paclitaxel   Click here for help

GtoPdb Ligand ID: 2770

Synonyms: 7-epipaclitaxel | Abraxane® (albumin-bound suspension) | Taxol®
Approved drug PDB Ligand
paclitaxel is an approved drug (FDA (1992), EMA (2008))
Comment: Paclitaxel is a tubulin inhibitor. It was originally identified and isolated from the bark of the Pacific yew, Taxus brevifolia (hence the name 'taxol', and naming of the taxane family of compounds- includes docetaxel and cabazitaxel). The drug can be administered as a solvent-based drug, or in a formulation called nab-paclitaxel. Nab-paclitaxel consists of paclitaxel bound to albumin nanoparticles as a delivery vehicle (trade name Abraxane)- nab stands for nanoparticle albumin-bound.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 4
Rotatable bonds 15
Topological polar surface area 221.29
Molecular weight 853.33
XLogP 2.96
No. Lipinski's rules broken 2
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Canonical SMILES CC(=O)OC1C(=O)C2(C)C(O)CC3C(C2C(C2(C(C1=C(C)C(OC(=O)C(C(c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
Isomeric SMILES CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)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)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
InChI InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
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Summary of Clinical Use Click here for help
Solvent-based paclitaxel is approved to treat lung, ovarian and breast cancers and Kaposi's sarcoma.
Nab-paclitaxel is designated as an orphan drug by the US FDA, for the treatment of metastatic adenocarcinoma of the pancreas (in combination with gemcitabine). It is fully approved for this indication and for use in certain breast cancer patients (with tumours unresponsive to other chemotherapy, or relapsed disease) and non-small-cell lung cancer (NSCLC).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Paclitaxel binds to the β-subunit of tubulin, which prevents the microtubule/paclitaxel complex from disassembling. This prevents normal microtubulin growth and function by stopping the microtubules from shortening and lengthening as they normally would.
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