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Also known as: 2628280-40-8, 7r9a5p7h32, Paxlovid, Pf-07321332, Pf07321332, Nirmatrelvir [usan]
Molecular Formula
C23H32F3N5O4
Molecular Weight
499.5  g/mol
InChI Key
LIENCHBZNNMNKG-OJFNHCPVSA-N
FDA UNII
7R9A5P7H32

Nirmatrelvir
Nirmatrelvir is an orally bioavailable, peptidomimetic inhibitor of the severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) main protease (Mpro; 3C-like protease; 3CL protease; 3CLpro; nsp5 protease), with potential antiviral activity against SARS-CoV-2 and other coronaviruses. Upon oral administration, nirmatrelvir selectively targets, binds to, and inhibits the activity of SARS-CoV-2 Mpro. This inhibits the proteolytic cleavage of viral polyproteins, thereby inhibiting the formation of viral proteins including helicase, single-stranded-RNA-binding protein, RNA-dependent RNA polymerase, 20-O-ribose methyltransferase, endoribonuclease and exoribonuclease. This prevents viral transcription and replication.
1 2D Structure

Nirmatrelvir

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 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
2.1.3 InChI Key
LIENCHBZNNMNKG-OJFNHCPVSA-N
2.1.4 Canonical SMILES
CC1(C2C1C(N(C2)C(=O)C(C(C)(C)C)NC(=O)C(F)(F)F)C(=O)NC(CC3CCNC3=O)C#N)C
2.1.5 Isomeric 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
2.2 Other Identifiers
2.2.1 UNII
7R9A5P7H32
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (1r,2s,5s)-n-((1s)-1-cyano-2-((3s)-2-oxopyrrolidin-3-yl)ethyl)-6,6-dimethyl-3-(3-methyl-n-(trifluoroacetyl)-l-valyl)-3-azabicyclo(3.1.0)hexane-2-carboxamide

2. Pf-07321332

3. Pf07321332

2.3.2 Depositor-Supplied Synonyms

1. 2628280-40-8

2. 7r9a5p7h32

3. Paxlovid

4. Pf-07321332

5. Pf07321332

6. Nirmatrelvir [usan]

7. (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

8. (1r,2s,5s)-n-((1s)-1-cyano-2-((3s)-2-oxopyrrolidin-3-yl)ethyl)-6,6-dimethyl-3-(3-methyl-n-(trifluoroacetyl)-l-valyl)-3-azabicyclo(3.1.0)hexane-2-carboxamide

9. (1r,2s,5s)-n-[(1s)-1-cyano-2-[(3s)-2-oxopyrrolidin-3-yl]ethyl]-3-[(2s)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

10. (1r,2s,5s)-n-{(1s)-1-cyano-2-[(3s)-2-oxopyrrolidin-3-yl]ethyl}-3-[(2s)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

11. (1r,2s,5s)-n-{(1s)-1-cyano-2-[(3s)-2-oxopyrrolidin-3-yl]ethyl}-6,6-dimethyl-3-[3-methyl-n-(trifluoroacetyl)-l-valyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide

12. 3-azabicyclo(3.1.0)hexane-2-carboxamide, N-((1s)-1-cyano-2-((3s)-2-oxo-3-pyrrolidinyl)ethyl)-3-((2s)-3,3-dimethyl-1-oxo-2-((2,2,2-trifluoroacetyl)amino)butyl)-6,6-dimethyl-, (1r,2s,5s)-

13. 3-azabicyclo[3.1.0]hexane-2-carboxamide, N-[(1s)-1-cyano-2-[(3s)-2-oxo-3-pyrrolidinyl]ethyl]-3-[(2s)-3,3-dimethyl-1-oxo-2-[(2,2,2-trifluoroacetyl)amino]butyl]-6,6-dimethyl-, (1r,2s,5s)-

14. Science.abl4784, 6

15. Nirmatrelvir [inn]

16. Nirmatrelvir [jan]

17. Nirmatrelvir [who-dd]

18. Unii-7r9a5p7h32

19. Pf07321332(nirmatrelvir)

20. Chembl4802135

21. Gtpl11503

22. Chebi:170007

23. Bdbm496902

24. Dtxsid501336829

25. Ex-a5024

26. Paxlovid (nirmatrelvir + Ritonavir)

27. Who 12161

28. At31194

29. Ac-35259

30. Example E61 [wo2021250648a1]

31. Paxlovid Component Pf-07321332

32. Hy-138687

33. 870124 More Info Pf-00835231

34. Cs-0166635

35. Pf 07321332

36. (1r,2s,5s)-n-((s)-1-cyano-2-((s)-2-oxopyrrolidin-3-yl)ethyl)-3-((s)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

37. (1s,3as,4ar)-n-[(1s)-1-cyano-2-[(3s)-2-oxotetrahydro-1h-pyrrol-3-yl]ethyl]-2-[(2s)-3,3-dimethyl-1-oxo-2-[(trifluoroacetyl)amino]butyl]-4,4-dimethyl-2,3,3a,4a-tetrahydro-1h-cyclopropa[1,2-c]pyrrole-1-carboxamide

2.4 Create Date
2021-05-01
3 Chemical and Physical Properties
Molecular Weight 499.5 g/mol
Molecular Formula C23H32F3N5O4
XLogP32.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass499.24063901 g/mol
Monoisotopic Mass499.24063901 g/mol
Topological Polar Surface Area131 Ų
Heavy Atom Count35
Formal Charge0
Complexity964
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Nirmatrelvir has received FDA emergency use authorization, in combination with [ritonavir], for the treatment of mild-to-moderate coronavirus disease 2019 (COVID-19) in adults and pediatric patients (12 years of age and older weighing at least 40 kg) with positive results of direct severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) viral testing, and who are at high risk for progression to severe COVID-19, including hospitalization or death.


Paxlovid is indicated for the treatment of coronavirus disease 2019 (COVID-19) in adults who do not require supplemental oxygen and who are at increased risk for progressing to severe COVID 19 (see section 5. 1).


5 Pharmacology and Biochemistry
5.1 Pharmacology

Nirmatrelvir is administered alongside ritonavir, a potent inhibitor of CYP3A enzymes, in order to inhibit its metabolism and increase plasma nirmatrelvir concentrations. While therapeutically beneficial, the use of ritonavir poses a significant risk of drug interaction due to its potent inhibition profile - patients and clinicians should consult the prescribing information for Paxlovid (nirmatrelvir and ritonavir) to evaluate any potential for drug interaction with existing medications prior to the initiation of Paxlovid.


5.2 MeSH Pharmacological Classification

Viral Protease Inhibitors

Compounds that specifically inhibit PROTEOLYTIC ENZYMES that are encoded by VIRUSES. (See all compounds classified as Viral Protease Inhibitors.)


5.3 ATC Code

Not yet assigned


5.4 Absorption, Distribution and Excretion

Absorption

The median Tmax of nirmatrelvir, when given with ritonavir, is 3 hours. After a single oral dose of 300mg nirmatrelvir and 100mg ritonavir in healthy subjects, the Cmax and AUCinf of nirmatrelvir were 2.21 g/mL and 23.01 g*hr/mL, respectively.


Route of Elimination

The major route of nirmaltrevir elimination is via renal elimination, due in part to its coadministration with ritonavir which inhibits its metabolism. Following oral administration alongside ritonavir, approximately 49.6% of drug-related material was recovered in the feces and 35.3% was recovered in the urine.


Volume of Distribution

The mean volume of distribution of nirmatrelvir, when given with ritonavir, is 104.7 liters.


Clearance

The mean oral clearance of nirmatrelvir, administered with ritonavir, is 8.99 L/h.


5.5 Metabolism/Metabolites

Nirmatrelvir is a substrate of CYP3A4, but undergoes minimal metabolism when administered alongside ritonavir.


5.6 Biological Half-Life

The mean half-life of nirmatrelvir, administered alongside ritonavir, is 6.05 hours.


5.7 Mechanism of Action

Nirmatrelvir is an inhibitor of a cysteine residue in the 3C-like protease (3CLPRO) of SARS-CoV-2. This cysteine is responsible to the activity of the 3CLPRO of SARS-CoV-2 and potentially other members of the coronavirus family. The 3CLPRO, also known as the main protease or non structural protein 5, is responsible for cleaving polyproteins 1a and 1ab. These polyproteins contain the 3CLPRO itself, a papain-like (PL) cysteine protease, and 14 other nonstructural proteins. Without the activity of the 3CLPRO, nonstructural proteins (including proteases) cannot be released to perform their functions, inhibiting viral replication.


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