Ensitrelvir

Ensitrelvir, sold under the brand name Xocova is an antiviral medication used as a treatment for COVID-19.[2][3][4][5] It was developed by Shionogi in partnership with Hokkaido University and acts as an orally active 3C-like protease inhibitor.[6][7] It is taken by mouth.[1][8][9]

Ensitrelvir
Clinical data
Trade namesXocova
Other namesS-217622
Routes of
administration		By mouth
ATC code
  • None
Legal status
Legal status
  • JP: Emergency approval[1]
Identifiers
  • 1-(2,4,5-Trifluorobenzyl)-3-[(1-methyl-1H-1,2,4-triazol-3-yl)methyl]-(6E)-6-[(6-chloro-2-methyl-2H-indazol-5-yl)imino]-1,3,5-triazinane-2,4-dione
CAS Number
PubChem CID
UNII
KEGG
Chemical and physical data
FormulaC22H17ClF3N9O2
Molar mass531.88 g·mol−1
3D model (JSmol)
  • Cn1cnc(CN2C(=O)N(Cc3cc(F)c(F)cc3F)C(=N\c3cc4cn(C)nc4cc3Cl)\NC2=O)n1
  • InChI=1S/C22H17ClF3N9O2/c1-32-7-12-4-18(13(23)5-17(12)30-32)28-20-29-21(36)35(9-19-27-10-33(2)31-19)22(37)34(20)8-11-3-15(25)16(26)6-14(11)24/h3-7,10H,8-9H2,1-2H3,(H,28,29,36)
  • Key:QMPBBNUOBOFBFS-UHFFFAOYSA-N
Xocova.Japanese blister pack

The most common adverse events include transient decreases in high-density lipoprotein and increases blood triglycerides.[1]

Medical uses

Ensitrelvir is indicated for the treatment of COVID-19.[1]

History

As of 2022, ensitrelvir had reached Phase III clinical trials.[10] The Japanese government is reportedly considering allowing Shionogi permission to apply for approval for medical use before the final steps of trials are completed, potentially speeding up the release for sale. This conditional early approval system has previously been used in Japan to accelerate the progression to market of other antiviral drugs targeting COVID-19, including remdesivir and molnupiravir.[11] In a study of 428 patients, viral load was reduced, but symptoms were not significantly reduced.[12]

In February 2022, the company sought emergency approval from regulators in Japan.[3][12]

Shionogi announced they had reached a preliminary agreement to supply 1 million doses to the Japanese government once the drug is approved. The CEO said they could have capacity to make 10 million doses a year.[13]

Ensitrelvir may be effective in treating smell and taste loss from COVID-19 infection. In a 2023 study, the drug was associated with a 39% reduction in these symptoms.[14]

Society and culture

Ensitrelvir was approved for emergency use in Japan in November 2022.[1][3][4]

Names

Ensitrelvir is the International Nonproprietary Name.[15]

References
  1. "Xocova (Ensitrelvir Fumaric Acid) Tablets 125mg Approved in Japan for the Treatment of SARS-CoV-2 Infection, under the Emergency Regulatory Approval System". Shionogi (Press release). 22 November 2022. Retrieved 28 November 2022.
  2. McCarthy MW (December 2022). "Ensitrelvir as a potential treatment for COVID-19". Expert Opin Pharmacother. 23 (18): 1995–1998. doi:10.1080/14656566.2022.2146493. PMID 36350029. S2CID 253418404.
  3. Fujikawa M (22 November 2022). "Japan Approves First Homegrown Covid-19 Antiviral Pill". The Wall Street Journal. Retrieved 28 November 2022.
  4. "Shionogi's Covid antiviral lands first approval in Japan's new emergency approval pathway". Endpoints News. 22 November 2022. Retrieved 28 November 2022.
  5. "Xocova: Powerful New Japanese Pill for Coronavirus Treatment". BioPharma Media. February 2022.
  6. Unoh Y, Uehara S, Nakahara K, Nobori H, Yamatsu Y, Yamamoto S, et al. (May 2022). "Discovery of S-217622, a Noncovalent Oral SARS-CoV-2 3CL Protease Inhibitor Clinical Candidate for Treating COVID-19". Journal of Medicinal Chemistry. 65 (9): 6499–6512. doi:10.1021/acs.jmedchem.2c00117. PMC 8982737. PMID 35352927.
  7. "Shionogi presents positive Ph II/III results for COVID-19 antiviral S-217622". thepharmaletter.com. 31 January 2022.
  8. "Shionogi's new COVID pill appears to ease omicron symptoms". Nikkei Asia. 21 December 2021.
  9. Uraki R, Kiso M, Iida S, Imai M, Takashita E, Kuroda M, et al. (IASO study team) (May 2022). "Characterization and antiviral susceptibility of SARS-CoV-2 Omicron/BA.2". Nature. 607 (7917): 119–127. Bibcode:2022Natur.607..119U. doi:10.1038/s41586-022-04856-1. PMC 10579982. PMID 35576972. S2CID 248833104.
  10. Tyndall JD (May 2022). "S-217622, a 3CL Protease Inhibitor and Clinical Candidate for SARS-CoV-2". Journal of Medicinal Chemistry. 65 (9): 6496–6498. doi:10.1021/acs.jmedchem.2c00624. PMID 35507419. S2CID 248513467.
  11. "Japan to consider early approval for Shionogi COVID-19 pill". Japan Times. 8 February 2022.
  12. "Japan's Shionogi seeks approval for COVID-19 pill". Reuters. 25 February 2022.
  13. "Japan's Shionogi signs government supply pact for pill to fight COVID". Reuters. 25 March 2022.
  14. Lenharo, Mariana (17 October 2023). "New pill helps COVID smell and taste loss fade quickly". Nature. doi:10.1038/d41586-023-03244-7. PMID 37853192. S2CID 264303912. {{cite journal}}: Check |s2cid= value (help)
  15. World Health Organization (2022). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 88". WHO Drug Information. 36 (3): 89. hdl:10665/363551.
  • "Ensitrelvir". Drug Information Portal. U.S. National Library of Medicine.
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