cabazitaxel   Click here for help

GtoPdb Ligand ID: 6798

Synonyms: Jevanta® | taxoid XRP6258 | TXD 258 | XRP-6258
Approved drug
cabazitaxel is an approved drug (FDA (2010), EMA (2011))
Compound class: Synthetic organic
Comment: Cabazitaxel is a pan tubulin inhibitor of the taxane class of compounds.
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View more information in the IUPHAR Pharmacology Education Project: cabaitaxel

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 3
Rotatable bonds 16
Topological polar surface area 202.45
Molecular weight 835.38
XLogP 3.01
No. Lipinski's rules broken 2
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Canonical SMILES COC1C(=O)C2(C)C(OC)CC3C(C2C(C2(C(C1=C(C)C(OC(=O)C(C(c1ccccc1)NC(=O)OC(C)(C)C)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
Isomeric SMILES CO[C@H]1C(=O)[C@]2(C)[C@@H](OC)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)OC(C)(C)C)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
InChI 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
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Summary of Clinical Use Click here for help
Used in combination with prednisone to treat prostate cancer that has progressed after treatment with other anti-cancer medicines, including docetaxel.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Like docetaxel, cabazitaxel reversibly binds to microtubules with high affinity, hyper-stabilising their structure and limiting the flexibility of the cell's cytoskeleton, thus compromising cell growth, division and ultimately viability.