Deucravacitinib

Deucravacitinib
Clinical data
Pronunciation	/duːˌkrævəˈsɪtɪnɪb/; doo-KRA-və-SI-ti-nib
Trade names	Sotyktu
Other names	BMS-986165
Routes of; administration	By mouth
ATC code	L04AA56 (WHO) ;
Legal status
Legal status	US: ℞-only;
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-(Cyclopropanecarbonylamido)-4-[2-methoxy-3-(1-methyl-1,2,4-triazol-3-yl)anilino]-N- (trideuteriomethyl)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	C20H22N8O3
Molar mass	422.449 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, sold under the brand name Sotyktu, is a TYK2 inhibitor used for the treatment of moderate to severe plaque psoriasis.^[1] It was developed by Bristol Myers Squibb.^[2]

Mechanism of action

It acts as a highly selective allosteric inhibitor of non-receptor tyrosine-protein kinase 2 (TYK2).^[3]

Molecule design

The chemical structure of deucravacitinib contains a methyl amide in which all three hydrogen atoms are replaced by deuterium.^[4]

References

^ ^a ^b "Sotyktu- deucravacitinib tablet, film coated". DailyMed. 9 September 2022. Archived from the original on 28 September 2022. Retrieved 27 September 2022.
^ "U.S. Food and Drug Administration Approves Sotyktu™ (deucravacitinib), Oral Treatment for Adults with Moderate-to-Severe Plaque Psoriasis". Business Wire (Press release). 10 September 2022. Archived from the original on 10 September 2022. Retrieved 10 September 2022.
^ 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.
^ 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.

External links

"Deucravacitinib". Drug Information Portal. U.S. National Library of Medicine.

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[Sotyktu_FDA_label-1] "Sotyktu- deucravacitinib tablet, film coated". DailyMed. 9 September 2022. Archived from the original on 28 September 2022. Retrieved 27 September 2022.

[2] "U.S. Food and Drug Administration Approves Sotyktu™ (deucravacitinib), Oral Treatment for Adults with Moderate-to-Severe Plaque Psoriasis". Business Wire (Press release). 10 September 2022. Archived from the original on 10 September 2022. Retrieved 10 September 2022.

[3] 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.

[4] 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.

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