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+
1. Schmieder GJ, Draelos ZD, Pariser DM, Banfield C, Cox L, Hodge M, Kieras E, Parsons-Rich D, Menon S, Salganik M et al.. (2018)
Efficacy and safety of the Janus kinase 1 inhibitor PF-04965842 in patients with moderate-to-severe psoriasis: phase II, randomized, double-blind, placebo-controlled study.
Br J Dermatol, 179 (1): 54-62. [PMID:28949012]
2. Silverberg JI, Simpson EL, Thyssen JP, Gooderham M, Chan G, Feeney C, Biswas P, Valdez H, DiBonaventura M, Nduaka C et al.. (2020)
Efficacy and Safety of Abrocitinib in Patients With Moderate-to-Severe Atopic Dermatitis: A Randomized Clinical Trial.
JAMA Dermatol, 156 (8): 863-873. [PMID:32492087]
3. Simpson EL, Sinclair R, Forman S, Wollenberg A, Aschoff R, Cork M, Bieber T, Thyssen JP, Yosipovitch G, Flohr C et al.. (2020)
Efficacy and safety of abrocitinib in adults and adolescents with moderate-to-severe atopic dermatitis (JADE MONO-1): a multicentre, double-blind, randomised, placebo-controlled, phase 3 trial.
Lancet, 396 (10246): 255-266. [PMID:32711801]
4. Vazquez ML, Kaila N, Strohbach JW, Trzupek JD, Brown MF, Flanagan ME, Mitton-Fry MJ, Johnson TA, TenBrink RE, Arnold EP et al.. (2018)
Identification of N-{cis-3-[Methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclobutyl}propane-1-sulfonamide (PF-04965842): A Selective JAK1 Clinical Candidate for the Treatment of Autoimmune Diseases.
J Med Chem, 61 (3): 1130-1152. [PMID:29298069]