AMG487   Click here for help

GtoPdb Ligand ID: 13071

Synonyms: AMG 487 | AMG-487 | compound 47 [PMID: 17448658]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AMG487 is a small molecule CXCR3 antagonist [2-3]. It was investigated for activity as a tumour metastasis inhibitor, based on evidence that CXCR3 expressed on tumour cells directly promotes metastasis [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 0
Rotatable bonds 12
Topological polar surface area 96.16
Molecular weight 603.59
XLogP 1.97
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCOC1=CC=C(C=C1)N2C(=NC3=NC=CC=C3C2=O)C(C)N(CC4=CC=CN=C4)C(=O)CC5=CC=C(C=C5)OC(F)(F)F
Isomeric SMILES CCOC1=CC=C(C=C1)N2C(=O)C3=C(N=CC=C3)N=C2C(C)N(CC4=CN=CC=C4)C(=O)CC5=CC=C(C=C5)OC(F)(F)F
InChI InChI=1S/C32H28F3N5O4/c1-3-43-25-14-10-24(11-15-25)40-30(38-29-27(31(40)42)7-5-17-37-29)21(2)39(20-23-6-4-16-36-19-23)28(41)18-22-8-12-26(13-9-22)44-32(33,34)35/h4-17,19,21H,3,18,20H2,1-2H3
InChI Key WQTKNBPCJKRYPA-UHFFFAOYSA-N
References
1. Bakheet SA, Ansari MA, Nadeem A, Attia SM, Alhoshani AR, Gul G, Al-Qahtani QH, Albekairi NA, Ibrahim KE, Ahmad SF. (2019)
CXCR3 antagonist AMG487 suppresses rheumatoid arthritis pathogenesis and progression by shifting the Th17/Treg cell balance.
Cell Signal, 64: 109395. [PMID:31449849]
2. Jiao H, Pang B, Chiang YC, Chen Q, Pan Q, Ren R, Hu H. (2023)
Structure basis for the modulation of CXC chemokine receptor 3 by antagonist AMG487.
Cell Discov, 9 (1): 119. [PMID:38012179]
3. Johnson M, Li AR, Liu J, Fu Z, Zhu L, Miao S, Wang X, Xu Q, Huang A, Marcus A et al.. (2007)
Discovery and optimization of a series of quinazolinone-derived antagonists of CXCR3.
Bioorg Med Chem Lett, 17 (12): 3339-43. [PMID:17448658]
4. Walser TC, Rifat S, Ma X, Kundu N, Ward C, Goloubeva O, Johnson MG, Medina JC, Collins TL, Fulton AM. (2006)
Antagonism of CXCR3 inhibits lung metastasis in a murine model of metastatic breast cancer.
Cancer Res, 66 (15): 7701-7. [PMID:16885372]