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Nirmatrelvir

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15 API Suppliers, 4 USDMF, 3 KDMF, 4 NDC API, 12 Listed Suppliers, $ API Reference Price

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3 KDMF
4 NDC API
12 Listed Suppliers
$ API Reference Price

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12 Intermediates Suppliers

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5 FDF Dossiers, 1 Europe, 2 Canada, 1 South Africa, 1 Listed Dossiers

5 FDF Dossiers
1 Europe
2 Canada
1 South Africa
1 Listed Dossiers

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Chemistry

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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 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 Formula	C₂₃H₃₂F₃N₅O₄
Molecular Weight	499.5 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	499.24063901 g/mol
Monoisotopic Mass	499.24063901 g/mol
Topological Polar Surface Area	131 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	964
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 T_max of nirmatrelvir, when given with ritonavir, is 3 hours. After a single oral dose of 300mg nirmatrelvir and 100mg ritonavir in healthy subjects, the C_max and AUC_inf 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 (3CL^PRO) of SARS-CoV-2. This cysteine is responsible to the activity of the 3CL^PRO of SARS-CoV-2 and potentially other members of the coronavirus family. The 3CL^PRO, also known as the main protease or non structural protein 5, is responsible for cleaving polyproteins 1a and 1ab. These polyproteins contain the 3CL^PRO itself, a papain-like (PL) cysteine protease, and 14 other nonstructural proteins. Without the activity of the 3CL^PRO, nonstructural proteins (including proteases) cannot be released to perform their functions, inhibiting viral replication.

API SUPPLIERS

01

Biophore India Pharmaceuticals Pvt...

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI India 2024

Booth #1.A01

Biophore is a research-driven global pharmaceutical company focused on niche APIs for the generic industry.

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India

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USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

02

Metrochem API Private Limited

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI India 2024

Booth #3.D07

Metrochem has been delivering customized volume & quality products to customers across the world, taking utmost care of their needs.

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India

Virtual Booth

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USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

03

Gonane Pharma

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI India 2024

Booth #2.A34

Gonane has API manufacturing expertise in new-age Corticosteroids, Hormones and other pharma raw materials.

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India

Virtual Booth

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04

Century Pharmaceuticals

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI India 2024

Booth #2.F34

Century has been an API manufacturer for over 30 years & is the partner of choice for multipurpose custom manufacturing projects.

Contact Supplier

India

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

05

HRV Global Life Sciences

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI India 2024

Booth #2.D38

HRV Global Life Sciences - Market Expansion Leader in Pharmaceuticals.

Contact Supplier

India

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USDMF CEP/COS JDMF EU-WC NDC KDMF VMF AU

AUDIT

06

Optimus Pharma

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

Not Confirmed

07

Cipla

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

Not Confirmed

08

MSN Laboratories

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

Not Confirmed

09

HONOUR LAB LTD

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

Not Confirmed

10

Synaptics Labs

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

Not Confirmed

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