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Compound Detail

CHEMBL4802135

NIRMATRELVIR
💊 Approved Drug
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💊 Approved Drug
CC(C)(C)[C@H](NC(=O)C(F)(F)F)C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)N[C@H](C#N)C[C@@H]1CCNC1=O)C2(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4802135
Name NIRMATRELVIR
Phase Approved
Structure Type MOL
InChI Key LIENCHBZNNMNKG-OJFNHCPVSA-N

Known Names

Nirmatrelvir Nirmatrelvir component of paxlovid Pf-07321332 PF07321332
13
Targets
183
Activities
4
Assay Types
30
PK Parameters
20
Publications
4
Known Names
8
Indications
1
Mechanisms

Molecular Properties

499.5
MW (Da)
1.10
ALogP
5
HBA
3
HBD
131.4
PSA (Ų)
0.50
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2023
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

First in Class
USAN Stem -vir
USAN Year 2021

Extended Properties

Molecular Formula C23H32F3N5O4
MW 499.53
Aromatic Rings 0
Heavy Atoms 35
NP-Likeness 0.33

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
SARS coronavirus 3C-like proteinase inhibitor INHIBITOR Replicase polyprotein 1a ✓ ✓

Indications

Influenza, Human Pneumonia Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Post-Acute COVID-19 Syndrome COVID-19 Kidney Diseases Liver Diseases

Activity Summary

EC50 98 meas. best 8.37
IC50 51 meas. best 9.1
Ki 32 meas. best 9.59
Kd 2 meas. best 6.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Replicase polyprotein 1ab
CHEMBL4523582
 Ki 9.59 8.5542 0.3 24
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 9.1 7.4826 0.8 31
Unchecked
CHEMBL612545
 Ki 8.99 7.5013 1.0 8
SARS-CoV-2
CHEMBL4303835
 EC50 8.37 6.477 4.3 82
Unchecked
CHEMBL612545
 IC50 8.0 7.49 10.1 12
Replicase polyprotein 1a
CHEMBL3927
 IC50 7.7 7.7 20.0 1
Middle East respiratory syndrome-related coronavirus
CHEMBL4296578
 EC50 7.61 7.195 24.3 2
Unchecked
CHEMBL612545
 EC50 7.4 7.0633 39.8 3
Human coronavirus OC43
CHEMBL5209665
 EC50 7.16 6.9425 70.0 4
SARS-CoV
CHEMBL4303836
 EC50 7.15 6.985 70.2 2
Human coronavirus 229E
CHEMBL613837
 EC50 7.0 6.7225 100.0 4
Replicase polyprotein 1ab
CHEMBL4523582
 Kd 6.89 6.805 130.0 2
Replicase polyprotein 1ab
CHEMBL4888440
 IC50 6.84 6.84 145.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 6.8 6.415 160.0 2
Cathepsin K
CHEMBL268
 IC50 5.92 5.92 1200.0 1
Cathepsin S
CHEMBL2954
 IC50 5.75 5.75 1800.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 EC50 5.47 5.47 3400.0 1
Cathepsin L2
CHEMBL3272
 IC50 4.84 4.84 14600.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.33 4.33 46400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2308.32 ng.hr.mL-1 Mus musculus
AUC 3336.46 ng.hr.mL-1 Mus musculus
AUC 2311.94 ng.hr.mL-1 Mus musculus
AUC 3361.32 ng.hr.mL-1 Mus musculus
AUC 3.58 uM.hr Mus musculus
AUC 2.38 uM.hr Rattus norvegicus
AUC 2170.0 ng.hr.mL-1 Rattus norvegicus
AUC 18000.0 ng.hr.mL-1 Rattus norvegicus
AUC 3190.0 ng.hr.mL-1 Rattus norvegicus
AUC 68300.0 ng.hr.mL-1 Rattus norvegicus
AUC 746500.0 ng.hr.mL-1 Rattus norvegicus
AUC 1029.0 ng.hr.mL-1 Mus musculus
AUC 1023.0 ng.hr.mL-1 Mus musculus
AUC 2241.0 ng.hr.mL-1 Mus musculus
AUC 2240.0 ng.hr.mL-1 Mus musculus
CL 45.83 mL.min-1.kg-1 Homo sapiens
CL 1175.45 mL.min-1.kg-1 Mus musculus
CL 50.06 mL.min-1.kg-1 Mus musculus
CL 329.0 mL.min-1.kg-1 Mus musculus
CL 17.3 mL.min-1.kg-1 Rattus norvegicus
CL 29.0 mL.min-1.kg-1 Homo sapiens
CL 169.0 mL.min-1.kg-1 Mus musculus
CL 29.9 mL.min-1.kg-1 Rattus norvegicus
CL 17.8 mL.min-1.kg-1 Homo sapiens
CL 30.2 mL.min-1.kg-1 Mus musculus
CL 42.0 mL.min-1.kg-1 Rattus norvegicus
CL 21.8 mL.min-1.g-1 Homo sapiens
CL 35.8 mL.min-1.kg-1 Mus musculus
CL 1.92 mL.min-1.kg-1 Canis lupus familiaris
CL 35.8 mL.min-1.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Replicase polyprotein 1ab Ki = 0.26 nM 9.59 Inhibition of N-terminal hexa-histidine tagged SARS-CoV-2 main protease expresse... 38335815
Replicase polyprotein 1ab IC50 = 0.79 nM 9.1 Inhibition of recombinant full length SARS-CoV-2 3CLpro expressed in Escherichia... 36229406
Unchecked Ki = 1.02 nM 8.99 Inhibition of MERS-CoV main protease using Boc-Abu-Tle-Leu-Gln-AMC as substrate ... 38753594
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Binding affinity to SARS-Cov-2 main protease assessed as inhibition constant 37633203
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Inhibition of recombinant SARS CoV-2 Wuhan-Hu-1 main protease extracted from Esc... 37944867
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Binding affinity to C-terminal His6-tagged recombinant SARS-CoV-2 MPro assessed ... 37244162
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Inhibition of SARS-CoV-2 MPro using Dabcyl-KTSAVLQSGFRKME-Edans as substrate ass... 36549112
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Inhibition of SARS-CoV-2 MPro 37859715
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Binding affinity to SARS-CoV-2 Main protease assessed as inhibition constant 36169610
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Inhibition of SARS-CoV-2 main protease expressed in Escherichia coli using Dabcy... 36475694
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Inhibition of SARS CoV-2 main protease 35688005
Unchecked Ki = 3.0 nM 8.52 Inhibition of full length SARS-CoV-2 3CL protease using Dabcyl-KTSAVLQ-SGFRKME-E... 35291756
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 Inhibition of SARS-CoV-2 Main protease using Dabcyl-KTSAVLQSGFRKME-Edans as subs... 37517202
Replicase polyprotein 1ab Ki = 3.0 nM 8.52 SARS-CoV-2 Coronavirus 3C Protease FRET Assay: The proteolytic activity of the m... -
Replicase polyprotein 1ab Ki = 3.1 nM 8.51 Inhibition of recombinant SARS-CoV-2 Wuhan-Hu-1 main protease expressed in Esche... 38365209
Replicase polyprotein 1ab Ki = 3.11 nM 8.51 Inhibition of SARS-CoV-2 3CL protease assessed as inhibition constant 36760740
Replicase polyprotein 1ab Ki = 3.11 nM 8.51 Binding affinity to SARS-CoV-2 MPro assessed as inhibition constant 36857133
Replicase polyprotein 1ab Ki = 3.11 nM 8.51 Inhibition of SARS-CoV-2 Main protease using peptide substrate assessed as fluor... 38048696
Replicase polyprotein 1ab Ki = 3.11 nM 8.51 Inhibition of SARS-Cov-2 MPro assessed as inhibition constant by FRET assay 38687966
Replicase polyprotein 1ab Ki = 3.11 nM 8.51 Inhibition of SARS CoV-2 MPro 39146284

Literature References

PubMed DOI Target Context # Activities
38335279 10.1021/acs.jmedchem.3c01938 ADMET 49
38432056 10.1016/j.ejmech.2024.116263 SARS-CoV-2 32
35182772 10.1016/j.bmcl.2022.128629 Unchecked 24
37182612 10.1016/j.bmcl.2023.129324 ADMET 21
38687966 10.1021/acs.jmedchem.3c02469 ADMET 21
37756225 10.1021/acs.jmedchem.3c00777 ADMET 20
37187077 10.1016/j.bmc.2023.117316 ADMET 19
37253309 10.1016/j.ejmech.2023.115512 ADMET 11
38335815 10.1016/j.ejmech.2024.116132 SARS-CoV-2 10
36229406 10.1021/acs.jmedchem.2c01081 SARS-CoV-2 7
38335279 10.1021/acs.jmedchem.3c01938 SARS-CoV-2 7
37992202 10.1021/acs.jmedchem.3c01876 SARS-CoV-2 6
37756225 10.1021/acs.jmedchem.3c00777 SARS-CoV-2 5
38518735 10.1016/j.bmc.2023.117577 Unchecked 5
35182772 10.1016/j.bmcl.2022.128629 Replicase polyprotein 1ab 5
37187077 10.1016/j.bmc.2023.117316 Replicase polyprotein 1ab 5
37229831 10.1016/j.ejmech.2023.115503 SARS-CoV-2 5
36857133 10.1021/acs.jmedchem.2c01229 SARS-CoV-2 4
38753594 10.1021/acs.jmedchem.4c00053 SARS-CoV-2 4
39146284 10.1021/acs.jmedchem.4c00535 Replicase polyprotein 1ab 4

Data from ChEMBL 36 via Core Engine