(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 127178
• Molecular Formular: C43H53NO14
• Molecular Mass: 807.87922
• Monoisotopic Mass: 807.34660538
• SMILES: O=C(OC(C)(C)C)N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@@H]1C(=C2[C@@H](O)C(=O)[C@]3([C@H]([C@H](OC(=O)c4ccccc4)[C@@](O)(C2(C)C)C1)[C@@]1(OC(=O)C)[C@H](OC1)C[C@@H]3O)C)C
• Canonical SMILES: CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H]([C@H](c3ccccc3)NC(=O)OC(C)(C)C)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: docetaxel
• Brand Name: Taxotere
• Synonyms: Docetaxel; Taxotere®; Docetaxel

Database IDs

• CAS Number: 114977-28-5
• MDL Number: MFCD00800737
• PubChem SID: 162221500; 24845209
• PubChem CID: 148124
• CHEBI ID: 4672
• ATC CODE: L01CD02
• CHEMBL: 92
• Chemspider ID: 130581
• DrugBank ID: DB01248
• KEGG ID: D07866
• Unique Ingredient Identifier: 699121PHCA
• Wikipedia Title: Docetaxel
• Medline Plus: a696031

CALCULATED PROPERTIES

• Acid pKa: 10.957364
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 2.9167895
• LogD (pH = 7.4): 2.9166708
• Log P: 2.916791
• Molar Refractivity: 203.9017 cm^3
• Polarizability: 81.427376 Å^3
• Polar Surface Area: 224.45 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Do you have solubility information on this product that you would like to share?
• Melting Point: 186-192 °C (dec.)

Safety Information

• RTECS: DA4172750
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: IV
• Bioavailability: NA
• Excretion: Biliary
• Half Life: 86 hours
• Metabolism: Hepatic
• Protein Bound: >98%
• Legal Status: Rx-only
• Pregnancy Category: D (US)

Product Information

• Purity: ≥97.0% (HPLC)
• Grade: purum
• Impurities: ~6% water
• Empirical Formula (Hill Notation): C43H53NO14

DETAILS

Sigma Aldrich - 01885

Frequently Asked Questions
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Application
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Docetaxel can be used to study antibiotics, cell biology, cell signaling, neuroscience and apoptosis and the cell cycle. Docetaxel has been used to study the prevention of chemotherapy-induced alopecia, as well as the treatment of non-small-cell lung cancer in patients contraindicated for standard chemotherapy. Docetaxel has also been used to study the role of hypoxia-inducible factor-1α and -2α in androgen insensitive prostate cancer cells.
Biochem/physiol Actions
Docetaxel is a taxane anti-cancer agent related to paclitaxel. It binds to and stabilizes the β-tubulin subunit of microtubules, preventing depolymerization of the mitotic spindle thus leading to cell cycle arrest and apoptosis.