Back نيرماترلفير Arabic পিএফ-০৭৩২১৩৩২ Bengali/Bangla Nirmatrelvir Catalan Nirmatrelvir Czech Nirmatrelvir German Νιρματρελβίρη Greek Nirmatrelvir Esperanto Nirmatrelvir French Nirmatrelvir Italian ニルマトレルビル Japanese

Nirmatrelvir

Nirmatrelvir
Clinical data
Pronunciation/nɜːrˈmætrəlvɪər/
nur-MAT-rəl-veer or /ˌnɜːrməˈtrɛlvɪər/
NUR-mə-TREL-veer
Other namesPF-07321332
License data
Pregnancy
category
Routes of
administration		By mouth
ATC code
  • None
Legal status
Legal status
Identifiers
  • (1R,2S,5S)-N-[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]-3-[(2S)-3,3-dimethyl-2-[(2,2,2-trifluoroacetyl)amino]butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
Chemical and physical data
FormulaC23H32F3N5O4
Molar mass499.535 g·mol−1
3D model (JSmol)
Melting point192.9 °C (379.2 °F) [3]
  • CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)C(F)(F)F)C(=O)N[C@@H](C[C@@H]3CCNC3=O)C#N)C
  • InChI=1S/C23H32F3N5O4/c1-21(2,3)16(30-20(35)23(24,25)26)19(34)31-10-13-14(22(13,4)5)15(31)18(33)29-12(9-27)8-11-6-7-28-17(11)32/h11-16H,6-8,10H2,1-5H3,(H,28,32)(H,29,33)(H,30,35)/t11-,12-,13-,14-,15-,16+/m0/s1
  • Key:LIENCHBZNNMNKG-OJFNHCPVSA-N
Xray crystal structure PDB:7si9
X-ray crystal structure (PDB:7SI9 and 7VH8) of the SARS-CoV-2 protease inhibitor nirmatrelvir bound to the viral 3CLpro protease enzyme. Ribbon diagram of the protein with the drug shown as sticks. The catalytic residues (His41, Cys145) are shown as yellow sticks.

Nirmatrelvir is an antiviral medication developed by Pfizer which acts as an orally active 3C-like protease inhibitor.[3][4][5][6][7] It is part of a nirmatrelvir/ritonavir combination used to treat COVID-19 and sold under the brand name Paxlovid.[8]

Despite earning billions for Pfizer (e.g. $4.1B in Q1 2022 alone[9][10]), research into the efficacy of nirmatrelvir/ritonavir over placebo has shown mixed results (see Research below).

  1. ^ "Updates to the Prescribing Medicines in Pregnancy database". Therapeutic Goods Administration (TGA). 12 May 2022. Archived from the original on 3 April 2022. Retrieved 13 May 2022.
  2. ^ "Notice: Nirmatrelvir (COVID-19) added to Prescription Drug List (PDL)". Health Canada. 17 January 2022. Archived from the original on 29 May 2022. Retrieved 29 May 2022.
  3. ^ a b Cite error: The named reference Owen was invoked but never defined (see the help page).
  4. ^ Şimşek-Yavuz S, Komsuoğlu Çelikyurt FI (August 2021). "Antiviral treatment of COVID-19: An update". Turkish Journal of Medical Sciences. 51 (SI-1): 3372–3390. doi:10.3906/sag-2106-250. PMC 8771049. PMID 34391321. S2CID 237054672.
  5. ^ Ahmad B, Batool M, Ain QU, Kim MS, Choi S (August 2021). "Exploring the Binding Mechanism of PF-07321332 SARS-CoV-2 Protease Inhibitor through Molecular Dynamics and Binding Free Energy Simulations". International Journal of Molecular Sciences. 22 (17): 9124. doi:10.3390/ijms22179124. PMC 8430524. PMID 34502033.
  6. ^ "Pfizer Announces Additional Phase 2/3 Study Results Confirming Robust Efficacy of Novel COVID-19 Oral Antiviral Treatment Candidate in Reducing Risk of Hospitalization or Death" (Press release). Pfizer. 14 December 2021. Archived from the original on 26 December 2021. Retrieved 25 December 2021 – via Business Wire.
  7. ^ Vandyck K, Deval J (August 2021). "Considerations for the discovery and development of 3-chymotrypsin-like cysteine protease inhibitors targeting SARS-CoV-2 infection". Current Opinion in Virology. 49: 36–40. doi:10.1016/j.coviro.2021.04.006. PMC 8075814. PMID 34029993.
  8. ^ "Paxlovid- nirmatrelvir and ritonavir kit". DailyMed. Archived from the original on 31 December 2021. Retrieved 30 December 2021.
  9. ^ "Pfizer pulls Q1 surprise with $4.1B in sales of COVID products, despite plummeting demand". FiercePharma. Retrieved 8 May 2024.
  10. ^ "Pfizer cuts earnings, revenue guidance as Covid sales slump". CNBC. Retrieved 8 May 2024.

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