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
SMILES / InChI / InChIKey
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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-
InChI Key HJWLJNBZVZDLAQ-HAQNSBGRSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
9469 oclacitinib
Synonyms Click here for help
Apoquel® (veterinary use) | PF-03394197
Database Links Click here for help
BindingDB Ligand 185700
ChEMBL Ligand CHEMBL2103874
GtoPdb PubChem SID 348353655
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