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Compound Detail

CHEMBL3301620

TEMSAVIR
🧪 Phase II
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🧪 Phase II
COc1cnc(-n2cnc(C)n2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12

Basic Information

ChEMBL ID CHEMBL3301620
Name TEMSAVIR
Phase Phase II
Structure Type MOL
InChI Key QRPZBKAMSFHVRW-UHFFFAOYSA-N

Known Names

BMS-626529 Temsavir
11
Targets
63
Activities
3
Assay Types
23
PK Parameters
20
Publications
2
Known Names
1
Indications

Molecular Properties

473.5
MW (Da)
1.63
ALogP
8
HBA
1
HBD
126.3
PSA (Ų)
0.34
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -vir
USAN Year 2014

Extended Properties

Molecular Formula C24H23N7O4
MW 473.49
Aromatic Rings 4
Heavy Atoms 35
NP-Likeness -0.99

Indications

HIV Infections

Activity Summary

IC50 34 meas. best 8.34
EC50 27 meas. best 10.0
Kd 2 meas. best 9.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 10.0 8.9441 0.1 27
Envelope glycoprotein gp160
CHEMBL1293311
Kd 9.08 9.08 0.8 1
Unchecked
CHEMBL612545
Kd 9.08 9.08 0.8 1
Human immunodeficiency virus 1
CHEMBL378
IC50 8.34 6.5978 4.6 23
Unchecked
CHEMBL612545
IC50 7.85 7.85 14.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 4.66 4.66 21900.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 4.6 4.6 25000.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 4.6 4.6 25000.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 4.6 4.6 25000.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 4.6 4.6 25000.0 2
Cytochrome P450 2C19
CHEMBL3622
IC50 4.6 4.6 25000.0 1
Cytochrome P450 2C8
CHEMBL3721
IC50 4.6 4.6 25000.0 1
Cytochrome P450 2B6
CHEMBL4729
IC50 4.6 4.6 25000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 24621.48 ng.hr.mL-1 Rattus norvegicus
AUC 52557.39 ng.hr.mL-1 Rattus norvegicus
AUC 28882.89 ng.hr.mL-1 Canis lupus familiaris
AUC 6628.86 ng.hr.mL-1 Macaca fascicularis
CL 10.0 mL.min-1.g-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Rattus norvegicus
CL 2.6 mL.min-1.kg-1 Canis lupus familiaris
CL 7.5 mL.min-1.kg-1 Macaca fascicularis
CL 5.19 mL.min-1.g-1 Homo sapiens
Cmax 6400.0 nM Rattus norvegicus
F 52.0 % Rattus norvegicus
F 80.0 % Macaca fascicularis
F 80.0 % Canis lupus familiaris
F 80.0 % Rattus norvegicus
F 82.0 % Rattus norvegicus
F 89.0 % Canis lupus familiaris
F 64.0 % Macaca fascicularis
Fu 0.185 - Homo sapiens
Fu 0.131 - Homo sapiens
T1/2 5.9 hr Rattus norvegicus
T1/2 7.633 hr Human immunodeficiency virus 1
T1/2 4.3 hr Rattus norvegicus
T1/2 7.633 hr Human immunodeficiency virus 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.1 nM 10.0 Antiviral activity against HIV-1 subtype F by p24 ELISA 29271653
Human immunodeficiency virus 1 EC50 = 0.1 nM 10.0 Antiviral activity against ENV pseudotyped CCR5-tropic HIV1 JFRL infected in hum... 29920093
Human immunodeficiency virus 1 EC50 = 0.1 nM 10.0 Antiviral activity against ENV pseudotyped HIV1 JFRL infected in human HeLa67 ce... 30940396
Human immunodeficiency virus 1 EC50 = 0.1 nM 10.0 Antiviral activity against HIV-1 expressing JRFL envelope infected in human HeLa... 26584882
Human immunodeficiency virus 1 EC50 = 0.14 nM 9.85 Antiviral activity against HIV 1 isolate JRFL by single cycle infectivity assay 29271653
Human immunodeficiency virus 1 EC50 = 0.14 nM 9.85 Antiviral activity against HIV-1 3B infected in human MT4 cells assessed as redu... 38781921
Human immunodeficiency virus 1 EC50 = 0.34 nM 9.47 Antiviral activity against HIV-1 subtype B by p24 ELISA 29271653
Human immunodeficiency virus 1 EC50 = 0.4 nM 9.4 Antiviral activity against CCR5-tropic HIV1 JRFL infected in human PM1 cells by ... 26116177
Human immunodeficiency virus 1 EC50 = 0.4 nM 9.4 Antiviral activity against HIV-1 JR-FL infected in human PM1 cells harboring CCR... 29271653
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against HIV-1 SF-162 infected in human PM1 cells harboring CC... 29271653
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against CCR5-tropic HIV1 SF162 infected in human PM1 cells by... 26116177
Human immunodeficiency virus 1 EC50 = 0.7 nM 9.15 Antiviral activity against CXCR4-tropic HIV1 LAI infected in human MT2 cells by ... 26116177
Human immunodeficiency virus 1 EC50 = 0.7 nM 9.15 Antiviral activity against HIV-1 LAI infected in human MT2 cells harboring CXCR4... 29271653
Envelope glycoprotein gp160 Kd = 0.83 nM 9.08 Inhibition of [3H]BMS-488043 binding to HIV-1 JRFL gp120 after 1 hr by scintilla... 29920093
Unchecked Kd = 0.83 nM 9.08 Inhibition of [3H]BMS-488043 binding to HIV-1 isolate JRFL gp120 after 60 mins b... 29271653
Human immunodeficiency virus 1 EC50 = 1.14 nM 8.94 Antiviral activity against HIV-1 subtype C by p24 ELISA 29271653
Human immunodeficiency virus 1 EC50 = 1.7 nM 8.77 Antiviral activity against HIV-1 Bal infected in human PM1 cells harboring CCR5 ... 29271653
Human immunodeficiency virus 1 EC50 = 1.7 nM 8.77 Antiviral activity against CCR5-tropic HIV1 BAL infected in human PM1 cells by m... 26116177
Human immunodeficiency virus 1 EC50 = 1.77 nM 8.75 Antiviral activity against HIV-1 isolate CRF02_AG by p24 ELISA 29271653
Human immunodeficiency virus 1 EC50 = 2.2 nM 8.66 Antiviral activity against CXCR4-tropic HIV1 NL4-3 infected in human MT2 cells b... 26116177

Literature References

PubMed DOI Target Context # Activities
29860061 10.1016/j.ejmech.2018.04.062 Human immunodeficiency virus 1 28
29271653 10.1021/acs.jmedchem.7b01337 Human immunodeficiency virus 1 18
29860061 10.1016/j.ejmech.2018.04.062 ADMET 9
26116177 10.1016/j.bmc.2015.06.016 Human immunodeficiency virus 1 7
29920093 10.1021/acs.jmedchem.8b00759 ADMET 7
29920093 10.1021/acs.jmedchem.8b00759 Rattus norvegicus 6
29920093 10.1021/acs.jmedchem.8b00759 Human immunodeficiency virus 1 5
29271653 10.1021/acs.jmedchem.7b01337 Unchecked 5
29920093 10.1021/acs.jmedchem.8b00759 Canis familiaris 4
29920093 10.1021/acs.jmedchem.8b00759 Cynomolgus monkey 4
26584882 10.1016/j.bmcl.2015.11.009 Rattus norvegicus 3
29920093 10.1021/acs.jmedchem.8b00759 No relevant target 3
28266845 10.1021/acs.jmedchem.7b00179 ADMET 3
32031803 10.1021/acs.jmedchem.9b02149 Human immunodeficiency virus 1 3
31285097 10.1016/j.bmc.2019.06.044 Human immunodeficiency virus 1 3
29271653 10.1021/acs.jmedchem.7b01337 No relevant target 2
28266845 10.1021/acs.jmedchem.7b00179 Liver 2
26584882 10.1016/j.bmcl.2015.11.009 Liver microsome 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
29860061 10.1016/j.ejmech.2018.04.062 No relevant target 2

Data from ChEMBL 36 via Core Engine