abrocitinib   Click here for help

GtoPdb Ligand ID: 9991

Synonyms: Cibinqo® | compound 25 [PMID: 29298069] | PF-04965842 | PF04965842
Approved drug PDB Ligand Immunopharmacology Ligand
abrocitinib is an approved drug (UK, Japan & EMA (2021), FDA (2022))
Compound class: Synthetic organic
Comment: Abrocitinib (PF-04965842) is a JAK inhibitor [4]. X-ray crystal structures of PF-04965842 bound to both JAK1 and JAK2 have been deposited with the Protein DataBank (accession IDs 6BBU and 6BBV respectively). We used the SMILES string supplied with the article in which the structure was declared [4] to generate our representation of the chemical structure. The IUPAC name in abrocitinib's INN record resolves to the same StdInChIKey as our structure. PubChem CID 78323835 represents the structure without specified stereochemistry.
The JAKs are immunokinases that are molecular targets of therapeutics which are used in the treatment of immune-mediated diseases.
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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 6
Topological polar surface area 99.36
Molecular weight 323.14
XLogP 2.05
No. Lipinski's rules broken 0
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Canonical SMILES CCCS(=O)(=O)NC1CC(C1)N(c1ncnc2c1cc[nH]2)C
Isomeric SMILES CCCS(=O)(=O)N[C@@H]1C[C@@H](C1)N(c1ncnc2c1cc[nH]2)C
InChI InChI=1S/C14H21N5O2S/c1-3-6-22(20,21)18-10-7-11(8-10)19(2)14-12-4-5-15-13(12)16-9-17-14/h4-5,9-11,18H,3,6-8H2,1-2H3,(H,15,16,17)/t10-,11+
Immunopharmacology Comments
Abrocitinib (PF-04965842) is a JAK1-selective inhibitor that was advanced to clinical trial for the treatment of autoimmune diseases [1,4]. PF-04965842 exhibits 28-fold selectivity over JAK2, >340-fold over JAK3, and 43-fold over TYK2 at 1 mM ATP, and it shows a favourable selectivity profile over the broader kinome. It was approved for clinical use in 2021, by regulatory agencies in the UK, EU and Japan.
Immunopharmacology Disease
Disease X-Refs Comment References
Atopic dermatitis Disease Ontology: DOID:3310
OMIM: 603165
Approved drug for AD, which mediates immune suppression by inhibiting activity of the immunokinase JAK1.