golidocitinib   Click here for help

GtoPdb Ligand ID: 10744

Synonyms: AZD-4205 | AZD4205 | compound 21 [PMID: 32297743] | example 32 [US9714236B2] [1] | JAK1-IN-3
Compound class: Synthetic organic
Comment: AZD4205 is a selective, orally bioavailable, ATP-competitive inhibitor of Janus kinase 1 (JAK1) that was developed by Dizal Pharmaceutical Company [2]. It has been shown to enhance antitumour activity in combination with osimertinib (an approved EGFR inhibitor) in a preclinical non-small cell lung cancer xenograft model. A higher drug concentration within the gastrointestinal tract relative to plasma in preclinical models suggests potential to treat inflammatory bowel disease. Persistently activated STAT3 has been shown to be oncogenic, and drives expression of cellular proteins which contribute to central processes in cancer progression (survival, proliferation, invasion, angiogenesis). JAK1 is the key Janus kinase responsible for cytokine-mediated STAT3 activation.
The chemical structure of AZD4205 matches that for the INN golidocitinib which was surfaced in WHO Proposed list 125 in July 2021.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 116.23
Molecular weight 489.26
XLogP 1.86
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1nn(cc1Nc1nccc(n1)c1c[nH]c2c1cccc2NC(=O)[C@H](N1CCN(CC1)C)C)C
Isomeric SMILES COc1nn(cc1Nc1nccc(n1)c1c[nH]c2c1cccc2NC(=O)[C@H](N1CCN(CC1)C)C)C
InChI InChI=1S/C25H31N9O2/c1-16(34-12-10-32(2)11-13-34)23(35)28-20-7-5-6-17-18(14-27-22(17)20)19-8-9-26-25(29-19)30-21-15-33(3)31-24(21)36-4/h5-9,14-16,27H,10-13H2,1-4H3,(H,28,35)(H,26,29,30)/t16-/m1/s1
InChI Key CVCVOSPZEVINRM-MRXNPFEDSA-N
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Molecular structure representations generated using Open Babel