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Compound Detail

CHEMBL26

SULPIRIDE
🧪 Phase III
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🧪 Phase III
CCN1CCCC1CNC(=O)c1cc(S(N)(=O)=O)ccc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL26
Name SULPIRIDE
Phase Phase III
Structure Type MOL
InChI Key BGRJTUBHPOOWDU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Abilit Aiglonyl Coolspan Dobren Dogmatil Dogmatyl Dolmatil Guastil Meresa Mirbanil Misulvan N05AL01 +14 more
33
Targets
175
Activities
3
Assay Types
8
PK Parameters
20
Publications
26
Known Names
5
Indications
1
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 Racemic

Flags

Natural Product
USAN Year 1968

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 ✓ ✓

Indications

Psychotic Disorders Anxiety Dementia Depressive Disorder Schizophrenia

ATC Classification

N05AL01
sulpiride
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

Ki 154 meas. best 9.1
IC50 18 meas. best 7.99
Kd 3 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 6
CHEMBL3025
 Ki 9.1 9.1 0.8 3
D(2) dopamine receptor
CHEMBL339
 Kd 8.82 8.82 1.5 1
D(2) dopamine receptor
CHEMBL217
 Kd 8.55 8.55 2.8 1
Carbonic anhydrase 7
CHEMBL2326
 Ki 8.44 6.44 3.6 3
Carbonic anhydrase 12
CHEMBL3242
 Ki 8.41 8.41 3.9 3
D(2) dopamine receptor
CHEMBL339
 Ki 8.26 7.44 5.5 2
D(2) dopamine receptor
CHEMBL217
 Ki 8.12 7.555 7.6 4
D(3) dopamine receptor
CHEMBL234
 Ki 8.1 7.42 8.0 3
D(2) dopamine receptor
CHEMBL217
 IC50 7.99 7.3533 10.3 3
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 7.75 7.75 18.0 1
Unchecked
CHEMBL612545
 Ki 7.72 6.3322 19.0 37
AGAP002992-PA
CHEMBL3399914
 Ki 7.53 7.53 29.5 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.51 7.374 31.0 5
D(2) dopamine receptor
CHEMBL339
 IC50 7.48 7.0575 33.0 4
D(3) dopamine receptor
CHEMBL234
 Kd 7.4 7.4 39.8 1
Carbonic anhydrase 1
CHEMBL261
 IC50 7.4 6.66 40.0 2
Carbonic anhydrase 2
CHEMBL205
 Ki 7.4 7.4 40.0 38
Carbonic anhydrase 2
CHEMBL205
 IC50 7.4 7.4 40.0 1
D(3) dopamine receptor
CHEMBL234
 IC50 7.18 6.84 66.2 4
Carbonate dehydratase
CHEMBL3745586
 Ki 7.17 7.17 67.4 1
Carbonic anhydrase 15
CHEMBL5973
 Ki 7.14 7.14 73.0 1
Carbonic anhydrase
CHEMBL6185
 Ki 6.95 6.95 113.0 1
Carbonic anhydrase
CHEMBL5931
 Ki 6.91 6.91 124.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 6.76 6.76 174.0 1
Carbonic anhydrase
CHEMBL4211
 Ki 6.75 6.72 179.0 2
D(2) dopamine receptor
CHEMBL2703
 IC50 6.7 6.7 200.0 1
Delta carbonic anhydrase
CHEMBL3097982
 Ki 6.59 6.59 259.0 1
Carbonic anhydrase 2
CHEMBL6068
 Ki 6.58 6.58 266.0 1
Astrosclerin-3
CHEMBL1944499
 Ki 6.42 6.42 378.0 1
Carbonic anhydrase
CHEMBL1649055
 Ki 6.38 6.38 415.0 1
Alpha carbonic anhydrase
CHEMBL1075028
 Ki 6.37 6.37 430.0 2
Carbonic anhydrase 4
CHEMBL281
 IC50 6.21 6.21 620.0 1
Carbonic anhydrase
CHEMBL5337
 Ki 6.12 6.12 760.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 6.12 6.12 757.0 1
Carbonic anhydrase 2
CHEMBL1697676
 Ki 6.09 6.09 812.0 1
Carbonic anhydrase, alpha family
CHEMBL3621035
 Ki 6.06 6.06 873.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 5.92 5.6388 1200.0 32
Dopamine receptor
CHEMBL2093868
 Ki 5.8 5.8 1600.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 5.7 5.7 2019.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 5.68 5.68 2100.0 1
Beta-carbonic anhydrase 1
CHEMBL5631
 Ki 5.64 5.64 2300.0 1
Carbonic anhydrase 3
CHEMBL2885
 Ki 4.97 4.97 10600.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.83 mL.min-1.kg-1 Homo sapiens
CL 1.83 mL.min-1.kg-1 Homo sapiens
CL 0.1 mL.min-1.kg-1 Homo sapiens
F 49.0 % Homo sapiens
F 36.0 % Homo sapiens
Fu 0.72 - Homo sapiens
Fu 0.63 - Rattus norvegicus
Fu 0.24 - Sus scrofa

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 6 Ki = 0.8 nM 9.1 Inhibition of human recombinant CA6 by stopped-flow CO2 hydration assay 21208801
Carbonic anhydrase 6 Ki = 0.8 nM 9.1 Inhibition of human full length recombinant carbonic anhydrase 6 by stopped flow... 19193158
Carbonic anhydrase 6 Ki = 0.8 nM 9.1 Inhibition of full length human recombinant CA VI 17228881
D(2) dopamine receptor Kd = 1.5 nM 8.82 Affinity constant of compound was evaluated in rat striatum tissue preparation. 2966245
D(2) dopamine receptor Kd = 2.818 nM 8.55 Competitive antagonist activity at D2 long receptor (unknown origin) expressed i... 28186762
Carbonic anhydrase 7 Ki = 3.6 nM 8.44 Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins by... 24287559
Carbonic anhydrase 12 Ki = 3.9 nM 8.41 Inhibition of human transmembrane carbonic anhydrase 12 by stopped-flow CO2 hydr... 24513184
Carbonic anhydrase 12 Ki = 3.9 nM 8.41 Inhibition of human membrane bound carbonic anhydrase 12 preincubated for 15 min... 23965175
Carbonic anhydrase 12 Ki = 3.9 nM 8.41 Ki value against human carbonic anhydrase XII (hCA XII) 15686894
D(2) dopamine receptor Ki = 5.51 nM 8.26 Compound was tested for its ability to displace [3H]- spiperone from Dopamine re... 2522993
D(2) dopamine receptor Ki = 7.6 nM 8.12 Antagonist activity at dopamine D2 receptor (unknown origin) -
D(3) dopamine receptor Ki = 8.0 nM 8.1 Displacement of [125I]iodosulpiride from human Dopamine receptor D3 expressed in... 14521403
D(2) dopamine receptor Ki = 9.8 nM 8.01 Binding affinity to D2R (unknown origin) assessed as inhibition constant 34311086
D(2) dopamine receptor IC50 = 10.28 nM 7.99 Antagonist activity at human dopamine D2 receptor expressed in CHOp cells assess... 21495689
Carbonic anhydrase 5B, mitochondrial Ki = 18.0 nM 7.75 Inhibitory activity against human recombinant mitochondrial isozyme CA VB 16302824
Unchecked Ki = 19.0 nM 7.72 Inhibition of Brucella suis carbonic anhydrase I by spectrophotometry at pH 8.3 21251841
AGAP002992-PA Ki = 29.5 nM 7.53 Inhibition of Anopheles gambiae carbonic anhydrase pre-incubated for 15 mins by ... 25882523
Carbonic anhydrase 9 Ki = 31.0 nM 7.51 Inhibition of human recombinant carbonic anhydrase 9 by stopped-flow CO2 hydrase... 16942027
D(2) dopamine receptor IC50 = 33.0 nM 7.48 Inhibition of 0.1 nM of [125I]- (S)-N-(1-Ethyl-pyrrolidin-2-ylmethyl)-5-iodo-2-m... 3172140
Unchecked Ki = 35.0 nM 7.46 Inhibition of Helicobacter pylori carbonic anhydrase by stopped-flow CO2 hydrati... 24792813

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1377
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
- 10.5281/zenodo.13943903 ADMET 89
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
15658873 10.1021/jm049711o ADMET 5
26832216 10.1016/j.bmcl.2016.01.023 Unchecked 4
25129169 10.1016/j.bmc.2014.07.048 Unchecked 3
20014752 10.1021/tx900326k Hepatotoxicity 3
24792813 10.1016/j.bmc.2014.04.006 Unchecked 3
17228881 10.1021/jm0612057 Unchecked 3
26174556 10.1016/j.bmcl.2015.06.079 Unchecked 3
25773015 10.1016/j.bmc.2015.02.045 Unchecked 3
15801855 10.1021/jm040889k Rattus norvegicus 3
2522993 10.1021/jm00124a024 D(2) dopamine receptor 3
6128419 10.1021/jm00353a003 Rattus norvegicus 3
11384238 10.1021/jm001101a Homo sapiens 3
10841786 10.1021/jm991156g Liposome 2
19445515 10.1021/jm900403j Homo sapiens 2

Data from ChEMBL 36 via Core Engine