Deucravacitinib

Deucravacitinib, sold under the brand name Sotyktu, is a medication used for the treatment of moderate-to-severe plaque psoriasis.^[7] It is a tyrosine kinase 2 (TYK2) inhibitor and it is taken by mouth.^[7] It was developed by Bristol Myers Squibb.^[10]

Deucravacitinib

Clinical data
Pronunciation	/duːˌkrævəˈsɪtɪnɪb/ doo-KRA-və-SI-ti-nib
Trade names	Sotyktu
Other names	BMS-986165
AHFS/Drugs.com	Monograph
License data	US DailyMed: Deucravacitinib
Pregnancy category	AU: B1[1]
Routes of administration	By mouth
Drug class	Tyrosine kinase 2 (TYK2) inhibitor
ATC code	L04AF07 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[1][2] CA: ℞-only[3][4][5] UK: POM (Prescription only)[6] US: ℞-only[7] EU: Rx-only[8][9]
Pharmacokinetic data
Bioavailability	99%
Protein binding	82–90%
Metabolism	Liver (primarily CYP1A2)
Metabolites	BMT-153261 (active)
Elimination half-life	10 hours
Excretion	Feces, urine
Identifiers
IUPAC name 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1,2,4-triazol-3-yl)phenyl)amino)-N-(trideuteromethyl)pyridazine-3-carboxamide
CAS Number	1609392-27-9
PubChem CID	134821691
DrugBank	DB16650
ChemSpider	72380005
UNII	N0A21N6RAU
KEGG	D11817
ChEMBL	ChEMBL435170
ECHA InfoCard	100.329.069
Chemical and physical data
Formula	C20H19D3N8O3
Molar mass	425.466 g·mol−1
3D model (JSmol)	Interactive image
SMILES [2H]C([2H])([2H])NC(=O)C1=NN=C(C=C1NC2=CC=CC(=C2OC)C3=NN(C=N3)C)NC(=O)C4CC4
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 Key:BZZKEPGENYLQSC-FIBGUPNXSA-N

Deucravacitinib was approved for medical use in the United States in September 2022,^[7][11][12] and in Australia in December 2022.^[1] The US Food and Drug Administration (FDA) considers it to be a first-in-class medication.^[13][14]

Medical uses

Deucravacitinib is indicated for the treatment of adults with moderate-to-severe plaque psoriasis.^[7]

Mechanism of action

It acts as a highly selective allosteric inhibitor of non-receptor tyrosine-protein kinase 2 (TYK2).^[15]

Molecule design

The chemical structure of deucravacitinib contains a methyl amide in which all three hydrogen atoms are replaced by deuterium.^[16]

Society and culture

Legal status

In January 2023, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMA) adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Sotyktu, intended for the treatment of moderate to severe psoriasis.^[8][17] The applicant for this medicinal product is Bristol-Myers Squibb Pharma EEIG.^[8][17] Deucravacitinib was approved for medical use in the European Union in March 2023.^[8]

References

1. "Sotyktu". Therapeutic Goods Administration (TGA). 14 December 2022. Archived from the original on 9 June 2023. Retrieved 15 April 2023.
2. "Sotyktu (Bristol-Myers Squibb Australia Pty Ltd)". Therapeutic Goods Administration (TGA). 13 January 2023. Archived from the original on 27 March 2023. Retrieved 9 April 2023.
3. "Details for: Sotyktu". Health Canada. 14 February 2023. Archived from the original on 3 March 2024. Retrieved 3 March 2024.
4. "Notice: Multiple Additions to the Prescription Drug List (PDL) [2023-03-08]". Health Canada. 8 March 2023. Archived from the original on 22 March 2023. Retrieved 21 March 2023.
5. "Summary Basis of Decision - Sotyktu". Health Canada. 10 March 2023. Archived from the original on 25 April 2023. Retrieved 24 April 2023.
6. "Sotyktu Summary of Product Characteristics (SmPC)". (emc). 13 July 2023. Archived from the original on 20 December 2023. Retrieved 20 December 2023.
7. "Sotyktu- deucravacitinib tablet, film coated". DailyMed. 9 September 2022. Archived from the original on 28 September 2022. Retrieved 27 September 2022.
8. "Sotyktu EPAR". European Medicines Agency (EMA). 24 March 2023. Archived from the original on 19 February 2024. Retrieved 3 March 2024.
9. "Sotyktu". Union Register of medicinal products. 27 March 2023. Archived from the original on 31 March 2023. Retrieved 30 March 2023.
10. "U.S. Food and Drug Administration Approves Sotyktu (deucravacitinib), Oral Treatment for Adults with Moderate-to-Severe Plaque Psoriasis" (Press release). Bristol Myers Squibb. 10 September 2022. Archived from the original on 10 September 2022. Retrieved 10 September 2022 – via Business Wire.
11. "Drug Approval Package: Sotyktu". U.S. Food and Drug Administration (FDA). 14 October 2022. Archived from the original on 5 January 2023. Retrieved 4 January 2023.
12. Truong TM, Pathak GN, Singal A, Taranto V, Rao BK (June 2023). "Deucravacitinib: The First FDA-Approved Oral TYK2 Inhibitor for Moderate to Severe Plaque Psoriasis". The Annals of Pharmacotherapy. 58 (4): 416–427. doi:10.1177/10600280231153863. PMID 37341177. S2CID 259211735.
13. "Advancing Health Through Innovation: New Drug Therapy Approvals 2022". U.S. Food and Drug Administration (FDA). 10 January 2023. Archived from the original on 21 January 2023. Retrieved 22 January 2023. This article incorporates text from this source, which is in the public domain.
14. New Drug Therapy Approvals 2022 (PDF). U.S. Food and Drug Administration (FDA) (Report). January 2024. Archived from the original on 14 January 2024. Retrieved 14 January 2024. This article incorporates text from this source, which is in the public domain.
15. Chimalakonda A, Burke J, Cheng L, Catlett I, Tagen M, Zhao Q, et al. (October 2021). "Selectivity Profile of the Tyrosine Kinase 2 Inhibitor Deucravacitinib Compared with Janus Kinase 1/2/3 Inhibitors". Dermatology and Therapy. 11 (5): 1763–1776. doi:10.1007/s13555-021-00596-8. PMC 8484413. PMID 34471993.
16. Mullard A (September 2022). "First de novo deuterated drug poised for approval". Nature Reviews. Drug Discovery. 21 (9): 623–625. doi:10.1038/d41573-022-00139-6. PMID 35974147. S2CID 251623586.
17. "Sotyktu: Pending EC decision". European Medicines Agency (EMA). 26 January 2023. Archived from the original on 27 January 2023. Retrieved 28 January 2023.