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
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
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 |
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
PubMed
Title | Date | PubMed |
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Cabazitaxel. | 2010 Sep |
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Cabazitaxel (jevtana): a novel agent for metastatic castration-resistant prostate cancer. | 2012 Aug |
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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 |
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Molecular alterations and emerging targets in castration resistant prostate cancer. | 2014 Mar |
Sample Use Guides
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
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
Edited
Mon Oct 21 20:39:18 UTC 2019
by
admin
on
Mon Oct 21 20:39:18 UTC 2019
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Record UNII |
51F690397J
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175085
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NDF-RT |
N0000175592
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NCI_THESAURUS |
C67437
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WHO-ATC |
L01CD04
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EMA ASSESSMENT REPORTS |
JETVANA (AUTHORIZED: PROSTATIC, NEOPLASMS)
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NCI_THESAURUS |
C1490
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LIVERTOX |
134
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WHO-VATC |
QL01CD04
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Code System | Code | Type | Description | ||
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C552428
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DB06772
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183133-96-2
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9854073
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183133-96-2
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996051
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PRIMARY | RxNorm | ||
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CABAZITAXEL
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M2874
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PRIMARY | Merck Index | ||
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CHEMBL1201748
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C66937
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6798
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SUB31282
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8967
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Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
URINE
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TRANSPORTER -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
As cabazitaxel is mainly metabolized by CYP3A in vitro, strong CYP3A inducers or inhibitors are expected to affect the pharmacokinetics of cabazitaxel.
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
As cabazitaxel is mainly metabolized by CYP3A in vitro, strong CYP3A inducers or inhibitors are expected to affect the pharmacokinetics of cabazitaxel.
MAJOR
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
FECAL
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
by the CYP3A4/5 isoenzyme
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METABOLITE ACTIVE -> PARENT |
by the CYP3A4/5 isoenzyme
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METABOLITE ACTIVE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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intravenous infusion |
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blood-to-plasma ratio | PHARMACOKINETIC |
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