paclitaxel   

GtoPdb Ligand ID: 2770

Synonyms: 7-epipaclitaxel | Abraxane® (albumin-bound suspension) | Taxol®
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
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
SMILES / InChI / InChIKey
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
InChI Key RCINICONZNJXQF-MZXODVADSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (1992), EMA (2008))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
International Nonproprietary Names
INN number INN
7052 paclitaxel
Synonyms
7-epipaclitaxel | Abraxane® (albumin-bound suspension) | Taxol®
Database Links
BindingDB Ligand 50001839
CAS Registry No. 33069-62-4 (source: Scifinder)
ChEBI CHEBI:45863
ChEMBL Ligand CHEMBL428647
DrugBank Ligand DB01229
DrugCentral Ligand 2044
GtoPdb PubChem SID 135652721
NURSA Ligand 10.1621/ZJSTGVJ65V
PubChem CID 36314
RCSB PDB Ligand TA1
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Wikipedia Paclitaxel