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Wikipedia

Ensitrelvir

April 16, 2024

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.[8][9][10]

Ensitrelvir
Clinical data
Trade namesXocova
Other namesS-217622
Routes of
administration		By mouth
ATC code
Legal status
Legal status
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
  • 2647530-73-0
  • 2757470-18-9
PubChem CID
  • 162533924
UNII
  • PX665RAA3H
KEGG
  • D12353
Chemical and physical data
FormulaC22H17ClF3N9O2
Molar mass531.88 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 in a Japanese blister pack

The most common adverse events include transient decreases in high-density lipoprotein and increases blood triglycerides.[8]

Medical uses edit

Ensitrelvir is indicated for the treatment of COVID-19.[8]

History edit

As of 2022, ensitrelvir had reached Phase III clinical trials.[11] 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.[12] In a study of 428 patients, viral load was reduced, but symptoms were not significantly reduced.[13]

In February 2022, the company sought emergency approval from regulators in Japan.[3][13]

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.[14]

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.[15]

Society and culture edit

Legal status edit

Ensitrelvir was approved for emergency use in Japan in November 2022,[8][3][4] before gaining full approval in March 2024.[1] It was approved in Singapore in November 2023.[16]

In April 2023, ensitrelvir was given a "Fast Track" designation from the US Food and Drug Administration.[17]

Names edit

Ensitrelvir is the International Nonproprietary Name.[18]

Research edit

Ensitrelvir is being studied for its potential use as post-exposure prophylaxis (PEP) after SARS-CoV-2 exposure.[19][20] The SCORPIO-PEP trial is a global Phase 3 trial that will evaluate the safety and efficacy of the drug in preventing symptomatic SARS-CoV-2 infection in household contacts of people who tested positive for COVID-19.[20][21][22]

An April 2024 pre-clinical study in a mouse model investigating ensitrelvir demonstrated its potential use as a pre-exposure prophylactic (PrEP) against developing COVID-19. When administered 24 hours before viral exposure, ensitrelvir significantly increased survival rates, inhibited weight loss, and suppressed viral replication in aged mice.[23]

References edit

  1. ^ a b "Japan health ministry approves Shionogi's COVID drug Xocova". NHK WORLD. 5 March 2024. Retrieved 6 March 2024.
  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. ^ a b c Fujikawa M (22 November 2022). "Japan Approves First Homegrown Covid-19 Antiviral Pill". The Wall Street Journal. Retrieved 28 November 2022.
  4. ^ a b "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. ^ a b c d "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.
  9. ^ "Shionogi's new COVID pill appears to ease omicron symptoms". Nikkei Asia. 21 December 2021.
  10. ^ 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.
  11. ^ 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.
  12. ^ "Japan to consider early approval for Shionogi COVID-19 pill". Japan Times. 8 February 2022.
  13. ^ a b "Japan's Shionogi seeks approval for COVID-19 pill". Reuters. 25 February 2022.
  14. ^ "Japan's Shionogi signs government supply pact for pill to fight COVID". Reuters. 25 March 2022.
  15. ^ Lenharo M (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.
  16. ^ "Shionogi reports data from Phase III portion of Covid-19 drug trial". Clinical Trials Arena. 12 February 2024. Retrieved 6 March 2024.
  17. ^ Ducharme J (25 January 2024). "When Will We Get New COVID-19 Drugs?". Time. Retrieved 6 March 2024.
  18. ^ World Health Organization (2022). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 88". WHO Drug Information. 36 (3): 89. hdl:10665/363551.
  19. ^ Cosdon N (31 March 2023). "Ensitrelvir: A COVID-19 Antiviral That Remains Effective Against New Variants". ContagionLive. Retrieved 28 October 2023.
  20. ^ a b "Shionogi presses on with Xocova research following Japanese approval". The Pharma Letter. 16 February 2023. Retrieved 28 October 2023.
  21. ^ . University of Kansas Medical Center. Archived from the original on 28 October 2023. Retrieved 28 October 2023. SCORPIO-PEP is a 28-day study to assess the prevention of COVID-19 infection in those who have been exposed through household contact.
  22. ^ "Shionogi Enrolls the First Participant in Japan in its Global Phase 3 Trial of Ensitrelvir for the Prevention of Symptomatic SARS-CoV-2 Infection" (Press release). Osaka, Japan. 9 June 2023. Retrieved 28 October 2023.
  23. ^ Nobori H, Baba K, Kuroda T, Baba K, Matsumoto K, Yoshida S, et al. (April 2024). "Prophylactic effect of ensitrelvir in mice infected with SARS-CoV-2". Antiviral Research. 224: 105852. doi:10.1016/j.antiviral.2024.105852. PMID 38428748.

External links edit

  • "Ensitrelvir". Drug Information Portal. U.S. National Library of Medicine.

April 16, 2024
ensitrelvir, sold, under, brand, name, xocova, antiviral, medication, used, treatment, covid, developed, shionogi, partnership, with, hokkaido, university, acts, orally, active, like, protease, inhibitor, taken, mouth, clinical, datatrade, namesxocovaother, na. 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 8 9 10 EnsitrelvirClinical dataTrade namesXocovaOther namesS 217622Routes ofadministrationBy mouthATC codeJ05AE11 WHO Legal statusLegal statusJP Rx only 1 IdentifiersIUPAC name 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 dioneCAS Number2647530 73 02757470 18 9PubChem CID162533924UNIIPX665RAA3HKEGGD12353Chemical and physical dataFormulaC 22H 17Cl F 3N 9O 2Molar mass531 88 g mol 13D model JSmol Interactive imageSMILES Cn1cnc CN2C O N Cc3cc F c F cc3F C N c3cc4cn C nc4cc3Cl NC2 O n1InChI 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 NXocova in a Japanese blister packThe most common adverse events include transient decreases in high density lipoprotein and increases blood triglycerides 8 Contents 1 Medical uses 2 History 3 Society and culture 3 1 Legal status 3 2 Names 4 Research 5 References 6 External linksMedical uses editEnsitrelvir is indicated for the treatment of COVID 19 8 History editAs of 2022 update ensitrelvir had reached Phase III clinical trials 11 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 12 In a study of 428 patients viral load was reduced but symptoms were not significantly reduced 13 In February 2022 the company sought emergency approval from regulators in Japan 3 13 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 14 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 15 Society and culture editLegal status edit Ensitrelvir was approved for emergency use in Japan in November 2022 8 3 4 before gaining full approval in March 2024 1 It was approved in Singapore in November 2023 16 In April 2023 ensitrelvir was given a Fast Track designation from the US Food and Drug Administration 17 Names edit Ensitrelvir is the International Nonproprietary Name 18 Research editEnsitrelvir is being studied for its potential use as post exposure prophylaxis PEP after SARS CoV 2 exposure 19 20 The SCORPIO PEP trial is a global Phase 3 trial that will evaluate the safety and efficacy of the drug in preventing symptomatic SARS CoV 2 infection in household contacts of people who tested positive for COVID 19 20 21 22 An April 2024 pre clinical study in a mouse model investigating ensitrelvir demonstrated its potential use as a pre exposure prophylactic PrEP against developing COVID 19 When administered 24 hours before viral exposure ensitrelvir significantly increased survival rates inhibited weight loss and suppressed viral replication in aged mice 23 References edit a b Japan health ministry approves Shionogi s COVID drug Xocova NHK WORLD 5 March 2024 Retrieved 6 March 2024 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 a b c Fujikawa M 22 November 2022 Japan Approves First Homegrown Covid 19 Antiviral Pill The Wall Street Journal Retrieved 28 November 2022 a b Shionogi s Covid antiviral lands first approval in Japan s new emergency approval pathway Endpoints News 22 November 2022 Retrieved 28 November 2022 Xocova Powerful New Japanese Pill for Coronavirus Treatment BioPharma Media February 2022 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 Shionogi presents positive Ph II III results for COVID 19 antiviral S 217622 thepharmaletter com 31 January 2022 a b c d 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 Shionogi s new COVID pill appears to ease omicron symptoms Nikkei Asia 21 December 2021 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 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 Japan to consider early approval for Shionogi COVID 19 pill Japan Times 8 February 2022 a b Japan s Shionogi seeks approval for COVID 19 pill Reuters 25 February 2022 Japan s Shionogi signs government supply pact for pill to fight COVID Reuters 25 March 2022 Lenharo M 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 Shionogi reports data from Phase III portion of Covid 19 drug trial Clinical Trials Arena 12 February 2024 Retrieved 6 March 2024 Ducharme J 25 January 2024 When Will We Get New COVID 19 Drugs Time Retrieved 6 March 2024 World Health Organization 2022 International nonproprietary names for pharmaceutical substances INN recommended INN list 88 WHO Drug Information 36 3 89 hdl 10665 363551 Cosdon N 31 March 2023 Ensitrelvir A COVID 19 Antiviral That Remains Effective Against New Variants ContagionLive Retrieved 28 October 2023 a b Shionogi presses on with Xocova research following Japanese approval The Pharma Letter 16 February 2023 Retrieved 28 October 2023 Studies Currently Enrolling University of Kansas Medical Center Archived from the original on 28 October 2023 Retrieved 28 October 2023 SCORPIO PEP is a 28 day study to assess the prevention of COVID 19 infection in those who have been exposed through household contact Shionogi Enrolls the First Participant in Japan in its Global Phase 3 Trial of Ensitrelvir for the Prevention of Symptomatic SARS CoV 2 Infection Press release Osaka Japan 9 June 2023 Retrieved 28 October 2023 Nobori H Baba K Kuroda T Baba K Matsumoto K Yoshida S et al April 2024 Prophylactic effect of ensitrelvir in mice infected with SARS CoV 2 Antiviral Research 224 105852 doi 10 1016 j antiviral 2024 105852 PMID 38428748 External links edit Ensitrelvir Drug Information Portal U S National Library of Medicine Portals nbsp Medicine nbsp Viruses nbsp COVID 19 Retrieved from https en wikipedia org w index php title Ensitrelvir amp oldid 1217832183, wikipedia, wiki, book, books, library,

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