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Compound Detail

CHEMBL267044

LEVOSULPIRIDE
🧪 Phase II
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🧪 Phase II
CCN1CCC[C@H]1CNC(=O)c1cc(S(N)(=O)=O)ccc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267044
Name LEVOSULPIRIDE
Phase Phase II
Structure Type MOL
InChI Key BGRJTUBHPOOWDU-NSHDSACASA-N

Known Names

(-)-sulpiride L-sulpiride Lesuride Levobren Levopraid Levopride Levosulpirida Levosulpiride S-(-)-sulpiride Sulpiride l-form Sulpiride, (-)- Sulpiride, (s)-
9
Targets
27
Activities
2
Assay Types
0
PK Parameters
20
Publications
12
Known Names
3
Indications
2
Mechanisms

Molecular Properties

341.4
MW (Da)
0.56
ALogP
5
HBA
2
HBD
101.7
PSA (Ų)
0.79
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C15H23N3O4S
MW 341.43
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness -1.62

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine D2 receptor antagonist ANTAGONIST D(2) dopamine receptor ✓ ✓
Serotonin 4 (5-HT4) receptor agonist AGONIST 5-hydroxytryptamine receptor 4 ✓ ✓

Indications

Psychomotor Agitation Psychotic Disorders Dyspepsia

ATC Classification

N05AL07
levosulpiride
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

Ki 19 meas. best 8.16
IC50 8 meas. best 6.91

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL339
 Ki 8.16 7.642 6.9 5
D(3) dopamine receptor
CHEMBL234
 Ki 7.38 7.1667 42.0 3
D(2) dopamine receptor
CHEMBL217
 Ki 7.37 7.158 43.0 5
D(3) dopamine receptor
CHEMBL234
 IC50 6.91 6.91 123.0 1
D(2) dopamine receptor
CHEMBL217
 IC50 6.89 6.89 128.0 1
D(2) dopamine receptor
CHEMBL339
 IC50 6.77 6.6933 170.0 3
Dopamine receptor
CHEMBL2093868
 IC50 6.68 6.68 210.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 5.68 5.68 2100.0 2
Myeloperoxidase
CHEMBL2439
 IC50 5.12 5.12 7680.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 4.82 4.82 15000.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 4.57 4.57 27000.0 1
D(1A) dopamine receptor
CHEMBL2967
 Ki 4.3 4.3 50000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor Ki = 6.9 nM 8.16 Inhibition of [3H]spiperone binding to rat striatal membrane Dopamine receptor D... 1969484
D(2) dopamine receptor Ki = 20.6 nM 7.69 Binding affinity towards dopamine receptor D2 by displacing [3H]spiperone radiol... 1346653
D(2) dopamine receptor Ki = 29.0 nM 7.54 Binding affinity towards dopamine receptor D2 using as [3H]-spiperone radioligan... 1825115
D(2) dopamine receptor Ki = 39.0 nM 7.41 Ability to inhibit the [3H]spiperone binding to striatum Dopamine receptor D2 wa... 2889830
D(2) dopamine receptor Ki = 39.0 nM 7.41 Compound was evaluated for binding affinity towards DA D-2 receptor using radiol... 1535660
D(3) dopamine receptor Ki = 42.0 nM 7.38 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor Ki = 43.0 nM 7.37 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor Ki = 51.0 nM 7.29 Binding affinity towards human Dopamine receptor D2 (short) by [3H]-spiperone di... 10206547
D(2) dopamine receptor Ki = 51.0 nM 7.29 In vitro displacement of [3H]spiperone from the recombinant human dopamine recep... 10987445
D(3) dopamine receptor Ki = 88.0 nM 7.06 Binding affinity towards human dopamine D3 receptor by [3H]spiperone displacemen... 10206547
D(3) dopamine receptor Ki = 88.0 nM 7.06 In vitro displacement of [3H]spiperone from the cloned human dopamine receptor D... 10987445
D(2) dopamine receptor Ki = 120.0 nM 6.92 Binding affinity towards human Dopamine receptor D2 (long) by [3H]-spiperone dis... 10206547
D(2) dopamine receptor Ki = 120.0 nM 6.92 In vitro displacement of [3H]spiperone from the recombinant human dopamine recep... 10987445
D(3) dopamine receptor IC50 = 123.0 nM 6.91 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor IC50 = 128.0 nM 6.89 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor IC50 = 170.0 nM 6.77 Inhibitory concentration required for displacing radioligand [3H]SPI from DA D-2... 1535660
Dopamine receptor IC50 = 210.0 nM 6.68 Antidopamine activity in vitro by ability to displace [3H]spiperone from rat bra... 3941414
D(2) dopamine receptor IC50 = 210.0 nM 6.68 In vitro ability to inhibit the binding of [3H]spiperone to dopamine receptor D2... 1969484
D(2) dopamine receptor IC50 = 233.0 nM 6.63 Inhibitory concentration required for displacing radioligand [3H]SPI from DA D-2... 1535660
D(4) dopamine receptor Ki = 2100.0 nM 5.68 In vitro displacement of [3H]spiperone from the recombinant human dopamine recep... 10987445

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 143
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
1969484 10.1021/jm00166a012 Rattus norvegicus 4
3761301 10.1021/jm00160a003 Carbonic anhydrase 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 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
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
1535660 10.1021/jm00091a002 D(2) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
1969484 10.1021/jm00166a012 D(2) dopamine receptor 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
10987445 10.1016/s0960-894x(00)00405-4 D(2) dopamine receptor 2
9464359 10.1021/jm970217c Rattus norvegicus 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
1346653 10.1021/jm00081a018 Rattus norvegicus 2

Data from ChEMBL 36 via Core Engine