ziritaxestat   Click here for help

GtoPdb Ligand ID: 9561

Synonyms: compound 11 [PMID: 28414242] | GLPG-1690 | GLPG1690
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Ziritaxestat (GLPG1690) is a selective autotaxin Inhibitor [3], that was investigated for anti-fibrotic efficacy. Animal studies using GLPG1690 suggested potential for autotaxin inhibition in breast cancer treatment [2,9] and TSC2-loss associated oncogenicity (in tuberous sclerosis complex) [4]. In early 2021 data from the phase 3 ziritaxestat program in idiopathic pulmonary fibrosis (IPF; ISABELA) was analysed, and the conclusion reached was that ziritaxestat's benefit-risk profile did not support continuing the program. At that time the decision was made to discontinue the inhibitor's phase 2 trial in systemic sclerosis.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 132.48
Molecular weight 588.24
XLogP 3.62
No. Lipinski's rules broken 0
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Canonical SMILES CCc1nc2n(c1N(c1sc(c(n1)c1ccc(cc1)F)C#N)C)cc(cc2C)N1CCN(CC1)CC(=O)N1CC(C1)O
Isomeric SMILES CCc1nc2n(c1N(c1sc(c(n1)c1ccc(cc1)F)C#N)C)cc(cc2C)N1CCN(CC1)CC(=O)N1CC(C1)O
InChI InChI=1S/C30H33FN8O2S/c1-4-24-29(35(3)30-34-27(25(14-32)42-30)20-5-7-21(31)8-6-20)39-15-22(13-19(2)28(39)33-24)37-11-9-36(10-12-37)18-26(41)38-16-23(40)17-38/h5-8,13,15,23,40H,4,9-12,16-18H2,1-3H3
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
11017 ziritaxestat
Synonyms Click here for help
compound 11 [PMID: 28414242] | GLPG-1690 | GLPG1690
Database Links Click here for help
CAS Registry No. 1628260-79-6 (source: PubChem)
ChEMBL Ligand CHEMBL3828074
GtoPdb PubChem SID 336446947
PubChem CID 90420193
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UniChem Compound Search for chemical match using the InChIKey REQQVBGILUTQNN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey REQQVBGILUTQNN-UHFFFAOYSA-N