tariquidar   Click here for help

GtoPdb Ligand ID: 11787

Synonyms: compound 2 [PMID: 10098671] | XR-9576 | XR9576
PDB Ligand
Compound class: Synthetic organic
Comment: Tariquidar (XR9576) is a third generation inhibitor of the ATP-binding cassette transporter P-glycoprotein (P-gp; ABCB1) [1]. P-gp is a drug transporter that can promote resistance to drugs, including chemotherapeutics. Pharmacologic inhibition of P-gp is an established strategy that is being investigated to block this resistance mechanism in cancers [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 13
Topological polar surface area 111.25
Molecular weight 646.28
XLogP 5.35
No. Lipinski's rules broken 2
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Canonical SMILES COc1cc(C(=O)Nc2ccc(cc2)CCN2CCc3c(C2)cc(c(c3)OC)OC)c(cc1OC)NC(=O)c1cnc2c(c1)cccc2
Isomeric SMILES COc1c(cc2CN(CCc2c1)CCc1ccc(cc1)NC(=O)c1cc(c(cc1NC(=O)c1cc2ccccc2nc1)OC)OC)OC
InChI InChI=1S/C38H38N4O6/c1-45-33-18-25-14-16-42(23-28(25)19-34(33)46-2)15-13-24-9-11-29(12-10-24)40-38(44)30-20-35(47-3)36(48-4)21-32(30)41-37(43)27-17-26-7-5-6-8-31(26)39-22-27/h5-12,17-22H,13-16,23H2,1-4H3,(H,40,44)(H,41,43)
1. Fox E, Bates SE. (2007)
Tariquidar (XR9576): a P-glycoprotein drug efflux pump inhibitor.
Expert Rev Anticancer Ther, 7 (4): 447-59. [PMID:17428165]
2. Lai JI, Tseng YJ, Chen MH, Huang CF, Chang PM. (2020)
Clinical Perspective of FDA Approved Drugs With P-Glycoprotein Inhibition Activities for Potential Cancer Therapeutics.
Front Oncol, 10: 561936. [PMID:33312947]
3. Roe M, Folkes A, Ashworth P, Brumwell J, Chima L, Hunjan S, Pretswell I, Dangerfield W, Ryder H, Charlton P. (1999)
Reversal of P-glycoprotein mediated multidrug resistance by novel anthranilamide derivatives.
Bioorg Med Chem Lett, 9 (4): 595-600. [PMID:10098671]