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Compound Detail

CHEMBL2178578

VERCIRNON
🧪 Phase III
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🧪 Phase III
CC(C)(C)c1ccc(S(=O)(=O)Nc2ccc(Cl)cc2C(=O)c2cc[n+]([O-])cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2178578
Name VERCIRNON
Phase Phase III
Structure Type MOL
InChI Key JRWROCIMSDXGOZ-UHFFFAOYSA-N

Known Names

CCX-282-B CCX282 GSK-1605786 GSK1605786 Vercirnon Verecimon
3
Targets
13
Activities
4
Assay Types
9
PK Parameters
20
Publications
6
Known Names
3
Indications
1
Mechanisms

Molecular Properties

444.9
MW (Da)
4.30
ALogP
4
HBA
1
HBD
90.2
PSA (Ų)
0.36
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -cirnon
USAN Year 2011

Extended Properties

Molecular Formula C22H21ClN2O4S
MW 444.94
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.69

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
C-C chemokine receptor type 9 antagonist ANTAGONIST C-C chemokine receptor type 9 ✓ ✓

Indications

Celiac Disease Colitis, Ulcerative Crohn Disease

Activity Summary

IC50 8 meas. best 8.59
Ki 3 meas. best 8.96
EC50 1 meas. best 8.55
Kd 1 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-C chemokine receptor type 2
CHEMBL4015
 Kd 10.0 10.0 0.1 1
C-C chemokine receptor type 9
CHEMBL5815
 Ki 8.96 8.4633 1.1 3
C-C chemokine receptor type 9
CHEMBL5815
 IC50 8.59 8.055 2.6 8
BaF3
CHEMBL614524
 EC50 8.55 8.55 2.8 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 340.0 ng.hr.mL-1 Mus musculus
CL 6.0 mL.min-1.kg-1 Homo sapiens
CL 147.0 mL.min-1.kg-1 Mus musculus
CL 33.0 mL.min-1.kg-1 Mus musculus
CL 103.0 mL.min-1.kg-1 Mus musculus
F 10.0 % Mus musculus
F 22.0 % Mus musculus
T1/2 1.3 hr Mus musculus
T1/2 0.16 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-C chemokine receptor type 2 Kd = 0.1 nM 10.0 Binding affinity to CCR2 (unknown origin) assessed as dissociation constant 28165741
C-C chemokine receptor type 9 Ki = 1.1 nM 8.96 Antagonist activity at CCR9 receptor in human MOLT4 cells assessed as inhibition... 26987013
C-C chemokine receptor type 9 IC50 = 2.6 nM 8.59 Antagonist activity at recombinant human CCR9B expressed in BAF3 cells assessed ... 31703817
BaF3 EC50 = 2.8 nM 8.55 Inhibition of chemotaxis in mouse BAF3 cells 31266686
C-C chemokine receptor type 9 IC50 = 2.8 nM 8.55 Antagonist activity at CCR9 assessed as inhibition of CCL25-induced chemotaxis b... 22931505
C-C chemokine receptor type 9 IC50 = 2.8 nM 8.55 Antagonist activity at recombinant human CCR9A expressed in BAF3 cells assessed ... 31703817
C-C chemokine receptor type 9 Ki = 3.7 nM 8.43 Antagonist activity at CCR9A receptor (unknown origin) overexpressed in human MO... 26987013
C-C chemokine receptor type 9 IC50 = 5.0 nM 8.3 Antagonist activity at CCR9 (unknown origin) assessed as inhibition of TECK-stim... 27256913
C-C chemokine receptor type 9 IC50 = 6.0 nM 8.22 Binding affinity to CCR9 22931505
C-C chemokine receptor type 9 IC50 = 10.0 nM 8.0 Antagonist activity at CCR9 receptor (unknown origin) assessed as inhibition of ... 26117562
C-C chemokine receptor type 9 Ki = 10.0 nM 8.0 Antagonist activity at CCR9 receptor in human MOLT4 cells assessed as inhibition... 26987013
C-C chemokine receptor type 9 IC50 = 11.0 nM 7.96 Antagonist activity at CCR9 receptor (unknown origin) by buffer chemotaxis assay 26117562
C-C chemokine receptor type 9 IC50 = 539.0 nM 6.27 Antagonist activity at CCR9 receptor (unknown origin) by serum chemotaxis assay 26117562

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
26987013 10.1021/acs.jmedchem.5b01840 Mus musculus 5
26117562 10.1016/j.bmcl.2015.06.046 Mus musculus 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5

Data from ChEMBL 36 via Core Engine