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Compound Detail

CHEMBL14638

CIPROXIFAN
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O=C(c1ccc(OCCCc2c[nH]cn2)cc1)C1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL14638
Name CIPROXIFAN
Phase Preclinical
Structure Type MOL
InChI Key ACQBHJXEAYTHCY-UHFFFAOYSA-N
10
Targets
45
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

270.3
MW (Da)
3.01
ALogP
3
HBA
1
HBD
55.0
PSA (Ų)
0.62
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H18N2O2
MW 270.33
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.62

Activity Summary

Ki 35 meas. best 9.31
IC50 10 meas. best 5.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H3 receptor
CHEMBL4124
 Ki 9.31 9.1763 0.5 8
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 7.37 7.37 42.7 1
Histamine H3 receptor
CHEMBL264
 Ki 7.34 7.21 46.0 19
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 7.2 7.2 63.1 1
Unchecked
CHEMBL612545
 Ki 6.52 5.3433 302.0 3
Histamine H4 receptor
CHEMBL3759
 Ki 6.21 6.05 612.0 3
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 5.72 5.6933 1900.0 3
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 4.96 4.9467 11000.0 3
Cholinesterase
CHEMBL1914
 IC50 4.11 4.11 77300.0 2
Acetylcholinesterase
CHEMBL220
 IC50 4.07 4.07 86100.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 14.83 mL.min-1.kg-1 Rattus norvegicus
F 51.0 % Rattus norvegicus
T1/2 1.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H3 receptor Ki = 0.49 nM 9.31 In vitro inhibitory activity against Histamine H3 receptor for K+ evoked depolar... 11055360
Histamine H3 receptor Ki = 0.49 nM 9.31 In vitro binding affinity against rat histamine H3 receptor 15115409
Histamine H3 receptor Ki = 0.49 nM 9.31 Histamine H3 receptor antagonist activity in an assay with K+ evoked depolarizat... 10966752
Histamine H3 receptor Ki = 0.5129 nM 9.29 In vitro binding affinity was determined as displacement of [3H]N-R-methylhistam... 15634000
Histamine H3 receptor Ki = 0.51 nM 9.29 In vitro binding affinity was determined as displacement of [3H]N-R-methylhistam... 15634000
Histamine H3 receptor Ki = 0.5129 nM 9.29 Displacement of [3H]NAMH from rat full length histamine H3 receptor expressed in... 18683917
Histamine H3 receptor Ki = 0.631 nM 9.2 Displacement of [3H]NAMH from histamine H3 receptor in rat cortex 18683917
Histamine H3 receptor Ki = 3.9 nM 8.41 Inhibition of [125I]iodoproxyfan from rat histamine H3 receptor expressed in CHO... 11294398
Alpha-2A adrenergic receptor Ki = 42.66 nM 7.37 Displacement of [3H]rauwolscine from human adrenergic alpha 2C10 receptor expres... 18683917
Histamine H3 receptor Ki = 46.0 nM 7.34 Displacement of [3H]Nalpha-methylhistamine from human recombinant histamine H3 r... 24900647
Histamine H3 receptor Ki = 46.0 nM 7.34 Inhibition of human histamine H3 receptor 31401465
Histamine H3 receptor Ki = 46.0 nM 7.34 Displacement of [3H]-N-alpha-methylhistamine from human H3R expressed in HEK293 ... 30744931
Histamine H3 receptor Ki = 46.0 nM 7.34 Inhibition of [125I]iodoproxyfan binding to human histamine H3 receptor of CHO-K... 11294398
Histamine H3 receptor Ki = 46.0 nM 7.34 Displacement of [125I]iodoproxyfan from human histamine H3 receptor expressing C... 12672253
Histamine H3 receptor Ki = 46.0 nM 7.34 Displacement of [3H]iodoproxyfan from human histamine H3 receptor expressed in C... 19846299
Histamine H3 receptor Ki = 46.0 nM 7.34 Displacement of [125I]iodoproxyfan from human full-length histamine H3 receptor ... 21498080
Histamine H3 receptor Ki = 46.0 nM 7.34 Binding affinity to human H3R 29477889
Histamine H3 receptor Ki = 48.9 nM 7.31 Displacement of [3H]UR-PI294 from human SP-FLAG-tagged H3R expressed in HEK293T ... 33261900
Histamine H3 receptor Ki = 63.1 nM 7.2 Antagonist activity at human histamine H3 receptor expressed in CHOK1 cells asse... 24161834
Histamine H3 receptor Ki = 63.0 nM 7.2 Binding affinity to human H3 receptor 22313227

Literature References

PubMed DOI Target Context # Activities
18683917 10.1021/jm8003625 Histamine H3 receptor 11
15634000 10.1021/jm040118g ADMET 5
15634000 10.1021/jm040118g Histamine H3 receptor 5
33261900 10.1016/j.ejmech.2020.113041 Histamine H3 receptor 4
18683917 10.1021/jm8003625 Unchecked 3
15634000 10.1021/jm040118g Rattus norvegicus 3
11294398 10.1016/s0960-894x(01)00090-7 Histamine H3 receptor 3
11055360 10.1016/s0960-894x(00)00473-x Histamine H3 receptor 2
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A2a 2
12672253 10.1021/jm021084k Histamine H3 receptor 2
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A3 2
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A1 2
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A2b 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
10966752 10.1021/jm000971p Mus musculus 1
15634025 10.1021/jm040873u Histamine H3 receptor 1
10966752 10.1021/jm000971p Histamine H3 receptor 1
15139761 10.1021/jm031028z Histamine H3 receptor 1
17918921 10.1021/jm0705051 Rattus norvegicus 1
18683917 10.1021/jm8003625 Histamine H4 receptor 1

Data from ChEMBL 36 via Core Engine