Structure via PubChem · Public domain (PubChem)
cabazitaxel
Sign in to saveAlso 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.
In the Vinony graph
Vinony's link graph records 281 inbound references to cabazitaxel, and connects out to prostate cancer, tiazofurin and digital object identifier.
It sits within the topics Acetate esters, Benzoate esters and Carbamates.
Vinony links it to 22 Wikipedia language editions.
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 Ų
- 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
Show 8 more facts
- 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 sectionsContents
- 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 =
| pronounce = | tradename = Jevtana | Drugs.com = | MedlinePlus = a611009 | DailyMedID = Cabazitaxel | pregnancy_AU = D | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Intravenous | class = | ATC_prefix = L01 | ATC_suffix = CD04 | ATC_supplemental =
Excerpted from Wikipedia’s “cabazitaxel” article, available under the CC BY-SA 4.0 licence.