
• Fleming, P.E. et al., J.A.C.S., 1993, 115, 805, (biosynth)
• Young, D.H. et al., Experientia, 1992, 48, 882, (antifungal activity)
• Horwitz, S.B., Trends Pharmacol. Sci., 1992, 13, 134, (rev)
• Wall, M.E., Chron. Drug Discovery, 1993, 3, 327, (rev)
• Hoke, S.H. et al., J. Nat. Prod., 1994, 57, 277, (ms)
• Wani, M.S. et al., J.A.C.S., 1971, 93, 2325, (isol, nmr, ms, ir, uv)
• Falzone, C.J. et al., Tet. Lett., 1992, 33, 1169, (pmr, cmr)
• Ojima, I. et al., Tetrahedron, 1992, 48, 6985, (synth)
• Wheeler, N.C. et al., J. Nat. Prod., 1992, 55, 432, (occur)
• Hilton, B.D. et al., J. Nat. Prod., 1992, 55, 1157, (pmr)
• Stierle, A. et al., Science (Washington, D.C.), 1993, 260, 214, (isol, ms)
• Rose, W.C., Anti-Cancer Drugs, 1992, 3, 311, (rev)
• Winkler, J.D. et al., Tetrahedron, 1992, 48, 6953, (rev)
• Nicolaou, K.C. et al., Angew. Chem., Int. Ed., 1994, 33, 15, (rev)
• Huang, C.H.O. et al., J. Nat. Prod., 1986, 49, 665, (isol, deriv)
• Blechert, S. et al., Alkaloids (N.Y.), 1990, 39, 195, (rev, pharmacol)
• Potier, P., Chem. Soc. Rev., 1992, 21, 113, (rev)
• Chmurny, G.N. et al., J. Nat. Prod., 1992, 55, 414, (pmr, cmr)
• Zhang, H. et al., Yunnan Zhiwu Yanjiu, 1993, 15, 424; CA, 121, 78282e
• Sonnichsen, D.S. et al., Clin. Pharmacokinet., 1994, 27, 256, (rev, pharmacokinet)
• Hongjie, Z. et al., Heterocycles, 1994, 38, 975
• Gimon, M.E. et al., J. Nat. Prod., 1994, 57, 1404, (ms)
• Nicolaou, K.C. et al., Nature (London), 1994, 367, 630, (synth)
• Nicolaou, K.C. et al., J.A.C.S., 1995, 117, 624; 634; 645; 653, (synth)
• Taxol: Science and Applications, Ed., Suffness, M, CRC Press, Boca Raton, USA, 1995, (book)
• Shiina, I. et al., Chem. Lett., 1998, 3-4, (synth)
• Mukaiyama, T. et al., Chem. Eur. J., 1999, 5, 121-161, (Taxol, synth, rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 556
• Kerns, E.H. et al., J. Nat. Prod., 1994, 57, 1391, (ms)
• Fleming, P.E. et al., Pure Appl. Chem., 1994, 66, 2045, (biosynth)
• Kingston, D.G.I. et al., Tet. Lett., 1994, 35, 4483, (synth)
• Nogales, E. et al., Nature (London), 1995, 375, 424
• Danishefsky, S.J. et al., J.A.C.S., 1996, 118, 2843, (synth)
• Heinstein, P. et al., J.C.S. Perkin 1, 1996, 845, (ms)
• Gao, Q. et al., Acta Cryst. C, 1995, 51, 295, (cryst struct)
• Rowinsky, E.K. et al., N. Engl. J. Med., 1995, 332, 1004, (use, tox, rev)
• Wender, P.A. et al., J.A.C.S., 1997, 119, 2757, (synth)
• Gennari, C. et al., J.O.C., 1997, 62, 4746-4755, (synth)
• Kusama, H. et al., J.A.C.S., 2000, 122, 3811-3820, (synth)
• Huizing, M.T. et al., J. Chromatogr., B: Biomed. Appl., 1995, 664, 373, (hplc)
• Baloglu, E. et al., J. Nat. Prod., 1999, 62, 1068-1071, (synth)
• Vyas, D.M. et al., Prog. Med. Chem., 1995, 32, 289, (rev)
• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 655, (bibl, synth)
• Walker, K. et al., Phytochemistry, 2001, 58, 1-7, (biosynth, rev)
• The Chemistry and Pharmacology of Taxol(R) and its Derivatives, (Ed. Farina, V.), Elsevier, 1995, (book)
• Gao, Q. et al., Tetrahedron, 1996, 52, 2291, (cryst struct)
• Eisenhauer, E.A. et al., Drugs, 1998, 55, 5-30, (pharmacol, rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TAH775
• Holton, R.A. et al., J.A.C.S., 1994, 116, 1597; 1599, (synth)
• Fleming, P.E. et al., J.A.C.S., 1994, 116, 4137, (biosynth)
• Georg, G.I. et al., ACS Symp. Ser., 1995, 583, (book)
• Grothaus, P.G. et al., J. Nat. Prod., 1995, 58, 1003, (immunoassay)
• Rao, K.V., J. Het. Chem., 1997, 34, 675-680, (synth)
• Hezari, M. et al., Planta Med., 1997, 63, 291-295, (biosynth, rev)
• Ranson, M. et al., Expert Opin. Invest. Drugs, 1999, 8, 837-848
• Das, B. et al., Indian J. Chem., Sect. B, 1999, 38, 1018-1024, (rev)