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Compound Detail

CHEMBL1915540

ADRIFORANT
🧪 Phase II
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🧪 Phase II
CN[C@@H]1CCN(c2cc(NCC3CC3)nc(N)n2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1915540
Name ADRIFORANT
Phase Phase II
Structure Type MOL
InChI Key ISBHYKVAFKTATD-SNVBAGLBSA-N

Known Names

Adriforant NVP-ZPL389-NX Pf-03893787 PF-3893787 ZPL-389 ZPL-389-NX ZPL-3893787 ZPL389-NX
7
Targets
25
Activities
3
Assay Types
8
PK Parameters
16
Publications
8
Known Names
4
Indications
1
Mechanisms

Molecular Properties

262.4
MW (Da)
0.68
ALogP
6
HBA
3
HBD
79.1
PSA (Ų)
0.72
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -forant
USAN Year 2020

Extended Properties

Molecular Formula C13H22N6
MW 262.36
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -1.49

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Histamine H4 receptor antagonist ANTAGONIST Histamine H4 receptor ✓ ✓

Indications

Dermatitis, Atopic Psoriasis Asthma Dermatitis

Activity Summary

Ki 20 meas. best 8.81
IC50 4 meas. best 9.19
Kd 1 meas. best 7.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H4 receptor
CHEMBL3759
 IC50 9.19 8.415 0.7 4
Histamine H4 receptor
CHEMBL3759
 Ki 8.81 8.41 1.6 6
Histamine H4 receptor
CHEMBL4468
 Ki 7.91 7.6933 12.3 3
Unchecked
CHEMBL612545
 Ki 7.81 6.8 15.5 4
Histamine H4 receptor
CHEMBL5657
 Ki 7.68 7.54 20.9 3
Histamine H4 receptor
CHEMBL3759
 Kd 7.6 7.6 25.1 1
Histamine H4 receptor
CHEMBL1255160
 Ki 6.91 6.91 123.0 2
Histamine H3 receptor
CHEMBL264
 Ki 6.73 6.73 186.2 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 5.46 5.46 3467.4 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.0 mL.min-1.kg-1 Canis lupus familiaris
CL 29.0 mL.min-1.kg-1 Rattus norvegicus
F 39.0 % Canis lupus familiaris
F 62.0 % Rattus norvegicus
T1/2 24.0 hr Canis lupus familiaris
T1/2 7.0 hr Rattus norvegicus
Vd 14.0 L.kg-1 Canis lupus familiaris
Vd 18.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H4 receptor IC50 = 0.65 nM 9.19 Antagonist activity at H4R in human eosinophils assessed as inhibition of histam... 21920751
Histamine H4 receptor IC50 = 1.3 nM 8.89 Antagonist activity at H4R in human eosinophils assessed as inhibition of histam... 21920751
Histamine H4 receptor Ki = 1.56 nM 8.81 Antagonist activity at full length human H4R expressed in HEK293 cells assessed ... 21920751
Histamine H4 receptor Ki = 2.4 nM 8.62 Displacement of [3H]-histamine from full length human H4R expressed in HEK293 ce... 21920751
Histamine H4 receptor Ki = 2.4 nM 8.62 Binding affinity to human histamine H4 receptor 25993395
Histamine H4 receptor IC50 = 4.9 nM 8.31 Antagonist activity at H4R in human eosinophils assessed as inhibition of histam... 21920751
Histamine H4 receptor Ki = 6.166 nM 8.21 Displacement of [3H]-histamine from human H4R expressed in HEK293T cells 21920751
Histamine H4 receptor Ki = 6.166 nM 8.21 Displacement of [3H]histamine from human histamine H4 receptor expressed in HEK2... 25993395
Histamine H4 receptor Ki = 10.23 nM 7.99 Displacement of [3H]histamine from human histamine H4 receptor expressed in HEK ... 23558237
Histamine H4 receptor Ki = 12.3 nM 7.91 Displacement of [3H]histamine from rat histamine H4 receptor expressed in HEK293... 25993395
Histamine H4 receptor Ki = 12.3 nM 7.91 Displacement of [3H]-histamine from rat H4R expressed in HEK293T cells 21920751
Unchecked Ki = 15.49 nM 7.81 Displacement of [3H]-histamine from macaque H4R expressed in HEK293T cells 21920751
Unchecked Ki = 15.49 nM 7.81 Displacement of [3H]histamine from monkey histamine H4 receptor expressed in HEK... 25993395
Histamine H4 receptor Ki = 20.89 nM 7.68 Displacement of [3H]-histamine from mouse H4R expressed in HEK293T cells 21920751
Histamine H4 receptor Ki = 20.89 nM 7.68 Displacement of [3H]histamine from mouse histamine H4 receptor expressed in HEK2... 25993395
Histamine H4 receptor Kd = 25.12 nM 7.6 Displacement of [3H]histamine from human histamine H4 receptor expressed in HEK ... 23558237
Histamine H4 receptor IC50 = 53.7 nM 7.27 Antagonist activity at human histamine H4 receptor expressed in HEK cells assess... 23558237
Histamine H4 receptor Ki = 54.95 nM 7.26 Binding affinity to rat histamine H4 receptor 23558237
Histamine H4 receptor Ki = 54.95 nM 7.26 Binding affinity to mouse histamine H4 receptor 23558237
Histamine H4 receptor Ki = 123.03 nM 6.91 Displacement of [3H]-histamine from guinea pig H4R expressed in HEK293T cells 21920751

Literature References

PubMed DOI Target Context # Activities
21920751 10.1016/j.bmcl.2011.07.125 Histamine H4 receptor 14
23558237 10.1016/j.bmcl.2013.02.091 Histamine H4 receptor 6
25993395 10.1021/acs.jmedchem.5b00516 Histamine H4 receptor 5
21920751 10.1016/j.bmcl.2011.07.125 Canis familiaris 4
21920751 10.1016/j.bmcl.2011.07.125 Rattus norvegicus 4
21920751 10.1016/j.bmcl.2011.07.125 Unchecked 4
21920751 10.1016/j.bmcl.2011.07.125 Plasma 3
21920751 10.1016/j.bmcl.2011.07.125 Nucleic Acid 3
23558237 10.1016/j.bmcl.2013.02.091 Unchecked 3
21920751 10.1016/j.bmcl.2011.07.125 Liver microsomes 2
25993395 10.1021/acs.jmedchem.5b00516 Unchecked 2
21920751 10.1016/j.bmcl.2011.07.125 No relevant target 1
23558237 10.1016/j.bmcl.2013.02.091 Histamine H2 receptor 1
23558237 10.1016/j.bmcl.2013.02.091 Histamine H1 receptor 1
23558237 10.1016/j.bmcl.2013.02.091 Voltage-gated inwardly rectifying potassium channel KCNH2 1
23558237 10.1016/j.bmcl.2013.02.091 Histamine H3 receptor 1

Data from ChEMBL 36 via Core Engine