Tirbanibulin information

Tirbanibulin
Clinical data
Trade names	Klisyri, Onakta
Other names	KX2-391
AHFS/Drugs.com	Monograph
License data	US DailyMed: Tirbanibulin;
Pregnancy; category	AU: D; ;
Routes of; administration	Topical
Drug class	Microtubule inhibitor
ATC code	D06BX03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only;
Identifiers
	IUPAC name N-benzyl-2-[5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridin-2-yl]acetamide;
CAS Number	897016-82-9;
PubChem CID	23635314;
DrugBank	DB06137;
ChemSpider	24633341;
UNII	4V9848RS5G;
KEGG	D11691;
ChEMBL	ChEMBL571546;
PDB ligand	DN0 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID30237862 ;
ECHA InfoCard	100.305.161
Chemical and physical data
Formula	C26H29N3O3
Molar mass	431.536 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Cc1ccc(-c2ccc(OCCN3CCOCC3)cc2)cn1)NCc1ccccc1;
	InChI InChI=1S/C26H29N3O3/c30-26(28-19-21-4-2-1-3-5-21)18-24-9-6-23(20-27-24)22-7-10-25(11-8-22)32-17-14-29-12-15-31-16-13-29/h1-11,20H,12-19H2,(H,28,30); Key:HUNGUWOZPQBXGX-UHFFFAOYSA-N;

Tirbanibulin, sold under the brand name Klisyri, is a medication used for the treatment of actinic keratosis (AKs) on the face or scalp.^[4]^[5]^[6] It functions as a mitotic inhibitor by inhibiting tubulin polymerization and Src kinase signaling.^[7] It is potentially effective in deferring the development of AKs to squamous cell carcinoma in situ.^[8]

The most common side effects include local skin reactions, application site pruritus, and application site pain.^[4]^[5]

Tirbanibulin was approved for medical use in the United States in December 2020,^[5]^[9]^[10] and in the European Union in July 2021.^[6] The US Food and Drug Administration (FDA) considers it to be a first-in-class medication.^[11]

^ ^a ^b "Onakta APMDS". Therapeutic Goods Administration (TGA). 6 March 2024. Retrieved 7 March 2024.
^ "Summary Basis of Decision for Onakta". Health Canada. 20 July 2023. Archived from the original on 10 March 2024. Retrieved 4 October 2023.
^ "Details for: Onakta". Health Canada. 12 May 2023. Archived from the original on 10 March 2024. Retrieved 4 October 2023.
^ ^a ^b ^c "Klisyri- tirbanibulin ointment". DailyMed. Archived from the original on 11 January 2021. Retrieved 8 January 2021.
^ ^a ^b ^c ^d Cite error: The named reference FDA snapshot was invoked but never defined (see the help page).
^ ^a ^b ^c "Klisyri EPAR". European Medicines Agency (EMA). 20 April 2021. Archived from the original on 23 July 2021. Retrieved 22 July 2021. Text was copied from this source which is © European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
^ Niu L, Yang J, Yan W, Yu Y, Zheng Y, Ye H, et al. (November 2019). "Reversible binding of the anticancer drug KXO1 (tirbanibulin) to the colchicine-binding site of β-tubulin explains KXO1's low clinical toxicity". The Journal of Biological Chemistry. 294 (48): 18099–18108. doi:10.1074/jbc.RA119.010732. PMC 6885616. PMID 31628188.
^ Dao DD, Sahni VN, Sahni DR, Balogh EA, Grada A, Feldman SR (April 2022). "1% Tirbanibulin Ointment for the Treatment of Actinic Keratoses". The Annals of Pharmacotherapy. 56 (4): 494–500. doi:10.1177/10600280211031329. PMC 8899810. PMID 34301153.
^ "Drug Approval Package: Klisyri". U.S. Food and Drug Administration (FDA). 28 December 2020. Archived from the original on 12 January 2021. Retrieved 8 January 2021.
^ "Athenex Announces FDA Approval of Klisyri (Tirbanibulin) for the Treatment of Actinic Keratosis on the Face or Scalp" (Press release). Athenex Inc. 15 December 2020. Archived from the original on 19 December 2020. Retrieved 15 December 2020 – via GlobeNewswire.
^ "New Drug Therapy Approvals 2020". U.S. Food and Drug Administration (FDA). 31 December 2020. Archived from the original on 18 January 2021. Retrieved 17 January 2021.

[Onakta_APMDS-1] "Onakta APMDS". Therapeutic Goods Administration (TGA). 6 March 2024. Retrieved 7 March 2024.

[2] "Summary Basis of Decision for Onakta". Health Canada. 20 July 2023. Archived from the original on 10 March 2024. Retrieved 4 October 2023.

[3] "Details for: Onakta". Health Canada. 12 May 2023. Archived from the original on 10 March 2024. Retrieved 4 October 2023.

[Klisyri_FDA_label-4] "Klisyri- tirbanibulin ointment". DailyMed. Archived from the original on 11 January 2021. Retrieved 8 January 2021.

[FDA_snapshot-5] Cite error: The named reference FDA snapshot was invoked but never defined (see the help page).

[Klisyri_EPAR-6] "Klisyri EPAR". European Medicines Agency (EMA). 20 April 2021. Archived from the original on 23 July 2021. Retrieved 22 July 2021. Text was copied from this source which is © European Medicines Agency. Reproduction is authorized provided the source is acknowledged.

[NiuYang2019-7] Niu L, Yang J, Yan W, Yu Y, Zheng Y, Ye H, et al. (November 2019). "Reversible binding of the anticancer drug KXO1 (tirbanibulin) to the colchicine-binding site of β-tubulin explains KXO1's low clinical toxicity". The Journal of Biological Chemistry. 294 (48): 18099–18108. doi:10.1074/jbc.RA119.010732. PMC 6885616. PMID 31628188.

[:02-8] Dao DD, Sahni VN, Sahni DR, Balogh EA, Grada A, Feldman SR (April 2022). "1% Tirbanibulin Ointment for the Treatment of Actinic Keratoses". The Annals of Pharmacotherapy. 56 (4): 494–500. doi:10.1177/10600280211031329. PMC 8899810. PMID 34301153.

[9] "Drug Approval Package: Klisyri". U.S. Food and Drug Administration (FDA). 28 December 2020. Archived from the original on 12 January 2021. Retrieved 8 January 2021.

[10] "Athenex Announces FDA Approval of Klisyri (Tirbanibulin) for the Treatment of Actinic Keratosis on the Face or Scalp" (Press release). Athenex Inc. 15 December 2020. Archived from the original on 19 December 2020. Retrieved 15 December 2020 – via GlobeNewswire.

[11] "New Drug Therapy Approvals 2020". U.S. Food and Drug Administration (FDA). 31 December 2020. Archived from the original on 18 January 2021. Retrieved 17 January 2021.

Tirbanibulin information

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