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Compound Detail

CHEMBL222559

TIPRANAVIR
💊 Approved Drug
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💊 Approved Drug
CCC[C@@]1(CCc2ccccc2)CC(O)=C([C@H](CC)c2cccc(NS(=O)(=O)c3ccc(C(F)(F)F)cn3)c2)C(=O)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL222559
Name TIPRANAVIR
Phase Approved
Structure Type MOL
InChI Key SUJUHGSWHZTSEU-FYBSXPHGSA-N
Therapeutic ✓ Yes

Known Names

Aptivus Tipranavir U-140690
14
Targets
93
Activities
3
Assay Types
9
PK Parameters
20
Publications
3
Known Names
3
Indications
1
Mechanisms

Molecular Properties

602.7
MW (Da)
7.33
ALogP
6
HBA
2
HBD
105.6
PSA (Ų)
0.22
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -vir
USAN Year 1998

Extended Properties

Molecular Formula C31H33F3N2O5S
MW 602.68
Aromatic Rings 3
Heavy Atoms 42
NP-Likeness -0.52

Mechanism of Action

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

Indications

Hemorrhage HIV Infections Virus Diseases

ATC Classification

J05AE09
tipranavir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

EC50 43 meas. best 7.66
IC50 40 meas. best 9.0
Ki 10 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.0 7.4433 1.0 6
HIV-1 protease
CHEMBL4296312
 IC50 8.14 8.14 7.2 1
Unchecked
CHEMBL612545
 Ki 8.1 8.1 8.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.66 6.5557 22.0 35
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 7.52 7.52 30.0 2
Human immunodeficiency virus
CHEMBL613758
 IC50 7.52 7.52 30.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.3 7.3 50.0 1
Human immunodeficiency virus 2
CHEMBL380
 IC50 6.84 6.0256 145.0 27
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.52 6.5 300.0 2
CAAX prenyl protease 1 homolog
CHEMBL1075286
 IC50 5.92 5.92 1200.0 1
Pepsin A
CHEMBL3295
 Ki 5.7 5.7 2000.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.13 5.13 7380.0 1
Cathepsin E
CHEMBL3092
 Ki 5.05 5.05 9000.0 1
Plasmodium falciparum
CHEMBL364
 EC50 4.92 4.7625 12000.0 4
Cathepsin D
CHEMBL2581
 Ki 4.82 4.82 15000.0 1
Homo sapiens
CHEMBL372
 EC50 4.22 4.145 60000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 395960.76 ng.hr.mL-1 Homo sapiens
CL 2.833 mL.min-1.kg-1 Rattus norvegicus
CL 1.47 L/hr Homo sapiens
Cmax 99390.0 nM Homo sapiens
F 30.0 % Rattus norvegicus
T1/2 5.4 hr Rattus norvegicus
T1/2 4.6 hr Homo sapiens
Tmax 2.9 hr Homo sapiens
Vd 9.6 l Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 IC50 = 1.0 nM 9.0 Antiviral activity against HIV1 isolate 5512 with D30N, M461 and V771 mutation i... 17116674
HIV-1 protease IC50 = 7.2 nM 8.14 Enzyme Inhibition of Purified HIV-1 Protease: Protease inhibitors (PI) are used ... -
Unchecked Ki = 8.0 nM 8.1 Binding affinity to HIV protease assessed as inhibition constant 37393791
Human immunodeficiency virus 1 EC50 = 22.0 nM 7.66 Antiviral activity against HIV1 expressing protease L10I/G48V/I54V/A71V/I84V/L90... 20439612
Human immunodeficiency virus 1 EC50 = 29.0 nM 7.54 Antiviral activity against HIV1 expressing protease L10I/L24I/M46I/V82I/I84V mut... 20439612
Human immunodeficiency virus 1 IC50 = 30.0 nM 7.52 Antiviral activity against HIV-1 IIIB infected in human H9 cells 37393791
Human immunodeficiency virus type 1 protease IC50 = 30.0 nM 7.52 Tested for inhibition of HIV protease 8893827
Human immunodeficiency virus type 1 protease IC50 = 30.0 nM 7.52 Inhibition of HIV-1 protease in a cell culture assay using HIV-1 IIIB infected H... 9719600
Human immunodeficiency virus IC50 = 30.0 nM 7.52 Antiviral activity against HIV 37393791
Human immunodeficiency virus 1 EC50 = 37.0 nM 7.43 Antiviral activity against HIV1 expressing protease L10F/M46L/I50V/A71Vmutant in... 20439612
Human immunodeficiency virus 1 EC50 = 39.0 nM 7.41 Antiviral activity against HIV1 expressing protease L10F/D30N/K45I/A71V/T74S mut... 20439612
Human immunodeficiency virus 1 EC50 = 40.9 nM 7.39 Antiviral activity against HIV1 HXB2 in human MT4 cells assessed as inhibition o... 17620375
Human immunodeficiency virus 1 IC50 = 42.0 nM 7.38 Antiviral activity against HIV1 isolate 5512 with V321 and M46L mutation in CBMC... 17116674
Human immunodeficiency virus 1 EC50 = 42.0 nM 7.38 Antiviral activity against HIV1 expressing protease L10F/M46M,I/Q61Q mutant infe... 20439612
NON-PROTEIN TARGET IC50 = 50.0 nM 7.3 Antiviral activity against Human immunodeficiency virus type 1 (BRU ISOLATE) aft... 18227188
Human immunodeficiency virus 1 EC50 = 66.0 nM 7.18 Antiviral activity against wild-type HIV1 pNL4-3 infected in human MT4 cells ass... 18212102
Human immunodeficiency virus 1 EC50 = 76.2 nM 7.12 Antiviral activity against HIV1 NL4-3 17620375
Human immunodeficiency virus 1 IC50 = 92.0 nM 7.04 Antiviral activity against wild type HIV1 in CBMCs 17116674
Human immunodeficiency virus 1 EC50 = 95.0 nM 7.02 Antiviral activity against HIV1 expressing protease L10F/M46I/T91S mutant infect... 20439612
Human immunodeficiency virus 1 IC50 = 100.0 nM 7.0 Antiviral activity against HIV1 LAI in MT2 cells 17635930

Literature References

PubMed DOI Target Context # Activities
18227188 10.1128/aac.01284-07 Human immunodeficiency virus 2 36
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 1 18
17620375 10.1128/aac.00401-07 Human immunodeficiency virus 1 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20028821 10.1128/aac.01512-09 Plasmodium falciparum 12
18212102 10.1128/aac.01132-07 Human immunodeficiency virus 1 12
17116674 10.1128/aac.00870-06 Human immunodeficiency virus 2 9
17485497 10.1128/aac.01115-06 Homo sapiens 8
20805393 10.1128/aac.00906-10 Human immunodeficiency virus 1 6
17664327 10.1128/aac.00671-07 Homo sapiens 6
15771440 10.1021/jm049454n Human immunodeficiency virus 1 6
8893827 10.1021/jm960541s Human immunodeficiency virus type 1 protease 5
17116674 10.1128/aac.00870-06 Human immunodeficiency virus 1 4
9719600 10.1021/jm9802158 Human immunodeficiency virus type 1 protease 3
8893827 10.1021/jm960541s Rattus norvegicus 3
21149628 10.1128/aac.01228-10 Human immunodeficiency virus 1 3
37393791 10.1016/j.ejmech.2023.115586 Human immunodeficiency virus 1 2
15582426 10.1016/j.bmcl.2004.10.018 Human immunodeficiency virus type 1 protease 2
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 2 2
20028821 10.1128/aac.01512-09 Homo sapiens 2

Data from ChEMBL 36 via Core Engine