AZD4205   Click here for help

GtoPdb Ligand ID: 10744

Synonyms: AZD-4205 | 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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-N-[3-[2-[(3-methoxy-1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-1H-indol-7-yl]-2-(4-methylpiperazin-1-yl)propanamide
Synonyms Click here for help
AZD-4205 | compound 21 [PMID: 32297743] | example 32 [US9714236B2] [1] | JAK1-IN-3
Database Links Click here for help
BindingDB Ligand 264212
CAS Registry No. 2091134-68-6 (source: PubChem)
GtoPdb PubChem SID 405067336
PubChem CID 126715380
Search Google for chemical match using the InChIKey CVCVOSPZEVINRM-MRXNPFEDSA-N
Search Google for chemicals with the same backbone CVCVOSPZEVINRM
Search UniChem for chemical match using the InChIKey CVCVOSPZEVINRM-MRXNPFEDSA-N
Search UniChem for chemicals with the same backbone CVCVOSPZEVINRM