fevipiprant   Click here for help

GtoPdb Ligand ID: 8995

Synonyms: NVP-QAW039 | QAW039
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Fevipiprant is an orally available, selective antagonist of the prostanoid DP2 receptor (CRTh2) with anti-inflammatory action [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 97.64
Molecular weight 426.09
XLogP 3.73
No. Lipinski's rules broken 0
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Canonical SMILES OC(=O)Cc1c(C)n(c2c1cccn2)Cc1ccc(cc1C(F)(F)F)S(=O)(=O)C
Isomeric SMILES OC(=O)Cc1c(C)n(c2c1cccn2)Cc1ccc(cc1C(F)(F)F)S(=O)(=O)C
InChI InChI=1S/C19H17F3N2O4S/c1-11-15(9-17(25)26)14-4-3-7-23-18(14)24(11)10-12-5-6-13(29(2,27)28)8-16(12)19(20,21)22/h3-8H,9-10H2,1-2H3,(H,25,26)
1. Gonem S, Berair R, Singapuri A, Hartley R, Laurencin MFM, Bacher G, Holzauer B, Bourne M, Mistry V, Pavord ID et al.. (2016)
Fevipiprant, a prostaglandin D2 receptor 2 antagonist, in patients with persistent eosinophilic asthma: a single-centre, randomised, double-blind, parallel-group, placebo-controlled trial.
The Lancet,.
2. Sykes D, Bradley M, Riddy D, Willard L, Powell-Herlaar E, Sandham D, Watson S, Bauer C, Dubois G, Charlton S. (2014)
QAW039, a slowly dissociating CRTh2 antagonist with potential for improved clinical efficacy.
Eur Respir J, 44 (Supl 58): 4074.
3. Sykes DA, Bradley ME, Riddy DM, Willard E, Reilly J, Miah A, Bauer C, Watson SJ, Sandham DA, Dubois G et al.. (2016)
Fevipiprant (QAW039), a Slowly Dissociating CRTh2 Antagonist with the Potential for Improved Clinical Efficacy.
Mol Pharmacol, 89 (5): 593-605. [PMID:26916831]