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Compound Detail

CHEMBL243712

AMISULPRIDE
💊 Approved Drug
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💊 Approved Drug
CCN1CCCC1CNC(=O)c1cc(S(=O)(=O)CC)c(N)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL243712
Name AMISULPRIDE
Phase Approved
Structure Type MOL
InChI Key NTJOBXMMWNYJFB-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Aminosultopride Amisulprida Amisulpride APD-421 APD421 Barhemsys DAN-2163 Deniban NSC-760085 Socian Solian Solian 100 +4 more
6
Targets
16
Activities
2
Assay Types
4
PK Parameters
20
Publications
16
Known Names
13
Indications
2
Mechanisms

Molecular Properties

369.5
MW (Da)
1.29
ALogP
6
HBA
2
HBD
101.7
PSA (Ų)
0.70
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1986
Availability Prescription
Chirality Racemic

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -pride

Extended Properties

Molecular Formula C17H27N3O4S
MW 369.49
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness -1.38

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin (5-HT) receptor antagonist ANTAGONIST Serotonin (5-HT) receptor ✓ ✓
Dopamine receptors; D2 & D3 antagonist ANTAGONIST Dopamine receptors; D2 & D3 ✓ ✓

Indications

Postoperative Nausea and Vomiting Postoperative Nausea and Vomiting Psychotic Disorders Anxiety Dementia Depressive Disorder Schizophrenia Bipolar Disorder Nausea Depressive Disorder, Major Obsessive-Compulsive Disorder Renal Insufficiency, Chronic Anorexia Nervosa

ATC Classification

N05AL05
amisulpride
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

Ki 10 meas. best 8.52
IC50 6 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL217
 IC50 8.82 8.365 1.5 6
D(2) dopamine receptor
CHEMBL217
 Ki 8.52 8.21 3.0 2
D(3) dopamine receptor
CHEMBL234
 Ki 8.46 8.43 3.5 2
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 7.94 7.77 11.5 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 7.89 7.195 13.0 2
Adrenergic receptor alpha-2
CHEMBL2093864
 Ki 6.9 6.9 125.9 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.2 6.2 631.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.8 mL.min-1.kg-1 Homo sapiens
CL 3.4 mL.min-1.kg-1 Homo sapiens
CL 7.8 mL.min-1.kg-1 Homo sapiens
Fu 0.84 - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor IC50 = 1.5 nM 8.82 Dopamine D2 Receptors (Cell-Based Assay): The ability of Compound 102 to bind do... -
D(2) dopamine receptor IC50 = 1.5 nM 8.82 Binding of Compound 102 to Dopamine D2 Receptors (Cell-Based Assay): The ability... -
D(2) dopamine receptor IC50 = 3.04 nM 8.52 Antagonistic activity at D2 receptor (unknown origin) expressed in CHOK1 cells c... 27487565
D(2) dopamine receptor Ki = 3.0 nM 8.52 Displacement of [3H]N-methyl-spiperone from D2R (unknown origin) assessed as inh... 34311086
D(3) dopamine receptor Ki = 3.5 nM 8.46 Displacement of [3H]N-methyl-spiperone from D3R (unknown origin) assessed as inh... 34311086
D(3) dopamine receptor Ki = 3.981 nM 8.4 Displacement of [3H]spiperone from human dopamine D3 receptor expressed in CHO c... 17880057
D(2) dopamine receptor IC50 = 8.5 nM 8.07 Binding of Compound 102 to Dopamine D2 Receptors (Membrane Preparation): The abi... -
D(2) dopamine receptor IC50 = 8.5 nM 8.07 Binding of Compound 102 to Dopamine D2 Receptors (Membrane Preparation): The abi... -
5-hydroxytryptamine receptor 7 Ki = 11.5 nM 7.94 Displacement of [3H]LSD from 5-HT7R (unknown origin) assessed as inhibition cons... 34311086
D(2) dopamine receptor Ki = 12.59 nM 7.9 Displacement of [3H]spiperone from human dopamine D2 receptor short form express... 17880057
D(2) dopamine receptor IC50 = 12.98 nM 7.89 Antagonist activity at DRD2 (unknown origin) 39082833
5-hydroxytryptamine receptor 2B Ki = 13.0 nM 7.89 Displacement of [3H]-LSD from human 5-HT2B receptor assessed as inhibition const... 37584406
5-hydroxytryptamine receptor 7 Ki = 25.12 nM 7.6 Displacement of [3H]LSD from human 5HT7 receptor expressed in CHO cells 17880057
Adrenergic receptor alpha-2 Ki = 125.89 nM 6.9 Displacement of [3H]RX 821002 from adrenergic alpha-2 receptor in rat cerebral c... 17880057
5-hydroxytryptamine receptor 2B Ki = 316.23 nM 6.5 Displacement of [3H]DOI from 5HT2B receptor expressed in CHO cells 17880057
5-hydroxytryptamine receptor 2A Ki = 630.96 nM 6.2 Displacement of [3H]ketanserin from human 5HT2A receptor expressed in CHO cells 17880057

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 70
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
32088124 10.1016/j.bmc.2020.115372 Histone-lysine N-methyltransferase SETD7 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
24249037 10.1007/s11095-013-1232-z No relevant target 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
27487565 10.1016/j.ejmech.2016.07.038 D(2) dopamine receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2

Data from ChEMBL 36 via Core Engine