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Compound Detail

CHEMBL116

AMPRENAVIR
💊 Approved Drug
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💊 Approved Drug
CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)c1ccc(N)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL116
Name AMPRENAVIR
Phase Approved
Structure Type MOL
InChI Key YMARZQAQMVYCKC-OEMFJLHTSA-N
Therapeutic ✓ Yes

Known Names

141 W94 141W94 Agenerase Amprenavir J05AE05 KVX-478 VX-478
16
Targets
302
Activities
4
Assay Types
15
PK Parameters
20
Publications
7
Known Names
3
Indications
1
Mechanisms

Molecular Properties

505.6
MW (Da)
2.40
ALogP
7
HBA
3
HBD
131.2
PSA (Ų)
0.40
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -vir
USAN Year 1997

Extended Properties

Molecular Formula C25H35N3O6S
MW 505.64
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness -0.20

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 Virus Diseases Acquired Immunodeficiency Syndrome

ATC Classification

J05AE05
amprenavir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 133 meas. best 8.74
IC50 107 meas. best 9.0
Ki 61 meas. best 10.52
Kd 1 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 10.52 9.2858 0.0 33
Protease
CHEMBL2366517
 Ki 10.44 8.9555 0.0 11
Unchecked
CHEMBL612545
 Ki 9.82 8.5567 0.1 12
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 9.0 7.194 1.0 5
Human immunodeficiency virus type 1 protease
CHEMBL243
 Kd 8.96 8.96 1.1 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.74 6.8731 1.8 120
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.7 6.8743 2.0 53
MT4
CHEMBL388
 EC50 8.0 8.0 10.0 1
Human immunodeficiency virus
CHEMBL613758
 IC50 7.7 6.9833 20.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.7 7.7 20.0 1
MT2
CHEMBL614184
 IC50 7.55 7.5033 28.0 3
Human immunodeficiency virus
CHEMBL613758
 EC50 7.48 7.48 33.0 1
Human immunodeficiency virus 2
CHEMBL380
 IC50 7.01 5.8626 98.0 23
MT4
CHEMBL388
 IC50 7.0 6.72 100.0 6
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.92 6.2982 120.0 11
Cytochrome P450 3A5
CHEMBL3019
 Ki 6.7 6.7 200.0 1
Cytochrome P450 3A4
CHEMBL340
 Ki 6.58 6.505 260.0 2
Unchecked
CHEMBL612545
 IC50 6.55 6.55 280.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 6.0 6.0 1000.0 1
Thromboxane-A synthase
CHEMBL1835
 IC50 5.17 5.17 6727.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.82 4.82 15170.0 1
Cathepsin D
CHEMBL2581
 IC50 4.82 4.82 15200.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.6 4.4333 25000.0 3
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.54 4.54 28480.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 44100.0 ng.hr.mL-1 Homo sapiens
AUC 26394.41 ng.hr.mL-1 Homo sapiens
CL 19.38 mL.min-1.kg-1 Homo sapiens
CL 0.6667 mL.min-1.kg-1 Homo sapiens
Cmax 12063.92 nM Homo sapiens
Cmax 15150.0 nM Homo sapiens
F 70.0 % Rattus norvegicus
F 0.3 % Canis lupus familiaris
Fu 0.92 - Homo sapiens
Fu 0.129 - Rattus norvegicus
Fu 0.204 - Rattus norvegicus
T1/2 10.0 hr -
T1/2 0.547 hr Homo sapiens
T1/2 15.8 hr Homo sapiens
T1/2 11.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus type 1 protease Ki = 0.03 nM 10.52 Inhibition of HIV1 protease I50V, A71V mutant by FRET assay 22708897
Protease Ki = 0.036 nM 10.44 Inhibition of HIV1 protease 17620375
Human immunodeficiency virus type 1 protease Ki = 0.04 nM 10.4 Inhibition of HIV protease 10866371
Human immunodeficiency virus type 1 protease Ki = 0.04 nM 10.4 Inhibition constant against HIV Protease 15582415
Human immunodeficiency virus type 1 protease Ki = 0.04 nM 10.4 Inhibition constant against HIV-1 protease 15975788
Human immunodeficiency virus type 1 protease Ki = 0.041 nM 10.39 Inhibition of HIV1 protease L10I, G48V, I54V, L63P and V82A mutant by FRET assay 22708897
Human immunodeficiency virus type 1 protease Ki = 0.057 nM 10.24 Inhibition of HIV-1 Protease activity 15013001
Protease Ki = 0.057 nM 10.24 Inhibition of HIV1 protease by fluorescent peptide substrate based assay 17620375
Human immunodeficiency virus type 1 protease Ki = 0.06 nM 10.22 Binding affinity for HIV-1 protease expressed in Escherichia coli upon incubatio... 16220977
Human immunodeficiency virus type 1 protease Ki = 0.08 nM 10.1 Binding affinity to HIV-1 protease assessed as inhibition constant incubated for... 35123178
Human immunodeficiency virus type 1 protease Ki = 0.1 nM 10.0 Inhibition of wild type HIV1 protease Q7K mutant 17149864
Protease Ki = 0.117 nM 9.93 Inhibition of HIV1 protease 17638694
Human immunodeficiency virus type 1 protease Ki = 0.13 nM 9.89 Inhibition of HIV1 recombinant protease D30N/N88D mutant expressed in Escherichi... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.13 nM 9.89 Inhibition of HIV1 recombinant protease L10F/L19I/K20R/L33F/E35D/M36I/R41K/F53L/... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.15 nM 9.82 Inhibition of HIV1 protease L10I/G48V/I54V/L63P/V82A mutant 17149864
Human immunodeficiency virus type 1 protease Ki = 0.15 nM 9.82 Inhibition of HIV1 recombinant protease L10I/I15V/E35D/N37S/R41K/I62V/L63P/A71V/... 18598016
Unchecked Ki = 0.15 nM 9.82 Inhibition of HIV1 Protease M1 variant by FRET based assay 17696512
Human immunodeficiency virus type 1 protease Ki = 0.16 nM 9.8 Binding affinity to inhibit the purified wild-type HIV-1 Protease 9003516
Human immunodeficiency virus type 1 protease Ki = 0.17 nM 9.77 Inhibitory activity against HIV-1 protease 8863807
Human immunodeficiency virus type 1 protease Ki = 0.17 nM 9.77 Affinity against HIV protease 9406598

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 202
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
17371811 10.1128/aac.01413-06 Human immunodeficiency virus 1 24
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 1 22
17981045 10.1016/j.bmc.2007.10.062 Human immunodeficiency virus 1 17
26799988 10.1021/acs.jmedchem.5b01697 Human immunodeficiency virus 1 17
19104010 10.1128/aac.00984-08 Human immunodeficiency virus 1 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19746963 10.1021/jm900695w Human immunodeficiency virus 1 13
11602674 - ATP-dependent translocase ABCB1 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
16913714 10.1021/jm060561m Human immunodeficiency virus 1 11
20034787 10.1016/j.bmcl.2009.11.123 Human immunodeficiency virus 1 11
21800876 10.1021/jm200649p Human immunodeficiency virus 1 10
17576848 10.1128/aac.00146-07 Human immunodeficiency virus 2 10
28195728 10.1021/acs.jmedchem.6b01767 Human immunodeficiency virus type 1 protease 10
17116674 10.1128/aac.00870-06 Human immunodeficiency virus 2 9

Data from ChEMBL 36 via Core Engine