tarloxotinib   Click here for help

GtoPdb Ligand ID: 9409

Synonyms: PR610 | tarloxotinib cation | TH-4000
Compound class: Synthetic organic
Comment: Tarloxotinib (TH-4000) is a hypoxia-activated prodrug (HAP) [1] being developed by Threshold Pharmaceuticals. Delivered as the bromide salt (PubChem CID 51038315) as described in its INN record. The compound undergoes activation selectively within the hypoxic tumour compartment to produce an irreversible pan-ErbB tyrosine-kinase inhibitor, represented by TH-4000E [1]. The 4-nitroimidazole trigger on the tertiary amine side chain facilitates activation. This is one of the first molecularly targeted HAPs to be developed.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 140.76
Molecular weight 600.09
XLogP 3.45
No. Lipinski's rules broken 0
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Canonical SMILES O=C(Nc1ncc2c(c1)c(ncn2)Nc1ccc(c(c1)Br)Cl)C=CC[N+](Cc1n(C)cnc1[N+](=O)[O-])(C)C
Isomeric SMILES O=C(Nc1ncc2c(c1)c(ncn2)Nc1ccc(c(c1)Br)Cl)/C=C/C[N+](Cc1n(C)cnc1[N+](=O)[O-])(C)C
InChI InChI=1S/C24H23BrClN9O3/c1-33-14-30-24(34(37)38)20(33)12-35(2,3)8-4-5-22(36)32-21-10-16-19(11-27-21)28-13-29-23(16)31-15-6-7-18(26)17(25)9-15/h4-7,9-11,13-14H,8,12H2,1-3H3,(H-,27,28,29,31,32,36)/p+1/b5-4+
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Molecular structure representations generated using Open Babel