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Compound Detail

CHEMBL82301

VICRIVIROC
🧪 Phase III
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🧪 Phase III
COC[C@@H](c1ccc(C(F)(F)F)cc1)N1CCN(C2(C)CCN(C(=O)c3c(C)ncnc3C)CC2)C[C@@H]1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL82301
Name VICRIVIROC
Phase Phase III
Structure Type MOL
InChI Key CNPVJJQCETWNEU-CYFREDJKSA-N

Known Names

MK-7690 SCH-417690 FREE BASE SCH-D Vicriviroc
4
Targets
24
Activities
3
Assay Types
30
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

533.6
MW (Da)
4.50
ALogP
6
HBA
0
HBD
61.8
PSA (Ų)
0.55
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -vir-; -vir-
USAN Year 2005

Extended Properties

Molecular Formula C28H38F3N5O2
MW 533.64
Aromatic Rings 2
Heavy Atoms 38
NP-Likeness -0.76

Indications

Acquired Immunodeficiency Syndrome HIV Infections Colorectal Neoplasms

Activity Summary

IC50 14 meas. best 9.64
EC50 8 meas. best 9.43
Ki 2 meas. best 8.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.64 8.9038 0.2 8
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.43 7.985 0.4 8
C-C chemokine receptor type 5
CHEMBL274
 IC50 9.35 8.93 0.5 3
Unchecked
CHEMBL612545
 IC50 9.34 8.93 0.5 2
C-C chemokine receptor type 5
CHEMBL3676
 IC50 9.04 9.04 0.9 1
C-C chemokine receptor type 5
CHEMBL274
 Ki 8.68 8.64 2.1 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 6500.0 ng.hr.mL-1 Rattus norvegicus
AUC 6900.0 ng.hr.mL-1 Rattus norvegicus
AUC 21000.0 ng.hr.mL-1 Rattus norvegicus
AUC 21000.0 ng.hr.mL-1 Rattus norvegicus
AUC 2240.0 ng.hr.mL-1 Cercopithecidae
AUC 1990.0 ng.hr.mL-1 Cercopithecidae
AUC 32200.0 ng.hr.mL-1 Homo sapiens
AUC 6670.0 ng.hr.mL-1 Homo sapiens
AUC 6050.0 ng.hr.mL-1 Homo sapiens
AUC 10100.0 ng.hr.mL-1 Homo sapiens
AUC 11000.0 ng.hr.mL-1 Homo sapiens
AUC 6060.0 ng.hr.mL-1 Homo sapiens
AUC 8140.0 ng.hr.mL-1 Homo sapiens
AUC 8750.0 ng.hr.mL-1 Homo sapiens
AUC 3260.0 ng.hr.mL-1 Homo sapiens
AUC 5390.0 ng.hr.mL-1 Homo sapiens
AUC 5050.0 ng.hr.mL-1 Homo sapiens
Cmax 4310.02 nM Rattus norvegicus
Cmax 1255.53 nM Cercopithecidae
Cmax 3560.45 nM Homo sapiens
Cmax 755.19 nM Homo sapiens
Cmax 1369.84 nM Homo sapiens
Cmax 2117.53 nM Homo sapiens
Cmax 1843.94 nM Homo sapiens
Cmax 1216.18 nM Homo sapiens
Cmax 1778.35 nM Homo sapiens
Cmax 1948.88 nM Homo sapiens
Cmax 888.24 nM Homo sapiens
Cmax 1570.35 nM Homo sapiens
Cmax 1482.27 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 IC50 = 0.23 nM 9.64 Antiviral activity against HIV-1 BaL infected in PHA-stimulated human PBMC cells... 24900235
Human immunodeficiency virus 1 EC50 = 0.37 nM 9.43 Antiviral activity against HIV1 JRCSF infected in human PBMC assessed as inhibit... 19451305
C-C chemokine receptor type 5 IC50 = 0.45 nM 9.35 Binding affinity to CCR5 22931505
Unchecked IC50 = 0.46 nM 9.34 Compound was tested for inhibiting the entry of replication deffective HIV-1 (YU... 15115380
Human immunodeficiency virus 1 IC50 = 0.52 nM 9.28 Antiviral activity against HIV1 19112024
Human immunodeficiency virus 1 IC50 = 0.56 nM 9.25 Antiviral activity against HIV-1 ADA infected in PHA-stimulated human PBMC cells... 24900235
Human immunodeficiency virus 1 IC50 = 0.6 nM 9.22 Inhibition of HIV-1 (ADA) entry into U-87 (human glioblastoma) cells. 12639564
C-C chemokine receptor type 5 IC50 = 0.91 nM 9.04 Displacement of [125I]-RANTES from CCR5 in mouse NIH/3T3 cells after 1 hr 29425816
Human immunodeficiency virus 1 EC50 = 1.2 nM 8.92 Antiviral activity against HIV1 R5 infected in human PBMC assessed as inhibition... 19451305
C-C chemokine receptor type 5 IC50 = 1.2 nM 8.92 Antagonist activity at CCR5 in IL-10 stimulated human PBMC cells assessed as MIP... 24900235
Human immunodeficiency virus 1 EC50 = 1.4 nM 8.85 Antiviral activity against R5 tropic HIV1 JR-CSF in PM1/CCR5 cells assessed as p... 22277590
C-C chemokine receptor type 5 Ki = 2.1 nM 8.68 Inhibition of [125I]RANTES binding to CCR5 receptor. 12639564
C-C chemokine receptor type 5 Ki = 2.5 nM 8.6 Antagonistic activity against C-C chemokine receptor type 5 15115380
Human immunodeficiency virus 1 IC50 = 3.0 nM 8.52 Antiviral activity against multidrug-resistant R5 tropic HIV1 MM infected in hum... 21256008
C-C chemokine receptor type 5 IC50 = 3.0 nM 8.52 Displacement of [125I]MIP-1beta from CCR5 in IL-10-stimulated human monocytes 24900235
Human immunodeficiency virus 1 IC50 = 3.0 nM 8.52 Antiviral activity against R5 tropic multidrug-resistant HIV1 MM infected PBMC a... 21658961
Unchecked IC50 = 3.0 nM 8.52 Inhibition of CXCR4-Y251A mutant (unknown origin) 28165741
Human immunodeficiency virus 1 IC50 = 4.0 nM 8.4 Antiviral activity against R5 tropic HIV1 Ba-L infected in human PBMC assessed a... 21256008
Human immunodeficiency virus 1 IC50 = 4.0 nM 8.4 Antiviral activity against R5 tropic HIV1 Ba-L infected PBMC assessed as inhibit... 21658961
Human immunodeficiency virus 1 EC50 = 4.9 nM 8.31 Antiviral activity against macrophage-tropic HIV1 NL(AD8) infected in human PM1 ... 26094944

Literature References

PubMed DOI Target Context # Activities
20350942 10.1128/aac.01447-09 Homo sapiens 76
15115380 10.1021/jm0304515 ADMET 10
19451305 10.1128/aac.01727-08 Human immunodeficiency virus 1 8
15115380 10.1021/jm0304515 Rattus norvegicus 6
22277590 10.1016/j.bmc.2011.12.055 Human immunodeficiency virus 1 3
21658961 10.1016/j.bmc.2011.05.022 Human immunodeficiency virus 1 3
26094944 10.1016/j.bmc.2015.06.020 Human immunodeficiency virus 1 3
21128663 10.1021/jm100978n Human immunodeficiency virus 1 3
32305183 10.1016/j.bmc.2020.115488 Human immunodeficiency virus 1 2
26094944 10.1016/j.bmc.2015.06.020 MT4 2
24900235 10.1021/ml1001536 Human immunodeficiency virus 1 2
24900235 10.1021/ml1001536 C-C chemokine receptor type 5 2
21256008 10.1016/j.bmcl.2010.12.109 Human immunodeficiency virus 1 2
33316719 10.1016/j.bmc.2020.115923 Human immunodeficiency virus 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
32305183 10.1016/j.bmc.2020.115488 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
15115380 10.1021/jm0304515 Muscarinic acetylcholine receptor M2 1
15115380 10.1021/jm0304515 Muscarinic acetylcholine receptor M1 1
28165741 10.1021/acs.jmedchem.6b01309 Unchecked 1

Data from ChEMBL 36 via Core Engine