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Compound Detail

CHEMBL2105686

CENICRIVIROC MESYLATE
Phase I
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Phase I
CCCCOCCOc1ccc(-c2ccc3c(c2)/C=C(/C(=O)Nc2ccc([S@@+]([O-])Cc4cncn4CCC)cc2)CCCN3CC(C)C)cc1.CS(=O)(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2105686
Name CENICRIVIROC MESYLATE
Phase Phase I
Structure Type MOL
InChI Key IXPBPUPDRDCRSY-YLZLUMLXSA-N
Parent Compound CHEMBL2110727
Active Moiety CHEMBL2110727

Known Names

Cenicriviroc mesilate Cenicriviroc mesylate TAK-652 TBR-652
5
Targets
16
Activities
1
Assay Types
18
PK Parameters
11
Publications
4
Known Names
1
Indications

Molecular Properties

697.0
MW (Da)
8.74
ALogP
7
HBA
1
HBD
91.7
PSA (Ų)
0.09
QED
2
Ro5 Violations
17
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -vir-; -vir-
USAN Year 2010

Extended Properties

Molecular Formula C42H56N4O7S2
MW 793.06
Aromatic Rings 4
Heavy Atoms 50
NP-Likeness -0.84

Indications

HIV Infections

Activity Summary

IC50 16 meas. best 10.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 IC50 10.62 9.79 0.0 10
C-C chemokine receptor type 5
CHEMBL274
 IC50 10.0 9.4033 0.1 3
C-C chemokine receptor type 2
CHEMBL4015
 IC50 8.23 8.23 5.9 1
C-C chemokine receptor type 4
CHEMBL2414
 IC50 5.96 5.96 1100.0 1
C-C chemokine receptor type 3
CHEMBL3473
 IC50 5.62 5.62 2400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 7610.0 ng.hr.mL-1 Rattus norvegicus
AUC 2310.0 ng.hr.mL-1 Canis lupus familiaris
AUC 1450.0 ng.hr.mL-1 Macaca fascicularis
AUC 2320.0 ng.hr.mL-1 Rattus norvegicus
AUC 6010.0 ng.hr.mL-1 Canis lupus familiaris
AUC 670.0 ng.hr.mL-1 Macaca fascicularis
Cmax 695.88 nM Rattus norvegicus
Cmax 817.84 nM Canis lupus familiaris
Cmax 166.44 nM Macaca fascicularis
F 10.2 % Rattus norvegicus
F 88.5 % Canis lupus familiaris
F 15.6 % Macaca fascicularis
T1/2 4.85 hr Rattus norvegicus
T1/2 5.04 hr Canis lupus familiaris
T1/2 6.09 hr Macaca fascicularis
Tmax 1.3 hr Rattus norvegicus
Tmax 2.7 hr Canis lupus familiaris
Tmax 2.0 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 IC50 = 0.024 nM 10.62 Inhibition of replication of R5 HIV1 HHA in PMBC 16539392
Human immunodeficiency virus 1 IC50 = 0.043 nM 10.37 Inhibition of replication of R5 HIV1 KK in PMBC 16539392
Human immunodeficiency virus 1 IC50 = 0.049 nM 10.31 Inhibition of replication of R5 HIV1 HKW in PMBC 16539392
Human immunodeficiency virus 1 IC50 = 0.07 nM 10.15 Inhibition of replication of R5 HIV1 CTV in PMBC 16539392
Human immunodeficiency virus 1 IC50 = 0.087 nM 10.06 Inhibition of replication of R5 HIV1 HNK in PMBC 16539392
Human immunodeficiency virus 1 IC50 = 0.089 nM 10.05 Inhibition of replication of R5 HIV1 HTN in PMBC 16539392
C-C chemokine receptor type 5 IC50 = 0.1 nM 10.0 Inhibition of membrane fusion between HIV1 JR-FL Env-expressing COS7 cells and M... 16539392
Human immunodeficiency virus 1 IC50 = 0.14 nM 9.85 Inhibition of HIV1 KK infected PBMC 17116673
C-C chemokine receptor type 5 IC50 = 0.2 nM 9.7 Inhibition of replication of R5 HIV1 Ba-L in MOLT4/CCR5 cells 16539392
Human immunodeficiency virus 1 IC50 = 0.2 nM 9.7 Antiviral activity in long term culture of HIV1 KK infected PBMCs after 43 passa... 17116673
Human immunodeficiency virus 1 IC50 = 0.24 nM 9.62 Antiviral activity in long term culture of HIV1 KK infected PBMCs after 8 passag... 17116673
C-C chemokine receptor type 5 IC50 = 3.1 nM 8.51 Displacement of [125I]RANTES from CCR5 expressed in CHO cells 16539392
C-C chemokine receptor type 2 IC50 = 5.9 nM 8.23 Displacement of [125I]MCP-1 from CCR2b expressed in CHO cells 16539392
Human immunodeficiency virus 1 IC50 = 67.0 nM 7.17 Antiviral activity in long term culture of HIV1 KK infected PBMCs after 56 passa... 17116673
C-C chemokine receptor type 4 IC50 = 1100.0 nM 5.96 Displacement of [125I]TARC from CCR4 expressed in CHO cells 16539392
C-C chemokine receptor type 3 IC50 = 2400.0 nM 5.62 Displacement of [125I]eotaxin from CCR3 expressed in CHO cells 16539392

Literature References

PubMed DOI Target Context # Activities
16539392 10.1021/jm0509703 Human immunodeficiency virus 1 12
17116673 10.1128/aac.01079-06 Human immunodeficiency virus 1 8
16539392 10.1021/jm0509703 Rattus norvegicus 7
16539392 10.1021/jm0509703 Canis familiaris 7
16539392 10.1021/jm0509703 Cynomolgus monkey 7
16539392 10.1021/jm0509703 C-C chemokine receptor type 5 4
16539392 10.1021/jm0509703 C-C chemokine receptor type 1 1
16539392 10.1021/jm0509703 C-C chemokine receptor type 2 1
16539392 10.1021/jm0509703 C-C chemokine receptor type 3 1
16539392 10.1021/jm0509703 C-C chemokine receptor type 4 1
16539392 10.1021/jm0509703 C-C chemokine receptor type 7 1

Data from ChEMBL 36 via Core Engine