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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H57NO14
Molecular Weight 835.9324
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABAZITAXEL

SMILES

CO[C@H]1C[C@H]2OC[C@@]2(OC(C)=O)[C@H]3[C@H](OC(=O)C4=CC=CC=C4)[C@]5(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C6=CC=CC=C6)C(C)=C([C@@H](OC)C(=O)[C@]13C)C5(C)C

InChI

InChIKey=BMQGVNUXMIRLCK-OAGWZNDDSA-N
InChI=1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1

HIDE SMILES / InChI

Description

Cabazitaxel (JEVTANA®) is an antineoplastic agent belonging to the taxane class and is used to treat people with prostate cancer that has progressed despite treatment with docetaxel. It is prepared by semi-synthesis with a precursor extracted from yew needles (10-deacetylbaccatin III). Cabazitaxel (JEVTANA®) is a microtubule inhibitor. It binds to tubulin and promotes its assembly into microtubules while simultaneously inhibiting disassembly. This leads to the stabilization of microtubules, which results in the inhibition of mitotic and interphase cellular functions. The cell is then unable to progress further into the cell cycle, being stalled at metaphase, thus triggering apoptosis of the cancer cell.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
JEVTANA KIT
PubMed

PubMed

TitleDatePubMed
Cabazitaxel.
2010 Sep
Cabazitaxel (jevtana): a novel agent for metastatic castration-resistant prostate cancer.
2012 Aug
Quantification of cabazitaxel, its metabolite docetaxel and the determination of the demethylated metabolites RPR112698 and RPR123142 as docetaxel equivalents in human plasma by liquid chromatography-tandem mass spectrometry.
2013 Apr 15
Molecular alterations and emerging targets in castration resistant prostate cancer.
2014 Mar
Patents

Sample Use Guides

In Vivo Use Guide
JEVTANA® 25 mg/m2 administered every three weeks as a one-hour intravenous infusion in combination with oral prednisone 10 mg administered daily throughout JEVTANA® treatment.
Route of Administration: Intravenous
In Vitro Use Guide
Cabazitaxel and docetaxel were tested in vitro against the cancer cell line panel at concentrations from 0.01 to 0.1 uM and in vivo against a subset of the solid tumor xenograft models at a dose of 10 or 7.5 mg/kg on an every 4 days × 3 I.V. schedule. In vitro, both cabazitaxel and docetaxel had similar potency (median relative IC50 0.47 nM and 0.88 nM, respectively) and a similar activity profile, with Ewing sarcoma cells being significantly more sensitive to both agents. In vitro sensitivity to docetaxel inversely correlated with mRNA expression for ABCB1, but the correlation with ABCB1 expression was weaker for cabazitaxel. In vivo cabazitaxel demonstrated significantly greater activity than docetaxel in five of 12 tumor models, inducing regressions in six models compared with three models for docetaxel.
Name Type Language
CABAZITAXEL
EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
TXD 258
Code English
CABAZITAXEL [MI]
Common Name English
CABAZITAXEL ACETONATE [JAN]
Common Name English
XRP 6258
Code English
CABAZITAXEL [EMA EPAR]
Common Name English
CABAZITAXEL [USAN]
Common Name English
CABAZITAXEL [VANDF]
Common Name English
CABAZITAXEL [MART.]
Common Name English
CABAZITAXEL [ORANGE BOOK]
Common Name English
1-HYDROXY-7.BETA.,10.BETA.-DIMETHOXY-9-OXO-5.BETA.,20-EPOXYTAX-11-ENE-2.ALPHA.,4,13.ALPHA.-TRIYL 4-ACETATE 2-BENZOATE 13-((2R,3S)-3-(((TERT-BUTOXY)CARBONYL)AMINO)-2-HYDROXY-3-PHENYLPROPANOATE)
Common Name English
XRP-6258
Code English
CABAZITAXEL [WHO-DD]
Common Name English
TXD-258
Code English
CABAZITAXEL [INN]
Common Name English
JEVTANA
Brand Name English
Classification Tree Code System Code
NDF-RT N0000175085
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
NDF-RT N0000175592
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
NCI_THESAURUS C67437
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
WHO-ATC L01CD04
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
EMA ASSESSMENT REPORTS JETVANA (AUTHORIZED: PROSTATIC, NEOPLASMS)
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
NCI_THESAURUS C1490
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
LIVERTOX 134
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
WHO-VATC QL01CD04
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
Code System Code Type Description
MESH
C552428
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
DRUG BANK
DB06772
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
CAS
183133-96-2
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
PUBCHEM
9854073
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
EPA CompTox
183133-96-2
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
RXCUI
996051
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
CABAZITAXEL
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
MERCK INDEX
M2874
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1201748
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
NCI_THESAURUS
C66937
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
IUPHAR
6798
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
EVMPD
SUB31282
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY
INN
8967
Created by admin on Mon Oct 21 20:39:18 UTC 2019 , Edited by admin on Mon Oct 21 20:39:18 UTC 2019
PRIMARY