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Compound Detail

CHEMBL216981

NAVARIXIN ANHYDROUS
🧪 Phase II
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🧪 Phase II
CC[C@@H](Nc1c(Nc2cccc(C(=O)N(C)C)c2O)c(=O)c1=O)c1ccc(C)o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL216981
Name NAVARIXIN ANHYDROUS
Phase Phase II
Structure Type MOL
InChI Key RXIUEIPPLAFSDF-CYBMUJFWSA-N

Known Names

MK-7123 MK7123 Navarixin (anhydrous) Navarixin anhydrous Navarixina Navarixine SCH-527123 SCH527123
6
Targets
27
Activities
3
Assay Types
12
PK Parameters
20
Publications
8
Known Names
2
Mechanisms

Molecular Properties

397.4
MW (Da)
2.90
ALogP
7
HBA
3
HBD
111.9
PSA (Ų)
0.42
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -rixin
USAN Year 2010

Extended Properties

Molecular Formula C21H23N3O5
MW 397.43
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.93

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Interleukin-8 receptor B antagonist ANTAGONIST C-X-C chemokine receptor type 2 ✓ ✓
Interleukin-8 receptor A antagonist ANTAGONIST C-X-C chemokine receptor type 1 ✓ ✓

Activity Summary

IC50 18 meas. best 10.31
Ki 7 meas. best 9.19
Kd 2 meas. best 10.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-X-C chemokine receptor type 2
CHEMBL2434
 IC50 10.31 8.1063 0.0 8
C-X-C chemokine receptor type 2
CHEMBL2434
 Kd 10.31 10.305 0.0 2
C-X-C chemokine receptor type 2
CHEMBL2434
 Ki 9.19 8.5475 0.6 4
C-X-C chemokine receptor type 1
CHEMBL4029
 IC50 8.41 7.2483 3.9 6
C-X-C chemokine receptor type 2
CHEMBL4105830
 IC50 8.09 8.09 8.1 1
Interleukin-8 receptors, CXCR1/CXCR2
CHEMBL2096909
 IC50 7.8 7.8 16.0 1
C-X-C chemokine receptor type 1
CHEMBL4029
 Ki 7.75 7.7033 18.0 3
C-C chemokine receptor type 7
CHEMBL4594
 IC50 5.33 5.33 4680.0 1
Caco-2
CHEMBL614058
 IC50 4.73 4.73 18780.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 19474.07 ng.hr.mL-1 Rattus norvegicus
AUC 8743.46 ng.hr.mL-1 Rattus norvegicus
AUC 794.86 ng.hr.mL-1 Macaca mulatta
AUC 19474.07 ng.hr.mL-1 Rattus norvegicus
CL 75.93 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 mL.min-1.g-1 Homo sapiens
F 33.0 % Rattus norvegicus
F 18.0 % Macaca mulatta
MRT 3.4 hr Rattus norvegicus
MRT 2.0 hr Macaca mulatta
T1/2 7.8 hr Rattus norvegicus
T1/2 23.3 hr Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-X-C chemokine receptor type 2 IC50 = 0.049 nM 10.31 Binding affinity to CXCR2 22931505
C-X-C chemokine receptor type 2 Kd = 0.049 nM 10.31 Displacement of [3H]Sch527123 from human CXCR2 assessed as dissociation constant... 37523859
C-X-C chemokine receptor type 2 Kd = 0.05012 nM 10.3 Binding affinity to CXCL2 (unknown origin) 37523859
C-X-C chemokine receptor type 2 Ki = 0.6457 nM 9.19 Binding affinity to NanoLuc fused Snap CXCR2 (unknown origin) expressed in HEK29... 37523859
C-X-C chemokine receptor type 2 IC50 = 2.6 nM 8.59 Antagonist activity at CXCR2 (unknown origin) 34355177
C-X-C chemokine receptor type 2 IC50 = 2.6 nM 8.59 Displacement of [125I]hCXCL8 from human CXCR2 receptor expressed in BaF3 cells 17181143
C-X-C chemokine receptor type 2 IC50 = 2.884 nM 8.54 Inhibition of CXCR2 (unknown origin) expressed in HEK293 coexpressing snap-CXCR2... 37523859
C-X-C chemokine receptor type 1 IC50 = 3.9 nM 8.41 Binding affinity to CXCR1 22931505
C-X-C chemokine receptor type 2 Ki = 4.0 nM 8.4 Binding affinity to CXCR2 19196511
C-X-C chemokine receptor type 2 IC50 = 5.0 nM 8.3 Antagonist activity at CXCR2 in human CD4 cells by fluorescence based calcium mo... 36924670
C-X-C chemokine receptor type 2 Ki = 5.0 nM 8.3 Displacement of human [125I]IL-8 from human CXCR2 19525110
C-X-C chemokine receptor type 2 Ki = 5.0 nM 8.3 Displacement of [125I]IL8 from human CXCR2 expressed in CHO cells by SPA 17459706
C-X-C chemokine receptor type 2 IC50 = 8.1 nM 8.09 Antagonist activity at CXCR2 in C57 mouse whole blood assessed as inhibition of ... 29406702
C-X-C chemokine receptor type 2 IC50 = 10.0 nM 8.0 Antagonist activity in CXCR2 (unknown origin) expressed in human HEK293 cells co... 34055234
Interleukin-8 receptors, CXCR1/CXCR2 IC50 = 16.0 nM 7.8 Inhibition of CXCL8-induced human neutrophil chemotaxis 17181143
C-X-C chemokine receptor type 1 Ki = 18.0 nM 7.75 Displacement of [125I]IL8 from human CXCR1 expressed in CHO cells by SPA 17459706
C-X-C chemokine receptor type 1 Ki = 20.0 nM 7.7 Binding affinity to CXCR1 19196511
C-X-C chemokine receptor type 1 Ki = 21.88 nM 7.66 Binding affinity to NanoLuc fused Snap CXCR1 (unknown origin) expressed in HEK29... 37523859
C-X-C chemokine receptor type 1 IC50 = 36.0 nM 7.44 Antagonist activity at CXCR1 (unknown origin) 34355177
C-X-C chemokine receptor type 1 IC50 = 36.0 nM 7.44 Displacement of [125I]hCXCL8 from human CXCR1 receptor expressed in BaF3 cells 17181143

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3301361 ADMET 5
18304809 10.1016/j.bmcl.2008.02.010 Rattus norvegicus 4
37523859 10.1021/acs.jmedchem.3c00849 C-X-C chemokine receptor type 2 4
18304809 10.1016/j.bmcl.2008.02.010 Rhesus monkey 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
17181143 10.1021/jm0609622 C-X-C chemokine receptor type 2 3
29406702 10.1021/acs.jmedchem.7b01854 C-X-C chemokine receptor type 2 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
34055234 10.1021/acsmedchemlett.1c00113 A-375 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
31732253 10.1016/j.ejmech.2019.111853 A375-SM 2
17181143 10.1021/jm0609622 C-C chemokine receptor type 5 1
17181143 10.1021/jm0609622 fMet-Leu-Phe receptor 1
17181143 10.1021/jm0609622 C-X-C chemokine receptor type 3 1
17459706 10.1016/j.bmcl.2007.04.016 C-X-C chemokine receptor type 1 1
19196511 10.1016/j.bmcl.2009.01.033 C-X-C chemokine receptor type 2 1
19196511 10.1016/j.bmcl.2009.01.033 C-X-C chemokine receptor type 1 1
17181143 10.1021/jm0609622 Rattus norvegicus 1
37523859 10.1021/acs.jmedchem.3c00849 C-X-C chemokine receptor type 1 1

Data from ChEMBL 36 via Core Engine