Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL206031

BRECANAVIR
🧪 Phase II
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
🧪 Phase II
Cc1nc(COc2ccc(C[C@H](NC(=O)O[C@H]3CO[C@H]4OCC[C@H]43)[C@H](O)CN(CC(C)C)S(=O)(=O)c3ccc4c(c3)OCO4)cc2)cs1

Basic Information

ChEMBL ID CHEMBL206031
Name BRECANAVIR
Phase Phase II
Structure Type MOL
InChI Key JORVRJNILJXMMG-OLNQLETPSA-N

Known Names

Brecanavir GW-640385 GW-640385X GW-64085X GW640385 GW64085X
4
Targets
29
Activities
3
Assay Types
21
PK Parameters
20
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

703.8
MW (Da)
3.87
ALogP
12
HBA
2
HBD
155.0
PSA (Ų)
0.25
QED
2
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir
USAN Year 2005

Extended Properties

Molecular Formula C33H41N3O10S2
MW 703.84
Aromatic Rings 3
Heavy Atoms 48
NP-Likeness -0.39

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

Activity Summary

IC50 13 meas. best 9.7
EC50 12 meas. best 9.74
Ki 4 meas. best 6.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 9.74 9.0958 0.2 12
Human immunodeficiency virus 1
CHEMBL378
IC50 9.7 9.7 0.2 1
MT4
CHEMBL388
IC50 9.66 8.8927 0.2 11
Unchecked
CHEMBL612545
Ki 6.46 6.46 350.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 4.62 4.62 24100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 199.0 ng.hr.mL-1 Homo sapiens
AUC 1960.0 ng.hr.mL-1 Rattus norvegicus
CL 10.0 mL.min-1.kg-1 Rattus norvegicus
CL 19.0 mL.min-1.kg-1 Canis lupus familiaris
CL 5.4 mL.min-1.kg-1 Rattus norvegicus
CL 65.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 5.626 nM Homo sapiens
Cmax 69.9 nM Homo sapiens
Cmax 988.86 nM Rattus norvegicus
F 62.0 % Rattus norvegicus
F 86.0 % Canis lupus familiaris
F 10.0 % Rattus norvegicus
F 20.0 % Canis lupus familiaris
T1/2 1.1 hr Rattus norvegicus
T1/2 1.2 hr Canis lupus familiaris
T1/2 1.4 hr Rattus norvegicus
T1/2 0.87 hr Canis lupus familiaris
T1/2 2.2 hr Rattus norvegicus
T1/2 0.2 hr Rattus norvegicus
Tmax 2.5 hr Homo sapiens
Tmax 3.75 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.18 nM 9.74 Antiviral activity against HIV1 NL4-3 17620375
Human immunodeficiency virus 1 EC50 = 0.2 nM 9.7 Antiviral activity against HIV1 3B in human PBMC assessed as blockade of reverse... 17620375
Human immunodeficiency virus 1 IC50 = 0.2 nM 9.7 Antiviral activity against HIV1 LAI in MT2 cells 17635930
MT4 IC50 = 0.22 nM 9.66 Antiviral activity against HIV1 I54V in MT4 cells 16458505
Human immunodeficiency virus 1 EC50 = 0.42 nM 9.38 Antiviral activity against HIV1 BaL in human PBMC assessed as blockade of revers... 17620375
Human immunodeficiency virus 1 EC50 = 0.44 nM 9.36 Antiviral activity against HIV1 3B in human MT4 cells assessed as inhibition of ... 17620375
MT4 IC50 = 0.45 nM 9.35 Antiviral activity against nelfinavir resistant HIV1 14330 in MT4 cells 16458505
MT4 IC50 = 0.46 nM 9.34 Antiviral activity against indinavir resistant HIV1 30813 in MT4 cells 16458505
Human immunodeficiency virus 1 EC50 = 0.53 nM 9.28 Antiviral activity against HIV1 HXB2 in human MT4 cells assessed as inhibition o... 17620375
Human immunodeficiency virus 1 EC50 = 0.7 nM 9.15 Antiviral activity against HIV1 HXB2 in human MT4 cells assessed as inhibition o... 17620375
MT4 IC50 = 0.7 nM 9.15 Antiviral activity against HIV1 HXB2 in MT4 cells 16458505
MT4 IC50 = 0.77 nM 9.11 Antiviral activity against multi PI resistant HIV1 EP14 in MT4 cells 16458505
Human immunodeficiency virus 1 EC50 = 0.88 nM 9.06 Antiviral activity against HIV1 drug resistant mutant isolates from protease inh... 17620375
Human immunodeficiency virus 1 EC50 = 1.1 nM 8.96 Antiviral activity against HIV1 HXB2 in human MT4 cells assessed as inhibition o... 17620375
MT4 IC50 = 1.1 nM 8.96 Antiviral activity against HIV1 EP13 in MT4 cells 16458505
Human immunodeficiency virus 1 EC50 = 1.4 nM 8.85 Antiviral activity against HIV1 HXB2 in human MT4 cells assessed as inhibition o... 17620375
MT4 IC50 = 1.6 nM 8.8 Antiviral activity against HIV1 I50V in MT4 cells 16458505
MT4 IC50 = 1.7 nM 8.77 Antiviral activity against multi PI resistant HIV1 31246 in MT4 cells 16458505
Human immunodeficiency virus 1 EC50 = 2.2 nM 8.66 Antiviral activity against HIV1 HXB2 in human MT4 cells assessed as inhibition o... 17620375
Human immunodeficiency virus 1 EC50 = 2.6 nM 8.59 Antiviral activity against HIV1 HXB2 in human MT4 cells assessed as inhibition o... 17620375

Literature References

PubMed DOI Target Context # Activities
17620375 10.1128/aac.00401-07 Human immunodeficiency virus 1 21
16458505 10.1016/j.bmcl.2006.01.035 MT4 11
17261626 10.1128/aac.01005-06 Homo sapiens 7
23474906 10.1016/j.ejmech.2013.02.001 Rattus norvegicus 6
16458505 10.1016/j.bmcl.2006.01.035 Rattus norvegicus 5
16458505 10.1016/j.bmcl.2006.01.035 Canis familiaris 5
17664327 10.1128/aac.00671-07 ATP-dependent translocase ABCB1 4
17664327 10.1128/aac.00671-07 Homo sapiens 3
17635930 10.1074/jbc.m703938200 Protease 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
28865281 10.1016/j.ejmech.2017.07.044 ADMET 2
17635930 10.1074/jbc.m703938200 Human immunodeficiency virus 1 1
17664327 10.1128/aac.00671-07 Unchecked 1
16458505 10.1016/j.bmcl.2006.01.035 Human immunodeficiency virus type 1 protease 1
17620375 10.1128/aac.00401-07 Unchecked 1
17620375 10.1128/aac.00401-07 MT4 1
17620375 10.1128/aac.00401-07 MOLT-4 1
17620375 10.1128/aac.00401-07 ADMET 1
17620375 10.1128/aac.00401-07 U-937 1
17620375 10.1128/aac.00401-07 Plasma 1

Data from ChEMBL 36 via Core Engine