petesicatib   Click here for help

GtoPdb Ligand ID: 9855

Synonyms: RG-7625 | RG7625 | RO-5459072
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Petesicatib is the INN for a cathepsin S inhibitor. The structure (and CAS registry number) submitted to the WHO match PubChem CID 59543597, and this ties the INN together with the research code RO5459072 assigned by Hoffman-La Roche to their cathepsin S inhibitor [2-3]. This same chemical structure is claimed in Hoffmann-La Roche patent WO2010121918A1, where it is example 238 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 133.54
Molecular weight 603.14
XLogP 2.97
No. Lipinski's rules broken 0
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Canonical SMILES N#CC1(CC1)NC(=O)C1CC(CN1C(=O)C1(CC1)C(F)(F)F)S(=O)(=O)c1ccc(cc1C(F)(F)F)c1cnn(c1)C
Isomeric SMILES N#CC1(CC1)NC(=O)[C@@H]1C[C@H](CN1C(=O)C1(CC1)C(F)(F)F)S(=O)(=O)c1ccc(cc1C(F)(F)F)c1cnn(c1)C
InChI InChI=1S/C25H23F6N5O4S/c1-35-11-15(10-33-35)14-2-3-19(17(8-14)24(26,27)28)41(39,40)16-9-18(20(37)34-22(13-32)4-5-22)36(12-16)21(38)23(6-7-23)25(29,30)31/h2-3,8,10-11,16,18H,4-7,9,12H2,1H3,(H,34,37)/t16-,18+/m1/s1
1. Alvarez SR, Banner D, Ceccerelli SM, Grether U, Haap W, Hartman P, Hartman G, Hilpert H, Kuehne H, Mauser H et al.. (2010)
Proline derivatives as cathepsin inhibitors.
Patent number: WO2010121918A1. Assignee: F. Hoffmann-La Roche Ag. Priority date: 20/04/2009. Publication date: 28/10/2010.
2. Tato M, Kumar SV, Liu Y, Mulay SR, Moll S, Popper B, Eberhard JN, Thomasova D, Rufer AC, Gruner S et al.. (2017)
Cathepsin S inhibition combines control of systemic and peripheral pathomechanisms of autoimmune tissue injury.
Sci Rep, 7 (1): 2775. [PMID:28584258]
3. Theron M, Bentley D, Nagel S, Manchester M, Gerg M, Schindler T, Silva A, Ecabert B, Teixeira P, Perret C et al.. (2017)
Pharmacodynamic Monitoring of RO5459072, a Small Molecule Inhibitor of Cathepsin S.
Front Immunol, 8: 806. [PMID:28769925]