Docetaxel trihydrateProduct ingredient for Docetaxel
- Name
- Docetaxel trihydrate
- Drug Entry
- Docetaxel
Docetaxel is a clinically well established anti-mitotic chemotherapy medication used for the treatment of different types of cancer, including breast, ovarian, and non-small cell lung cancer. Docetaxel is a complex diterpenoid molecule and a semisynthetic analogue of paclitaxel.6,7 Docetaxel reversibly binds to microtubulin with high affinity in a 1:1 stoichiometric ratio, allowing it to prevent cell division and promote to cell death.6 Compared to paclitaxel, docetaxel is two times more potent as an inhibitor of microtubule depolymerization. Docetaxel binds to microtubules but does not interact with dimeric tubulin.5
The use of docetaxel may lead to udesired outcomes such as hepatic impairment, hematologic effects, enterocolitis and neutropenic colitis, hypersensitivity reactions, fluid retention, second primary malignancies, embryo-fetal toxicity, and tumor lysis syndrome.7 Docetaxel was approved by the FDA in 1996 and is available in solution for injection for intravenous or parenteral administration.6
- Accession Number
- DBSALT001786
- Structure
Structure for Docetaxel trihydrate (DBSALT001786)
- Synonyms
- Docetaxel (as trihydrate) / Docetaxel hydrate
- UNII
- 15H5577CQD
- CAS Number
- 148408-66-6
- Weight
- Average: 861.935
Monoisotopic: 861.378299444 - Chemical Formula
- C43H59NO17
- InChI Key
- XCDIRYDKECHIPE-QHEQPUDQSA-N
- 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
- 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[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate trihydrate
- SMILES
- O.O.O.[H][C@@]1(C[C@@]2(O)[C@@H](OC(=O)C3=CC=CC=C3)[C@]3([H])[C@@]4(CO[C@@H]4C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C(=C1C)C2(C)C)OC(C)=O)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1
- External Links
- ChemSpider
- 130580
- ChEBI
- 59809
- ChEMBL
- CHEMBL3545252
- Predicted Properties
Property Value Source Water Solubility 0.0127 mg/mL ALOGPS logP 2.59 ALOGPS logP 2.92 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 10.96 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 224.45 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 203.9 m3·mol-1 Chemaxon Polarizability 82.1 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon