Ziritaxestat

Ziritaxestat
Identifiers
	IUPAC name 2-[[2-ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile;
CAS Number	1628260-79-6;
PubChem CID	90420193;
IUPHAR/BPS	9561;
DrugBank	DB15403;
ChemSpider	58828502;
UNII	I02418V13W;
KEGG	D11844;
ChEMBL	ChEMBL3828074;
Chemical and physical data
Formula	C30H33FN8O2S
Molar mass	588.71 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC1=C(N2C=C(C=C(C2=N1)C)N3CCN(CC3)CC(=O)N4CC(C4)O)N(C)C5=NC(=C(S5)C#N)C6=CC=C(C=C6)F;
	InChI 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; Key:REQQVBGILUTQNN-UHFFFAOYSA-N;

Ziritaxestat is a small-molecule, selective autotaxin inhibitor that was investigated as a potential treatment for idiopathic pulmonary fibrosis (IPF).^[1] Initially showing promise in early-phase studies, ziritaxestat underwent evaluation in two large-scale phase 3 clinical trials, ISABELA 1 and ISABELA 2.^[1]^[2] These trials aimed to assess the efficacy and safety of ziritaxestat in patients with IPF, including those receiving standard of care treatment with pirfenidone or nintedanib.^[1] However, both trials were prematurely terminated due to a lack of efficacy, as ziritaxestat failed to demonstrate significant improvement in lung function or other clinical outcomes compared to placebo.^[1]^[2]^[3]

References

^ ^a ^b ^c ^d Maher TM, Ford P, Brown KK, Costabel U, Cottin V, Danoff SK, et al. (May 2023). "Ziritaxestat, a Novel Autotaxin Inhibitor, and Lung Function in Idiopathic Pulmonary Fibrosis: The ISABELA 1 and 2 Randomized Clinical Trials". JAMA. 329 (18): 1567–1578. doi:10.1001/jama.2023.5355. PMC 10170340. PMID 37159034.
^ ^a ^b Grossi G (16 May 2023). "Ziritaxestat Fails to Demonstrate Efficacy for Treatment of IPF in 2 Trials". HCPLive.
^ Spagnolo P, Maher TM (September 2024). "The future of clinical trials in idiopathic pulmonary fibrosis". Current Opinion in Pulmonary Medicine. 30 (5): 494–499. doi:10.1097/MCP.0000000000001099. PMC 11377049. PMID 38963152.

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[Maher_2023-1] Maher TM, Ford P, Brown KK, Costabel U, Cottin V, Danoff SK, et al. (May 2023). "Ziritaxestat, a Novel Autotaxin Inhibitor, and Lung Function in Idiopathic Pulmonary Fibrosis: The ISABELA 1 and 2 Randomized Clinical Trials". JAMA. 329 (18): 1567–1578. doi:10.1001/jama.2023.5355. PMC 10170340. PMID 37159034.

[HCPLive-2] Grossi G (16 May 2023). "Ziritaxestat Fails to Demonstrate Efficacy for Treatment of IPF in 2 Trials". HCPLive.

[Spagnolo_2024-3] Spagnolo P, Maher TM (September 2024). "The future of clinical trials in idiopathic pulmonary fibrosis". Current Opinion in Pulmonary Medicine. 30 (5): 494–499. doi:10.1097/MCP.0000000000001099. PMC 11377049. PMID 38963152.

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[2]

[3]

Identifiers

IUPAC name 2-[[2-ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile
CAS Number	1628260-79-6
PubChem CID	90420193
IUPHAR/BPS	9561
DrugBank	DB15403
ChemSpider	58828502
UNII	I02418V13W
KEGG	D11844
ChEMBL	ChEMBL3828074
Chemical and physical data
Formula	C₃₀H₃₃FN₈O₂S
Molar mass	588.71 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC1=C(N2C=C(C=C(C2=N1)C)N3CCN(CC3)CC(=O)N4CC(C4)O)N(C)C5=NC(=C(S5)C#N)C6=CC=C(C=C6)F
InChI 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 Key:REQQVBGILUTQNN-UHFFFAOYSA-N