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)
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
ABCB1 Mm Inhibitor Inhibition 7.4 pIC50 - 3
pIC50 7.4 (IC50 3.8x10-8 M) [3]
Description: Measuring the effect of XR9576 on accumulation of [3H] daunorubicin in the multidrug resistant mouse mammary carcinoma cell line EMT6/AR1.0