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+
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form TH-4000E
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10229 tarloxotinib bromide
Synonyms Click here for help
PR610 | tarloxotinib cation | TH-4000
Database Links Click here for help
CAS Registry No. 1636938-13-0 (source: SciFinder)
GtoPdb PubChem SID 328083511
PubChem CID 51038316
Search Google for chemical match using the InChIKey MUJMYVFVAWFUJL-SNAWJCMRSA-O
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UniChem Compound Search for chemical match using the InChIKey MUJMYVFVAWFUJL-SNAWJCMRSA-O
UniChem Connectivity Search for chemical match using the InChIKey MUJMYVFVAWFUJL-SNAWJCMRSA-O