cabazitaxel

Also known as Jevanta®, taxoid XRP6258, TXD 258, XRP-6258, Cabazitaxelum, Taxoid XRP6258, TXD258

Cabazitaxel, sold under the brand name Jevtana, is a semi-synthetic derivative of a natural taxoid. It is a microtubule inhibitor, and the fourth taxane to be approved as a cancer therapy.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 460123299
Drug.image: Cabazitaxel2DACS.svg
Drug.image_class: skin-invert-image
Drug.tradename: Jevtana
Drug.MedlinePlus: a611009
Drug.DailyMedID: Cabazitaxel
Drug.pregnancy_AU: D
Drug.routes_of_administration: Intravenous
Drug.ATC_prefix: L01
Drug.ATC_suffix: CD04
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only
Drug.CAS_number: 183133-96-2

via Wikipedia infobox

Chemical data

Formula: C45H57NO14
Molecular weight: 835.9 g/mol
IUPAC name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-9,12-dimethoxy-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)OC)C)OC
InChIKey: BMQGVNUXMIRLCK-OAGWZNDDSA-N
XLogP: 2.7
Polar surface area: 202 Å²
H-bond donors: 3
H-bond acceptors: 14
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2010
Admin. routes: parenteral
Indications: dedifferentiated liposarcoma, neoplasm, prostate carcinoma, small cell lung carcinoma

via ChEMBL · EBI

Research

1,476 papers

[(177)Lu]Lu-PSMA-617 versus cabazitaxel in patients with metastatic castration-resistant prostate cancer (TheraP): a randomised, open-label, phase 2 trial.Lancet (London, England) · 2021
Prednisone plus cabazitaxel or mitoxantrone for metastatic castration-resistant prostate cancer progressing after docetaxel treatment: a randomised open-label trial.Lancet (London, England) · 2010
Cabazitaxel versus Abiraterone or Enzalutamide in Metastatic Prostate Cancer.The New England journal of medicine · 2019
Cabazitaxel plus carboplatin for the treatment of men with metastatic castration-resistant prostate cancers: a randomised, open-label, phase 1-2 trial.The Lancet. Oncology · 2019
Overall survival with [(177)Lu]Lu-PSMA-617 versus cabazitaxel in metastatic castration-resistant prostate cancer (TheraP): secondary outcomes of a randomised, open-label, phase 2 trial.The Lancet. Oncology · 2024

via PubMed

Wikidata facts

Mass: 835.377906
Has use: medication

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chemical formula: C₄₅H₅₇NO₁₄
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)OC)C)OC
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)OC)C)OC
World Health Organisation international non-proprietary name: cabazitaxel
medical condition treated: prostate cancer
legal status (medicine): boxed warning
significant drug interaction: idelalisib
Commons category: Cabazitaxel

Sources (8)

via Wikidata · CC0

~5 min read

Encyclopedic overview

7 sections

Contents

Medical uses
Mechanism of action
Clinical trials
Pharmacokinetics
Metabolism
References
External links

{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460123299 | image = Cabazitaxel2DACS.svg | image_class = skin-invert-image | width = | alt = | caption =

Excerpted from Wikipedia’s “cabazitaxel” article, available under the CC BY-SA 4.0 licence.

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