docetaxel

Also known as Docecad®, EmDOC, Taxotere®, TXL, N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel, N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol, docetaxel, anhydrous

Docetaxel (DTX or DXL), sold under the brand name Taxotere among others, is a chemotherapy medication used to treat a number of types of cancer. This includes breast cancer, head and neck cancer, stomach cancer, prostate cancer and non-small-cell lung cancer. It may be used by itself or along with other chemotherapy medication. It is given by slow injection into a vein.

Chemical data

Formula: C43H53NO14
Molecular weight: 807.9 g/mol
IUPAC name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)O
InChIKey: ZDZOTLJHXYCWBA-VCVYQWHSSA-N
XLogP: 1.6
Polar surface area: 224 Å²
H-bond donors: 5
H-bond acceptors: 14
Formal charge: 0

via PubChem

Research

22,864 papers

Docetaxel.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 1995
Docetaxel remodels prostate cancer immune microenvironment and enhances checkpoint inhibitor-based immunotherapy.Theranostics · 2022
Docetaxel as a Model Compound to Promote HDL (High-Density Lipoprotein) Biogenesis and Reduce Atherosclerosis.Arteriosclerosis, thrombosis, and vascular biology · 2023
Docetaxel-induced Flagellate Erythema - Case Report and Brief Review.Current drug safety · 2023
The interactions of docetaxel with tumor microenvironment.International immunopharmacology · 2023

via PubMed

Wikidata facts

Mass: 807.347

Show 5 more facts

chemical formula: C₄₃H₅₃NO₁₄
isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)O
canonical SMILES: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)O
Commons category: Docetaxel
stylized name: DOCEtaxel

Sources (7)

via Wikidata · CC0

~27 min read

Article

22 sections

Contents

Medical uses
Outcomes
Breast cancer
Monitoring and combination use
Side effects
Contraindications and patient factors
Pregnancy
Drug interactions
Chemistry
Formulations and compositions
Active regions
Pharmacokinetics
Absorption and distribution
Metabolism and excretion
Mechanism of action
Molecular target
Modes of action
Cellular responses
Society and culture
Discovery, regulation and marketing
Costs
References

{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461754129 | image = Docetaxel.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Docetaxel-from-xtal-3D-sk.png | image_class2 = bg-transparent | width2 = 250 | alt2 =