2-Cl-IB-MECA

• CAT Number: I002116
• CAS Number: 163042-96-4
• Molecular Formula: C18H18ClIN6O4
• Molecular Weight: 544.74
• Purity: ≥95%
• Target: Adenosine Receptor
• Solubility: DMSO ≥ 31 mg/mL
• Storage: 2-8°C
• IUPAC Name: (2S,3S,4R,5R)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• InChI: InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1
• InChIKey: IPSYPUKKXMNCNQ-PFHKOEEOSA-N
• SMILES: CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O

Namodenoson (Cat No.: I002116), also known as CF-102 and 2-Cl-IB-MECA, is a selective agonist of the A3 adenosine receptor (A3AR) with an impressively low Ki value of 0.33 nM. This compound has shown promise in the treatment of non-alcoholic steatohepatitis (NASH) by exerting its effects through the dysregulation of the PI3K/NF‑κB/Wnt/β‑catenin signaling pathway. Namodenoson’s ability to modulate these critical pathways makes it a significant focus of research in the development of potential therapies for NASH.

Reference

1:Stimulation of ANP secretion by 2-Cl-IB-MECA through A(3) receptor and CaMKII. Yuan K, Bai GY, Park WH, Kim SZ, Kim SH.Peptides. 2008 Dec;29(12):2216-24. doi: 10.1016/j.peptides.2008.09.003. Epub 2008 Sep 16. PMID: 18838091 2:The A3 adenosine receptor agonist 2-Cl-IB-MECA facilitates epileptiform discharges in the CA3 area of immature rat hippocampal slices. Laudadio MA, Psarropoulou C.Epilepsy Res. 2004 Apr-May;59(2-3):83-94. PMID: 15246113 3:A role for histamine in cytokine modulation by the adenosine A(3) receptor agonist, 2-Cl-IB-MECA. Smith SR, Denhardt G, Terminelli C.Eur J Pharmacol. 2002 Dec 13;457(1):57-69. PMID: 12460644 4:Hemodynamic effects and histamine release elicited by the selective adenosine A3 receptor agonist 2-Cl-IB-MECA in conscious rats. Van Schaick EA, Jacobson KA, Kim HO, IJzerman AP, Danhof M.Eur J Pharmacol. 1996 Jul 25;308(3):311-4. PMID: 8858305 Free PMC Article