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Compound Detail

CHEMBL260374

THIOPERAMIDE
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S=C(NC1CCCCC1)N1CCC(c2cnc[nH]2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL260374
Name THIOPERAMIDE
Phase Preclinical
Structure Type MOL
InChI Key QKDDJDBFONZGBW-UHFFFAOYSA-N
12
Targets
143
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

292.4
MW (Da)
2.80
ALogP
2
HBA
2
HBD
44.0
PSA (Ų)
0.82
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H24N4S
MW 292.45
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -1.16

Activity Summary

Ki 104 meas. best 8.81
EC50 16 meas. best 7.96
IC50 16 meas. best 8.71
Kd 7 meas. best 9.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H3 receptor
CHEMBL5076
 Kd 9.06 8.808 0.9 5
Histamine H3 receptor
CHEMBL4124
 Ki 8.81 8.3921 1.5 28
Histamine H3 receptor
CHEMBL264
 IC50 8.71 7.0711 2.0 9
Histamine H3 receptor
CHEMBL5076
 Ki 8.4 8.2267 4.0 3
Histamine H4 receptor
CHEMBL3759
 Ki 8.4 6.9434 4.0 29
Histamine H3 receptor
CHEMBL3263
 Ki 8.32 8.32 4.8 1
Histamine H3 receptor
CHEMBL264
 Ki 8.19 7.2766 6.5 35
Histamine H3 receptor
CHEMBL3263
 EC50 7.96 7.96 11.0 1
Histamine H4 receptor
CHEMBL3759
 IC50 7.72 6.478 19.0 5
Histamine H4 receptor
CHEMBL5657
 EC50 7.55 7.035 28.2 2
Histamine H3 receptor
CHEMBL264
 EC50 7.47 7.178 34.0 5
Histamine H3 receptor
CHEMBL264
 Kd 7.36 7.28 43.6 2
Histamine H4 receptor
CHEMBL4468
 Ki 7.3 7.3 50.1 1
Histamine H4 receptor
CHEMBL5657
 Ki 7.18 7.14 66.1 2
Histamine H4 receptor
CHEMBL3759
 EC50 7.15 6.9588 70.8 8
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 6.9 6.9 125.9 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 6.46 6.46 346.7 1
Cholesterol 24-hydroxylase
CHEMBL4523510
 IC50 6.37 6.37 430.0 1
Unchecked
CHEMBL612545
 Ki 5.64 5.28 2290.9 3
Cytochrome P450 3A4
CHEMBL340
 IC50 5.21 5.21 6095.4 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H3 receptor Kd = 0.871 nM 9.06 Antagonist activity at histamine H3 receptor in guinea pig jejunum assessed as e... 18990469
Histamine H3 receptor Kd = 1.047 nM 8.98 Antagonist activity at histamine H3 receptor in guinea pig jejunum assessed as e... 30881612
Histamine H3 receptor Kd = 1.259 nM 8.9 Displacement of [3H]Nalpha-methylhistamine from histamine H3 receptors in homoge... 11356102
Histamine H3 receptor Ki = 1.54 nM 8.81 Antagonistic activity was evaluated against histamine H3 receptor using [3H]- N-... 9871722
Histamine H3 receptor IC50 = 1.96 nM 8.71 Inhibition of recombinant human histamine H3 receptor stably expressed in HEK293... 37418295
Histamine H3 receptor Ki = 1.995 nM 8.7 In vitro antagonistic activity against histamine H3 receptor on rat cerebral cor... 8632428
Histamine H3 receptor Ki = 1.995 nM 8.7 Binding affinity against H3 receptor in rat cerebral cortex membranes was evalua... -
Histamine H3 receptor Ki = 2.1 nM 8.68 Displacement of [3H]-(R)alpha-MeHA from rat brain H3 receptor 29681486
Histamine H3 receptor Kd = 2.188 nM 8.66 Antagonist activity at histamine H3 receptor in Cavia porcellus (guinea pig) ile... -
Histamine H3 receptor Ki = 2.65 nM 8.58 Inhibition of rat Histamine H3 receptor using [3H]N-alpha-methyl histamine 12723960
Histamine H3 receptor Ki = 3.63 nM 8.44 In vitro binding affinity was determined as displacement of [3H]N-R-methylhistam... 15634000
Histamine H3 receptor Ki = 3.631 nM 8.44 In vitro binding affinity was determined as displacement of [3H]N-R-methylhistam... 15634000
Histamine H3 receptor Kd = 3.631 nM 8.44 Antagonist activity at histamine H3 receptor in guinea pig ileum assessed as inh... 18683917
Histamine H3 receptor Ki = 3.631 nM 8.44 Displacement of [3H]NAMH from rat full length histamine H3 receptor expressed in... 18683917
Histamine H3 receptor Ki = 4.0 nM 8.4 In vitro inhibitory activity against Histamine H3 receptor for K+ evoked depolar... 11055360
Histamine H3 receptor Ki = 4.0 nM 8.4 In vitro antagonistic activity against Histamine H3 receptor on Synaptosomes of ... 8676353
Histamine H3 receptor Ki = 3.981 nM 8.4 In vitro antagonistic activity against histamine H3-receptor in an assay with K+... -
Histamine H3 receptor Ki = 4.0 nM 8.4 Rat Histamine H3 receptor antagonism determined by [K+] - evoked depolarization-... 8809168
Histamine H3 receptor Ki = 4.0 nM 8.4 Histamine H3 receptor antagonist activity in an assay with K+ evoked depolarizat... 10966752
Histamine H3 receptor Ki = 3.981 nM 8.4 Antagonistic activity for Histamine H3 receptor on electrically evoked guinea-pi... -

Literature References

PubMed DOI Target Context # Activities
32420741 10.1021/acs.jmedchem.0c00160 Histamine H4 receptor 15
18683917 10.1021/jm8003625 Histamine H3 receptor 11
27007611 10.1021/acs.jmedchem.6b00120 Histamine H4 receptor 7
1967317 10.1021/jm00163a001 Rattus norvegicus 6
16942032 10.1021/jm0603318 Histamine H3 receptor 5
28888822 10.1016/j.bmcl.2017.08.060 Histamine H3 receptor 5
15634000 10.1021/jm040118g Histamine H3 receptor 5
16942032 10.1021/jm0603318 Histamine H4 receptor 5
32420741 10.1021/acs.jmedchem.0c00160 Histamine H3 receptor 5
- 10.1016/0960-894X(96)00122-9 Rattus norvegicus 4
19773175 10.1016/j.bmc.2009.08.059 Histamine H4 receptor 4
22153663 10.1016/j.bmcl.2011.10.104 Histamine H4 receptor 3
19791743 10.1021/jm900526h Histamine H4 receptor 3
15634000 10.1021/jm040118g Rattus norvegicus 3
19553110 10.1016/j.bmcl.2009.06.025 Histamine H3 receptor 3
27007611 10.1021/acs.jmedchem.6b00120 Histamine H2 receptor 3
11294398 10.1016/s0960-894x(01)00090-7 Histamine H3 receptor 3
30881612 10.1039/C8MD00527C Histamine H3 receptor 3
18683917 10.1021/jm8003625 Unchecked 3
8632428 10.1021/jm9504767 Histamine H3 receptor 3

Data from ChEMBL 36 via Core Engine