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Compound Detail

CHEMBL218166

BIFEPRUNOX
🧪 Phase III
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🧪 Phase III
O=c1[nH]c2cccc(N3CCN(Cc4cccc(-c5ccccc5)c4)CC3)c2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL218166
Name BIFEPRUNOX
Phase Phase III
Structure Type MOL
InChI Key CYGODHVAJQTCBG-UHFFFAOYSA-N

Known Names

Bifeprunox
5
Targets
14
Activities
3
Assay Types
1
PK Parameters
15
Publications
1
Known Names
6
Indications
2
Mechanisms

Molecular Properties

385.5
MW (Da)
4.11
ALogP
4
HBA
1
HBD
52.5
PSA (Ų)
0.57
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 2005

Extended Properties

Molecular Formula C24H23N3O2
MW 385.47
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -0.98

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin 1a (5-HT1a) receptor partial agonist PARTIAL AGONIST 5-hydroxytryptamine receptor 1A ✓ ✓
Dopamine D2 receptor partial agonist PARTIAL AGONIST D(2) dopamine receptor ✓ ✓

Indications

Alzheimer Disease Bipolar Disorder Bipolar Disorder Depressive Disorder Schizophrenia Psychotic Disorders

Activity Summary

Ki 12 meas. best 10.4
EC50 1 meas. best 6.49
IC50 1 meas. best 8.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL217
 Ki 10.4 9.1743 0.0 7
D(2) dopamine receptor
CHEMBL339
 Ki 8.81 8.81 1.5 1
D(2) dopamine receptor
CHEMBL217
 IC50 8.54 8.54 2.9 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 8.03 8.03 9.3 2
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 7.19 7.19 64.6 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 EC50 6.49 6.49 323.6 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 5.48 5.48 3311.3 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.433 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor Ki = 0.04 nM 10.4 Displacement of [3H]spiperone from human dopamine D2 receptor at high affinity s... 20155917
D(2) dopamine receptor Ki = 0.1 nM 10.0 Displacement of [3H]spiperone from human dopamine D2 receptor at low affinity st... 20155917
D(2) dopamine receptor Ki = 0.6 nM 9.22 Displacement of [3H]raclopride from human D2 dopamine receptor expressed in CHO ... 23237836
D(2) dopamine receptor Ki = 1.549 nM 8.81 Displacement of [3H]YM-09151-2 from rat striatum D2 receptor 17300168
D(2) dopamine receptor Ki = 2.2 nM 8.66 Binding affinity for dopamine receptor D2 determined using [3H]spiperone 11527728
D(2) dopamine receptor Ki = 2.2 nM 8.66 Agonist activity at dopamine D2 receptor 20153652
D(2) dopamine receptor Ki = 2.3 nM 8.64 Displacement of [3H]nemonapride from dopamine D2L receptor (unknown origin) expr... 24878269
D(2) dopamine receptor Ki = 2.291 nM 8.64 Displacement of [3H]nemonapride from dopamine D2L receptor (unknown origin) expr... 24878269
D(2) dopamine receptor IC50 = 2.9 nM 8.54 Antagonist activity at human D2 dopamine receptor expressed in CHO cell membrane... 23237836
5-hydroxytryptamine receptor 1A Ki = 9.3 nM 8.03 Binding affinity for 5-hydroxytryptamine 1A receptor determined using [3H]8-OH-D... 11527728
5-hydroxytryptamine receptor 1A Ki = 9.3 nM 8.03 Agonist activity at 5HT1A receptor 20153652
5-hydroxytryptamine receptor 1A Ki = 64.57 nM 7.19 Displacement of [3H]OH-DPAT from rat cortex 5HT1A receptor 17300168
5-hydroxytryptamine receptor 1A EC50 = 323.59 nM 6.49 Agonist activity at human 5HT1A receptor in HeLa cells assessed as stimulation o... 17300168
5-hydroxytryptamine receptor 2A Ki = 3311.31 nM 5.48 Displacement of [3H]ketanserin from rat cortex 5HT2A receptor 17300168

Literature References

PubMed DOI Target Context # Activities
28408223 10.1016/j.bmcl.2017.03.084 D(2) dopamine receptor 7
20155917 10.1021/jm901689v D(2) dopamine receptor 4
17300168 10.1021/jm061180b 5-hydroxytryptamine receptor 1A 3
20155917 10.1021/jm901689v Rattus norvegicus 3
23237836 10.1016/j.bmcl.2012.11.023 D(2) dopamine receptor 3
24878269 10.1021/jm5003759 D(2) dopamine receptor 3
11527728 10.1016/s0960-894x(01)00425-5 Rattus norvegicus 2
- 10.6019/CHEMBL4888484 Plasmodium falciparum 2
11527728 10.1016/s0960-894x(01)00425-5 D(2) dopamine receptor 1
11527728 10.1016/s0960-894x(01)00425-5 5-hydroxytryptamine receptor 1A 1
11527728 10.1016/s0960-894x(01)00425-5 Mus musculus 1
17300168 10.1021/jm061180b 5-hydroxytryptamine receptor 2A 1
17300168 10.1021/jm061180b D(2) dopamine receptor 1
20153652 10.1016/j.bmc.2010.01.040 D(2) dopamine receptor 1
20153652 10.1016/j.bmc.2010.01.040 5-hydroxytryptamine receptor 1A 1

Data from ChEMBL 36 via Core Engine