oclacitinib   Click here for help

GtoPdb Ligand ID: 9696

Synonyms: Apoquel® (veterinary use) | PF-03394197
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Oclacitinib is an oral pan-Janus kinase (JAK) inhibitor. It is approved as a veterinary drug for treating nonspecific allergic dermatitis and atopic dermatitis in dogs [2]. We drew the structure as depicted in the WHO INN record for oclacitinib. SMILES generated from the INN structure resolve to PubChem CID 44631938 through structure match, but note that this CID is a tautomer/isomer without specified stereochemistry. The oclacitinib structure also resolves to example 1A claimed in patent WO2010020905, in which the possibility of cis/trans isomers is noted [1]. Administered as oclacitinib maleate (PF-03394197-11, PubChem CID 44631937).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 99.36
Molecular weight 337.16
XLogP 1.9
No. Lipinski's rules broken 0
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Canonical SMILES CNS(=O)(=O)CC1CCC(CC1)N(c1[nH]cnc2c1ccn2)C
Isomeric SMILES CNS(=O)(=O)C[C@@H]1CC[C@H](CC1)N(c1[nH]cnc2c1ccn2)C
InChI InChI=1S/C15H23N5O2S/c1-16-23(21,22)9-11-3-5-12(6-4-11)20(2)15-13-7-8-17-14(13)18-10-19-15/h7-8,10-12,16H,3-6,9H2,1-2H3,(H,17,18,19)/t11-,12-
1. Berlinski PJ, Birchmeier MJ, Bowman JW, Gonzales AJ, Kamerling SG, Mann DW, Mitton-Fry MJ. (2010)
Pyrrolo[2,3-d]pyrimidine compounds.
Patent number: WO2010020905. Assignee: Pfizer Inc.. Priority date: 20/08/2008. Publication date: 25/02/2010.
2. Gonzales AJ, Bowman JW, Fici GJ, Zhang M, Mann DW, Mitton-Fry M. (2014)
Oclacitinib (APOQUEL(®)) is a novel Janus kinase inhibitor with activity against cytokines involved in allergy.
J Vet Pharmacol Ther, 37 (4): 317-24. [PMID:24495176]
3. Haugh IM, Watson IT, Alan Menter M. (2018)
Successful treatment of atopic dermatitis with the JAK1 inhibitor oclacitinib.
Proc (Bayl Univ Med Cent), 31 (4): 524-525. [PMID:30949000]