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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H57NO14.C3H6O
Molecular Weight 894.0115
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABAZITAXEL ACETONE

SMILES

CC(C)=O.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=JXGFNOAMBPABCK-JVXKREHESA-N
InChI=1S/C45H57NO14.C3H6O/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;1-3(2)4/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52);1-2H3/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+;/m0./s1

HIDE SMILES / InChI

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

Molecular Formula C3H6O
Molecular Weight 58.0791
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:46:30 UTC 2019
Edited
by admin
on Mon Oct 21 23:46:30 UTC 2019
Record UNII
9JX5MZ1I64
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CABAZITAXEL ACETONE
WHO-DD  
Common Name English
CABAZITAXEL ACETONE [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
72734356
Created by admin on Mon Oct 21 23:46:30 UTC 2019 , Edited by admin on Mon Oct 21 23:46:30 UTC 2019
PRIMARY
EVMPD
SUB180105
Created by admin on Mon Oct 21 23:46:30 UTC 2019 , Edited by admin on Mon Oct 21 23:46:30 UTC 2019
PRIMARY
CAS
1426815-65-7
Created by admin on Mon Oct 21 23:46:30 UTC 2019 , Edited by admin on Mon Oct 21 23:46:30 UTC 2019
PRIMARY
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