serlopitant   Click here for help

GtoPdb Ligand ID: 9280

Synonyms: compound 17 (Jiang et al. 2009) [1] | VPD-737
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Serlopitant is a potent, brain-penetrant neurokinin (NK1) receptor antagonist [1], being investigated for antiinflammatory action. It has more favourable pharmacology than the approved NK1 antagonist aprepitant.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 29.54
Molecular weight 555.2
XLogP 7.15
No. Lipinski's rules broken 1
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Canonical SMILES O=C1CCC(=C1)N1CC2C(C1)C(C(CC2)OC(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)c1ccc(cc1)F
Isomeric SMILES O=C1CCC(=C1)N1C[C@@H]2[C@@H](C1)[C@@H]([C@H](CC2)O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)c1ccc(cc1)F
InChI InChI=1S/C29H28F7NO2/c1-16(19-10-20(28(31,32)33)12-21(11-19)29(34,35)36)39-26-9-4-18-14-37(23-7-8-24(38)13-23)15-25(18)27(26)17-2-5-22(30)6-3-17/h2-3,5-6,10-13,16,18,25-27H,4,7-9,14-15H2,1H3/t16-,18-,25-,26+,27+/m1/s1
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Summary of Clinical Use Click here for help
Serlopitant (VPD-737) is being evaluated in Phase 2 clinical trials for efficacy against chronic treatment resistant pruritus and itch associated with epidermolysis bullosa and prurigo nodularis.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
NK1 antagonists inhibit substance-P-evoked IP-1 formation, thereby decreasing the maximal response to substance P.