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Compound Detail

CHEMBL571987

LERSIVIRINE
🧪 Phase II
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🧪 Phase II
CCc1nn(CCO)c(CC)c1Oc1cc(C#N)cc(C#N)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL571987
Name LERSIVIRINE
Phase Phase II
Structure Type MOL
InChI Key MCPUZZJBAHRIPO-UHFFFAOYSA-N

Known Names

Lersivirina Lersivirine UK-453,061 UK-453061
5
Targets
16
Activities
4
Assay Types
15
PK Parameters
20
Publications
4
Known Names
1
Indications
1
Mechanisms

Molecular Properties

310.4
MW (Da)
2.54
ALogP
6
HBA
1
HBD
94.9
PSA (Ų)
0.88
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -vir-
USAN Year 2008

Extended Properties

Molecular Formula C17H18N4O2
MW 310.36
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -1.07

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase ✓ ✓

Indications

HIV Infections

Activity Summary

IC50 8 meas. best 8.4
EC50 6 meas. best 10.3
Kd 1 meas. best 6.21
Ki 1 meas. best 6.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 10.3 8.934 0.1 5
Human immunodeficiency virus
CHEMBL613758
 IC50 8.4 8.4 4.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 6.93 6.8 118.0 2
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Ki 6.93 6.93 117.0 1
Unchecked
CHEMBL612545
 IC50 6.92 6.4533 119.0 3
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Kd 6.21 6.21 624.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.26 4.26 54670.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 10967.32 ng.hr.mL-1 Homo sapiens
AUC 11167.68 ng.hr.mL-1 Homo sapiens
CL 25.9 mL.min-1.kg-1 Rattus norvegicus
CL 25.9 mL.min-1.kg-1 Rattus norvegicus
Cmax 4910.43 nM Homo sapiens
Cmax 4684.88 nM Homo sapiens
T1/2 1.6 hr Rattus norvegicus
T1/2 1.217 hr Homo sapiens
T1/2 6.223 hr Homo sapiens
T1/2 6.91 hr Homo sapiens
T1/2 1.217 hr Homo sapiens
T1/2 1.6 hr Rattus norvegicus
Tmax 2.0 hr Homo sapiens
Tmax 5.0 hr Homo sapiens
Vd 1.6 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.05 nM 10.3 Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as in... 20660667
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as in... 20660667
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV1 infected in human TZM-bl cells assessed as viral... 25199582
Human immunodeficiency virus 1 EC50 = 3.96 nM 8.4 Antiviral activity against wild type HIV1 NL4-3 infected in human HeLaP4 cells a... 20660667
Human immunodeficiency virus IC50 = 4.0 nM 8.4 Antiviral activity against HIV RF infected in human SupT1 cells 19748778
Human immunodeficiency virus 1 EC50 = 7.05 nM 8.15 Antiviral activity against HIV1 NL4-3 harboring reverse transcriptase K103N muta... 20660667
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 118.0 nM 6.93 Inhibition of HIV1 reverse transcriptase activity by primer extension assay 20660667
Human immunodeficiency virus type 1 reverse transcriptase Ki = 117.0 nM 6.93 Mixed non-competitive inhibition of HIV1 reverse transcriptase activity 20660667
Unchecked IC50 = 119.0 nM 6.92 Inhibition of HIV reverse transcriptase 19748778
Unchecked IC50 = 119.0 nM 6.92 Inhibition of HIV RT 20804202
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 215.0 nM 6.67 Inhibition of HIV1 HXB2 reverse transcriptase K103N mutant activity by primer ex... 20660667
Human immunodeficiency virus type 1 reverse transcriptase Kd = 624.0 nM 6.21 Binding affinity to recombinant HIV1 reverse transcriptase by isothermal calorim... 20660667
Unchecked IC50 = 3000.0 nM 5.52 Inhibition of human phosphodiesterase 4 20660667
Trypanosoma brucei rhodesiense IC50 = 54670.0 nM 4.26 Antitrypanocidal activity against suramin-sensitive Trypanosoma brucei rhodesien... 25199582

Literature References

PubMed DOI Target Context # Activities
20660667 10.1128/aac.01455-09 Human immunodeficiency virus 1 51
20660667 10.1128/aac.01455-09 Unchecked 30
20660667 10.1128/aac.01455-09 Human immunodeficiency virus type 1 reverse transcriptase 20
20160047 10.1128/aac.01110-09 Homo sapiens 16
19748778 10.1016/j.bmcl.2009.08.080 Unchecked 11
22071300 10.1016/j.bmcl.2011.10.027 Human immunodeficiency virus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19748778 10.1016/j.bmcl.2009.08.080 Rattus norvegicus 3
20804202 10.1021/jm100762r Rattus norvegicus 2
19748778 10.1016/j.bmcl.2009.08.080 Human immunodeficiency virus 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
22268494 10.1021/jm200990c Human immunodeficiency virus 1 2
19748778 10.1016/j.bmcl.2009.08.080 Voltage-gated inwardly rectifying potassium channel KCNH2 1
19748778 10.1016/j.bmcl.2009.08.080 Liver microsomes 1
20804202 10.1021/jm100762r Liver microsomes 1
19748778 10.1016/j.bmcl.2009.08.080 ADMET 1
34003642 10.1021/acs.jmedchem.0c02245 Cytochrome P450 3A 1
20660667 10.1128/aac.01455-09 Adrenergic receptor alpha-1 1

Data from ChEMBL 36 via Core Engine