Compound Detail
CHEMBL729
LOPINAVIR 💊 Approved Drug
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💊 Approved Drug
Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)N1CCCNC1=O
Basic Information
| ChEMBL ID | CHEMBL729 |
| Name | LOPINAVIR |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | KJHKTHWMRKYKJE-SUGCFTRWSA-N |
| Therapeutic | ✓ Yes |
25
Targets
293
Activities
4
Assay Types
30
PK Parameters
20
Publications
10
Known Names
17
Indications
1
Mechanisms
Molecular Properties
628.8
MW (Da)
4.33
ALogP
5
HBA
4
HBD
120.0
PSA (Ų)
0.20
QED
1
Ro5 Violations
15
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 2000 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Human immunodeficiency virus type 1 protease inhibitor | INHIBITOR | Human immunodeficiency virus type 1 protease | ✓ | ✓ |
Indications
HIV Infections HIV Infections Acquired Immunodeficiency Syndrome Coronavirus Infections Coronavirus Infections Influenza, Human Pneumonia Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Infections Pregnancy Sarcoma, Kaposi Anus Neoplasms Hepatitis C Insulin Resistance Respiratory Distress Syndrome Tuberculosis
Activity Summary
EC50 173 meas. best 9.0
IC50 80 meas. best 9.0
Ki 37 meas. best 10.85
Kd 3 meas. best 10.0
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Protease CHEMBL2366517 | Ki | 10.85 | 10.31 | 0.0 | 7 |
| Human immunodeficiency virus type 1 protease CHEMBL243 | Ki | 10.59 | 9.7209 | 0.0 | 11 |
| Unchecked CHEMBL612545 | Ki | 10.4 | 8.5155 | 0.0 | 11 |
| Human immunodeficiency virus type 1 protease CHEMBL243 | Kd | 10.0 | 10.0 | 0.1 | 1 |
| Human immunodeficiency virus 1 CHEMBL378 | IC50 | 9.0 | 7.3532 | 1.0 | 19 |
| Human immunodeficiency virus 1 CHEMBL378 | EC50 | 9.0 | 7.0268 | 1.0 | 136 |
| Protease CHEMBL2366517 | Kd | 8.96 | 8.96 | 1.1 | 1 |
| Protease CHEMBL2366517 | IC50 | 8.6 | 7.85 | 2.5 | 4 |
| Human immunodeficiency virus 2 CHEMBL380 | EC50 | 8.59 | 7.5307 | 2.6 | 15 |
| Human immunodeficiency virus 2 CHEMBL380 | IC50 | 8.4 | 6.9922 | 4.0 | 27 |
| Unchecked CHEMBL612545 | IC50 | 7.8 | 7.7 | 16.0 | 2 |
| Human immunodeficiency virus type 1 protease CHEMBL243 | IC50 | 7.6 | 7.6 | 25.0 | 1 |
| NON-PROTEIN TARGET CHEMBL3879801 | IC50 | 7.52 | 6.12 | 30.0 | 2 |
| Human immunodeficiency virus CHEMBL613758 | EC50 | 7.5 | 6.63 | 32.0 | 3 |
| MT4 CHEMBL388 | IC50 | 7.46 | 6.5025 | 35.0 | 4 |
| Human immunodeficiency virus CHEMBL613758 | IC50 | 7.4 | 6.9 | 40.0 | 2 |
| MT4 CHEMBL388 | EC50 | 7.0 | 6.996 | 100.0 | 5 |
| Cytochrome P450 3A4 CHEMBL340 | Ki | 6.39 | 6.13 | 410.0 | 3 |
| Protease CHEMBL2366517 | EC50 | 5.94 | 5.94 | 1160.0 | 1 |
| ATP-dependent translocase ABCB1 CHEMBL4302 | IC50 | 5.77 | 5.38 | 1700.0 | 2 |
| Plasmodium falciparum CHEMBL364 | IC50 | 5.72 | 5.645 | 1920.0 | 2 |
| Plasmodium falciparum CHEMBL364 | EC50 | 5.7 | 5.64 | 2000.0 | 3 |
| SARS-CoV-2 CHEMBL4303835 | EC50 | 5.3 | 4.925 | 5000.0 | 4 |
| Human coronavirus 229E CHEMBL613837 | EC50 | 5.18 | 5.18 | 6600.0 | 2 |
| Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393 | IC50 | 5.12 | 5.12 | 7600.0 | 1 |
| Middle East respiratory syndrome-related coronavirus CHEMBL4296578 | EC50 | 5.1 | 5.1 | 8000.0 | 1 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240 | IC50 | 5.07 | 5.07 | 8511.4 | 1 |
| SARS-CoV-2 CHEMBL4303835 | IC50 | 5.04 | 4.8175 | 9120.0 | 4 |
| Replicase polyprotein 1ab CHEMBL4523582 | IC50 | 5.04 | 5.04 | 9120.0 | 1 |
| Trypanosoma brucei rhodesiense CHEMBL612348 | IC50 | 4.97 | 4.97 | 10810.0 | 1 |
| Leishmania donovani CHEMBL367 | IC50 | 4.93 | 4.93 | 11830.0 | 1 |
| Trypanosoma cruzi CHEMBL368 | IC50 | 4.81 | 4.81 | 15380.0 | 1 |
| SARS-CoV CHEMBL4303836 | EC50 | 4.77 | 4.77 | 17100.0 | 2 |
| Bile salt export pump CHEMBL6020 | IC50 | 4.76 | 4.76 | 17300.0 | 2 |
| CAAX prenyl protease 1 homolog CHEMBL1075286 | IC50 | 4.74 | 4.74 | 18400.0 | 1 |
| ATP-binding cassette sub-family C member 3 CHEMBL5918 | IC50 | 4.68 | 4.68 | 21000.0 | 1 |
| Unchecked CHEMBL612545 | EC50 | 4.58 | 4.58 | 26630.0 | 1 |
| ATP-binding cassette sub-family C member 4 CHEMBL1743128 | IC50 | 4.33 | 4.33 | 47000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 9280.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 11260.0 | ng.hr.mL-1 | Canis lupus familiaris |
| AUC | 99700.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 59726.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 48465.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 157200.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 151810.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 99603.5 | ng.hr.mL-1 | Homo sapiens |
| AUC | 9280.0 | ng.hr.mL-1 | Rattus norvegicus |
| CL | 2.58 | L/hr | Homo sapiens |
| CL | 2.61 | L/hr | Homo sapiens |
| CL | 544.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 1.6 | mL.min-1.g-1 | Homo sapiens |
| CL | 2.7 | mL.min-1.g-1 | Homo sapiens |
| Cmax | 159.03 | nM | - |
| Cmax | 8746.68 | nM | - |
| Cmax | 2464.97 | nM | Rattus norvegicus |
| Cmax | 3975.76 | nM | Canis lupus familiaris |
| Cmax | 17763.71 | nM | Homo sapiens |
| Cmax | 10888.82 | nM | Homo sapiens |
| Cmax | 8352.28 | nM | Homo sapiens |
| Cmax | 27353.25 | nM | Homo sapiens |
| Cmax | 25524.4 | nM | Homo sapiens |
| Cmax | 159030.55 | nM | Homo sapiens |
| Cmax | 8746680.24 | nM | Homo sapiens |
| T1/2 | 8.21 | hr | Homo sapiens |
| T1/2 | 6.56 | hr | Homo sapiens |
| T1/2 | 0.22 | hr | Bos taurus |
| T1/2 | 101.0 | hr | - |
| T1/2 | 5.4 | hr | - |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 17638694 | 10.1128/aac.00149-07 | Human immunodeficiency virus 1 | 53 |
| 18227188 | 10.1128/aac.01284-07 | Human immunodeficiency virus 2 | 36 |
| 17101675 | 10.1128/aac.00690-06 | Human immunodeficiency virus 1 | 33 |
| 18955518 | 10.1128/aac.00689-08 | Human immunodeficiency virus 1 | 33 |
| 26799988 | 10.1021/acs.jmedchem.5b01697 | Human immunodeficiency virus 1 | 32 |
| 20308382 | 10.1128/aac.01784-09 | Human immunodeficiency virus 1 | 31 |
| 18212102 | 10.1128/aac.01132-07 | Human immunodeficiency virus 1 | 29 |
| 17371811 | 10.1128/aac.01413-06 | Human immunodeficiency virus 1 | 24 |
| 19104010 | 10.1128/aac.00984-08 | Human immunodeficiency virus 1 | 23 |
| 28418652 | 10.1021/acs.jmedchem.7b00172 | Human immunodeficiency virus 1 | 21 |
| 20439612 | 10.1128/aac.01766-09 | Human immunodeficiency virus 1 | 18 |
| 17576848 | 10.1128/aac.00146-07 | Human immunodeficiency virus 2 | 17 |
| 17981045 | 10.1016/j.bmc.2007.10.062 | Human immunodeficiency virus 1 | 17 |
| 19746963 | 10.1021/jm900695w | Human immunodeficiency virus 1 | 13 |
| 15646539 | 10.1016/s0399-8320(04)95062-2 | Unchecked | 11 |
| 18411323 | 10.1128/aac.01565-07 | Homo sapiens | 10 |
| 21149628 | 10.1128/aac.01228-10 | Human immunodeficiency virus 1 | 10 |
| 19237646 | 10.1128/aac.01091-08 | Serum | 10 |
| 20404123 | 10.1128/aac.01828-09 | Human immunodeficiency virus 1 | 10 |
| 20028821 | 10.1128/aac.01512-09 | Plasmodium falciparum | 10 |
Data from ChEMBL 36 via Core Engine