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Substance Name: Docetaxel [USAN:USP:INN:BAN]
RN: 148408-66-6
UNII: 15H5577CQD
InChIKey: XCDIRYDKECHIPE-QHEQPUDQSA-N

Notes

  • Semisynthetic analog of taxol.
  • Semisynthetic analog of taxol. NCI: A semi-synthetic, second-generation taxane derived from a compound found in the European yew tree Taxus baccata. Docetaxel displays potent and broad antineoplastic properties; it binds to and stabilizes tubulin, thereby inhibiting microtubule disassembly which results in cell- cycle arrest at the G2/M phase and cell death. This agent also inhibits pro-angiogenic factors such as vascular endothelial growth factor (VEGF) and displays immunomodulatory and pro-inflammatory properties by inducing various mediators of the inflammatory response. Docetaxel has been studied for use as a radiation-sensitizing agent. (NCI Thesaurus

Molecular Formula

  • C43-H53-N-O14.3H2-O

Molecular Weight

  • 861.9291
 

Classification Codes

  • Antimitotic Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Mitosis Modulators
  • Tubulin Modulators

Names and Synonyms

Name of Substance

  • Docetaxel [USAN:USP:INN:BAN]

MeSH Heading

  • Docetaxel

Synonyms

  • (2R,3S)-N-Carboxy-3-phenylisoserine, N-tert-butyl ester, 13-ester with 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4-acetate 2-benzoate, trihydrate
  • Docetaxel
  • RP 56976
  • Taxotere
  • UNII-15H5577CQD
  • XRP6976

Systematic Names

  • Benzenepropanoic acid, beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxy-, (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,8,1313-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, trihydrate, (alphaR,betaS)-
  • Benzenepropanoic acid, beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxy-, 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 trihydrate, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS),11alpha,12alpha,12aalpha,12balpha))-

Registry Numbers

CAS Registry Number

  • 148408-66-6

FDA UNII

  • 15H5577CQD

System Generated Number

  • 0148408666

Molecular Formulas

Molecular Formula

  • C43-H53-N-O14.3H2-O

Molecular Formula Fragments

  • C43-H53-N-O14
  • COMPONENT
  • H2-O

Structure Descriptors

InChI

InChI=1S/C43H53NO14.3H2O/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45;;;/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52);3*1H2/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+;;;/m0.../s1

InChIKey

XCDIRYDKECHIPE-QHEQPUDQSA-N

Smiles

O.O.O.CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@]3(C)[C@@H]2[C@H](OC(=O)c4ccccc4)[C@]5(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c6ccccc6)C(=C([C@@H](O)C3=O)C5(C)C)C