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Compound Detail

CHEMBL22242

REMOXIPRIDE
💊 Approved Drug
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💊 Approved Drug
CCN1CCC[C@H]1CNC(=O)c1c(OC)ccc(Br)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22242
Name REMOXIPRIDE
Phase Approved
Structure Type MOL
InChI Key GUJRSXAPGDDABA-NSHDSACASA-N
Therapeutic ✓ Yes

Known Names

A 33547 A-33547 A-33547.HCL.H20 FLA 731 FLA 731 FREE BASE FLA-731 FREE BASE FLA-731(-) Remoxiprida Remoxipride
8
Targets
12
Activities
3
Assay Types
13
PK Parameters
20
Publications
9
Known Names
1
Indications
1
Mechanisms

Molecular Properties

371.3
MW (Da)
2.68
ALogP
4
HBA
1
HBD
50.8
PSA (Ų)
0.84
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Stem -pride
USAN Year 1985

Extended Properties

Molecular Formula C16H23BrN2O3
MW 371.28
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness -0.68

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine D2 receptor antagonist ANTAGONIST D(2) dopamine receptor ✓ ✓

Indications

Psychotic Disorders

ATC Classification

N05AL04
remoxipride
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Withdrawn
hematological toxicity
Aplastic anemia
Country: Worldwide   Year: 1993
Withdrawn
hematological toxicity
aplastic anaemia
Country: Worldwide   Year: 1993

Activity Summary

IC50 7 meas. best 8.92
Ki 4 meas. best 7.26
Kd 1 meas. best 5.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL217
 IC50 8.92 7.49 1.2 2
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 7.26 7.26 55.0 1
D(2) dopamine receptor
CHEMBL5456
 Ki 6.06 6.06 873.0 1
D(2) dopamine receptor
CHEMBL339
 IC50 5.85 5.8167 1400.0 3
Dopamine receptor
CHEMBL2093868
 IC50 5.8 5.8 1570.0 1
D(4) dopamine receptor
CHEMBL219
 IC50 5.41 5.41 3872.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 5.41 5.41 3872.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Kd 5.4 5.4 3981.1 1
D(3) dopamine receptor
CHEMBL2304406
 Ki 5.34 5.34 4603.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 170.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 4.9 mL.min-1.kg-1 Canis lupus familiaris
CL 11.8 mL.min-1.kg-1 Macaca
Fu 0.28 - Homo sapiens
Fu 0.16 - Homo sapiens
Fu 0.16 - Homo sapiens
MRT 6.4 hr Homo sapiens
T1/2 5.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor IC50 = 1.202 nM 8.92 Antagonist activity at dopamine D2 receptor 20728966
Sigma non-opioid intracellular receptor 1 Ki = 55.0 nM 7.26 Binding affinity against the sigma receptor from guinea pig brain using the radi... -
D(2) dopamine receptor IC50 = 880.0 nM 6.06 Binding affinity to dopamine receptor D2 cloned from human, using [3H]- YM09151 ... 11052797
D(2) dopamine receptor Ki = 873.0 nM 6.06 Displacement of [3H]-YM 09151 from african green monkey Dopamine receptor D2 8523409
D(2) dopamine receptor IC50 = 1400.0 nM 5.85 Binding affinity against the Dopamine receptor D2 in rat striatnrn by using [3H]... -
D(2) dopamine receptor IC50 = 1570.0 nM 5.8 In vitro binding affinity at Dopamine receptor D2 in rat by displacing [3H]- spi... 4040977
Dopamine receptor IC50 = 1570.0 nM 5.8 Antidopamine activity in vitro by ability to displace [3H]spiperone from rat bra... 3941414
D(2) dopamine receptor IC50 = 1570.0 nM 5.8 Tested in vitro for inhibition of [3H]spiperone binding to dopamine receptor D2 7901417
D(4) dopamine receptor IC50 = 3872.0 nM 5.41 Binding affinity to dopamine receptor D4 cloned from human, using [3H]- YM09151 ... 11052797
D(4) dopamine receptor Ki = 3872.0 nM 5.41 Displacement of [3H]-YM 09151 from human Dopamine receptor D4 8523409
5-hydroxytryptamine receptor 1A Kd = 3981.07 nM 5.4 Binding affinity to 5HT1A receptor 19754201
D(3) dopamine receptor Ki = 4603.0 nM 5.34 Displacement of [3H]-YM 09151 from african monkey Dopamine receptor D3 8523409

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
- 10.6019/CHEMBL4689842 HEK-293T 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
16621936 10.1124/dmd.105.006619 ADMET 8
- 10.6019/CHEMBL4689842 Fibroblast 7
8064801 10.1021/jm00043a013 Rattus norvegicus 7
- 10.6019/CHEMBL4689842 U2OS 7
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
3941414 10.1021/jm00151a010 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
11052797 10.1021/jm990562x Rattus norvegicus 2

Data from ChEMBL 36 via Core Engine