Nirmatrelvir information

Nirmatrelvir
Clinical data
Pronunciation	/nɜːrˈmætrəlvɪər/; nur-MAT-rəl-veer or /ˌnɜːrməˈtrɛlvɪər/; NUR-mə-TREL-veer
Other names	PF-07321332
License data	US DailyMed: Nirmatrelvir;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
ATC code	None;
Legal status
Legal status	CA: ℞-only;
Identifiers
	IUPAC name (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	2628280-40-8;
PubChem CID	155903259;
DrugBank	DB16691;
ChemSpider	114826566;
UNII	7R9A5P7H32;
KEGG	D12244;
ChEBI	CHEBI:170007;
Chemical and physical data
Formula	C23H32F3N5O4
Molar mass	499.535 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	192.9 °C (379.2 °F)
	SMILES 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 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;

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).

^ "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.
^ "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.
^ ^a ^b Cite error: The named reference Owen was invoked but never defined (see the help page).
^ 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.
^ 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.
^ "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.
^ 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.
^ "Paxlovid- nirmatrelvir and ritonavir kit". DailyMed. Archived from the original on 31 December 2021. Retrieved 30 December 2021.
^ "Pfizer pulls Q1 surprise with $4.1B in sales of COVID products, despite plummeting demand". FiercePharma. Retrieved 8 May 2024.
^ "Pfizer cuts earnings, revenue guidance as Covid sales slump". CNBC. Retrieved 8 May 2024.

[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.

[Owen-3] 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.

[pfizer2-6] "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.

[:0-7] 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.

[Paxlovid_FDA_label-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.

Nirmatrelvir information

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Clinical data

Pronunciation	/nɜːrˈmætrəlvɪər/ nur-MAT-rəl-veer or /ˌnɜːrməˈtrɛlvɪər/ NUR-mə-TREL-veer
Other names	PF-07321332
License data	US DailyMed: Nirmatrelvir
Pregnancy category	AU: B3^[1]
Routes of administration	By mouth
ATC code	None
Legal status
Legal status	CA: ℞-only^[2]
Identifiers
IUPAC name (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	2628280-40-8
PubChem CID	155903259
DrugBank	DB16691
ChemSpider	114826566
UNII	7R9A5P7H32
KEGG	D12244
ChEBI	CHEBI:170007
Chemical and physical data
Formula	C₂₃H₃₂F₃N₅O₄
Molar mass	499.535 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	192.9 °C (379.2 °F) ^[3]
SMILES 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 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