DF2755A   Click here for help

GtoPdb Ligand ID: 12230

Synonyms: DF 2755A | DF-2755A
Compound class: Synthetic organic
Comment: DF2755A inhibits CXCL8 (IL-8) signalling via its endogenous chemokine receptors CXCR1 and CXCR2 [2]. It does not alter the binding affinity of CXCL8 for either receptor, indicating that it is behaving as a negative allosteric modulator (NAM). Activation of the IL-8 pathway has been linked to the development of chemotherapy-induced neuropathic pain. It is predicted that inhibition of this mechanism might offer clinical utility for cancer patients who experience chemotherapy-induced peripheral neuropathy [1].
We show the carboxylic acid parent form for this compound, but DF2755A is used as the sodium salt.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 90.46
Molecular weight 316.3
XLogP 2.7
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES C[C@@H](c1ccc(cc1)Nc1scc(n1)C(F)(F)F)C(=O)O
Isomeric SMILES C[C@H](C(=O)O)c1ccc(Nc2nc(cs2)C(F)(F)F)cc1
InChI InChI=1S/C13H11F3N2O2S/c1-7(11(19)20)8-2-4-9(5-3-8)17-12-18-10(6-21-12)13(14,15)16/h2-7H,1H3,(H,17,18)(H,19,20)/t7-/m0/s1
1. Brandolini L, Castelli V, Aramini A, Giorgio C, Bianchini G, Russo R, De Caro C, d'Angelo M, Catanesi M, Benedetti E et al.. (2019)
DF2726A, a new IL-8 signalling inhibitor, is able to counteract chemotherapy-induced neuropathic pain.
Sci Rep, 9 (1): 11729. [PMID:31409858]
2. Lopes AH, Brandolini L, Aramini A, Bianchini G, Silva RL, Zaperlon AC, Verri Jr WA, Alves-Filho JC, Cunha FQ, Teixeira MM et al.. (2016)
DF2755A, a novel non-competitive allosteric inhibitor of CXCR1/2, reduces inflammatory and post-operative pain.
Pharmacol Res, 103: 69-79. [PMID:26592483]