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Substance Name: Docetaxel [INN]
RN: 114977-28-5
UNII: 699121PHCA
InChIKey: ZDZOTLJHXYCWBA-VCVYQWHSSA-N

Note

  • 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

Molecular Weight

  • 807.8847
 

Classification Codes

  • Antimitotic Agents
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Mitosis Modulators
  • Tubulin Modulators
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Names and Synonyms

Results Name

  • Docetaxel [INN]

Name of Substance

  • Docetaxel
  • Docetaxel anhydrous
  • Docetaxel [INN]

Synonyms

  • Docefrez
  • Docetaxel
  • Docetaxel Winthrop
  • Docetaxol
  • Docetaxolum
  • Docetaxolum [INN-Latin]
  • HSDB 6965
  • N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyltaxol
  • NSC 628503
  • RP 56976
  • RP-56976
  • SID 530
  • Taxoel
  • Taxotere
  • UNII-699121PHCA
  • 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,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (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
  • 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-ylester, (2aR-(2a-alpha,4-beta,4a-beta,6-beta,9-alpha(alpha-R*,beta-S*),11-alpha,12-alpha,12a-alpha,12b-alpha))-

Registry Numbers

CAS Registry Number

  • 114977-28-5

FDA UNII

  • 699121PHCA

Other Registry Numbers

  • 129522-72-1
  • 216252-50-5

System Generated Number

  • 0114977285

Structure Descriptors

InChI

InChI=1S/C43H53NO14/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)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1

InChIKey

ZDZOTLJHXYCWBA-VCVYQWHSSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 2500ug/kg (2.5mg/kg)   Seminars in Oncology. Vol. 22(Suppl,
man TDLo intravenous 24mg/kg/9W-I (24mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS

PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE

BEHAVIORAL: MUSCLE WEAKNESS		 Annals of Oncology. Vol. 8, Pg. 187, 1997.
mouse LD50 intravenous 156mg/kg (156mg/kg)   Seminars in Oncology. Vol. 22(Suppl,
rat LDLo intravenous 20mg/kg (20mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 39, Pg. 659, 1997.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 232 deg C   EXP
log P (octanol-water) 2.830 (none)   EST
Water Solubility 0.025 mg/L 25 EST
Vapor Pressure 1.90E-28 mm Hg 25 EST
Henry's Law Constant 8.10E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.20E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.