deucravacitinib   Click here for help

GtoPdb Ligand ID: 10432

Synonyms: BMS-986165 | BMS986165 | compound 11 [PMID: 31318208} | Sotyktu® | Tyk2-IN-4
Approved drug Immunopharmacology Ligand
deucravacitinib is an approved drug (FDA (2022), EMA (2023))
Compound class: Synthetic organic
Comment: Deucravacitinib (BMS-986165) is a selective, orally active, allosteric inhibitor of the Janus kinase family enzyme, tyrosine kinase 2 (TYK2) [2,5]. The deuteromethyl amide group confers selectivity by virtue of binding to a pocket in the TYK2 JH2 pseudokinase domain.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 135.95
Molecular weight 422.18
XLogP 1.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES CNC(=O)c1nnc(cc1Nc1cccc(c1OC)c1ncn(n1)C)NC(=O)C1CC1
Isomeric SMILES COc1c(cccc1c1ncn(n1)C)Nc1cc(nnc1C(=O)NC([2H])([2H])[2H])NC(=O)C1CC1
InChI InChI=1S/C20H22N8O3/c1-21-20(30)16-14(9-15(25-26-16)24-19(29)11-7-8-11)23-13-6-4-5-12(17(13)31-3)18-22-10-28(2)27-18/h4-6,9-11H,7-8H2,1-3H3,(H,21,30)(H2,23,24,25,29)/i1D3
InChI Key BZZKEPGENYLQSC-FIBGUPNXSA-N
No information available.
Summary of Clinical Use Click here for help
Deucravacitinib (BMS-986165) was advanced to evaluation in clinical studies in patients with systemic lupus erythematosus and ulcerative colitis (both Phase 2) and moderate-to-severe psoriasis (Phase 3) [3]. Click here to link to ClinicalTrials.gov's full list of BMS-986165 studies.
Deucravacitinib was granted full FDA approval in September 2022, as a treatment for moderate-to-severe plaque psoriasis (in adults).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02534636 Safety Study of BMS-986165 in Healthy Subjects and to Treat Psoriasis Phase 1 Interventional Bristol-Myers Squibb
NCT03624127 Effectiveness and Safety of BMS-986165 Compared to Placebo and Active Comparator in Participants With Psoriasis Phase 3 Interventional Bristol-Myers Squibb The POETYK PSO-1 study: deucravacitinib vs. placebo or active comparator apremilast [...].
NCT03611751 An Investigational Study to Evaluate Experimental Medication BMS-986165 Compared to Placebo and a Currently Available Treatment in Participants With Moderate-to-Severe Plaque Psoriasis Phase 3 Interventional Bristol-Myers Squibb The POETYK PSO-2 study [...].
NCT04036435 Long-Term Study That Measures the Safety and Efficacy of Deucravacitinib (BMS-986165) in Participants With Psoriasis Phase 3 Interventional Bristol-Myers Squibb A deucravacitinib long-term extension trial (POETYK PSO-LTE) in patients from POETYK PSO-1 and 2.