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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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/s1InChIKey
ZDZOTLJHXYCWBA-VCVYQWHSSA-NSmiles
CC(=O)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.