sulpiride Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
sulpiride derivatives 2537 15676-16-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulpiride
  • sulpirid
  • sulpitil
  • sulpyrid
  • sursumid
A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed)
  • Molecular weight: 341.43
  • Formula: C15H23N3O4S
  • CLOGP: 1.11
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 101.73
  • ALOGS: -2.80
  • ROTB: 6

Drug dosage:

DoseUnitRoute
0.80 g O
0.80 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 2.28 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 70 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 133.89 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 27 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.94 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1972 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Torsade de pointes 97.06 21.28 38 4281 12116 46669627
Parkinsonism 89.59 21.28 32 4287 7916 46673827
Electrocardiogram QT prolonged 70.35 21.28 49 4270 51276 46630467
Ventricular fibrillation 64.73 21.28 28 4291 11468 46670275
Fall 58.62 21.28 107 4212 328990 46352753
Cerebellar syndrome 50.86 21.28 17 4302 3448 46678295
Hypomagnesaemia 49.91 21.28 29 4290 22181 46659562
Extrapyramidal disorder 49.26 21.28 23 4296 11245 46670498
Persecutory delusion 43.40 21.28 14 4305 2541 46679202
Serotonin syndrome 42.52 21.28 27 4292 24193 46657550
Psychomotor retardation 36.35 21.28 13 4306 3220 46678523
Drug interaction 35.97 21.28 66 4253 203028 46478715
Rhabdomyolysis 35.34 21.28 30 4289 41879 46639864
Tension 33.92 21.28 12 4307 2880 46678863
Hypokalaemia 33.54 21.28 41 4278 87983 46593760
Metabolic syndrome 30.08 21.28 9 4310 1275 46680468
Depression 29.74 21.28 55 4264 170049 46511694
Hyponatraemia 28.99 21.28 41 4278 101291 46580452
Altered state of consciousness 28.96 21.28 21 4298 23327 46658416
Suicide attempt 28.37 21.28 30 4289 55006 46626737
Infectious mononucleosis 28.15 21.28 9 4310 1587 46680156
Somnolence 27.85 21.28 51 4268 156470 46525273
Urticaria vesiculosa 27.61 21.28 4 4315 12 46681731
Acinetobacter test positive 27.11 21.28 5 4314 83 46681660
Neuroleptic malignant syndrome 26.25 21.28 15 4304 11107 46670636
Dystonia 26.08 21.28 15 4304 11242 46670501
Nikolsky's sign 25.78 21.28 5 4314 110 46681633
Mixed anxiety and depressive disorder 25.01 21.28 5 4314 129 46681614
Social anxiety disorder 24.74 21.28 6 4313 383 46681360
Treatment noncompliance 24.48 21.28 21 4298 29710 46652033
Depressed mood 24.36 21.28 22 4297 33297 46648446
Long QT syndrome 22.37 21.28 9 4310 3071 46678672
Hyperthermia 22.17 21.28 12 4307 8002 46673741
Loss of consciousness 21.46 21.28 37 4282 108201 46573542
Cardio-respiratory arrest 21.36 21.28 27 4292 59842 46621901

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Neuroleptic malignant syndrome 94.79 21.04 42 3073 16253 29933110
Parkinsonism 46.33 21.04 20 3095 7249 29942114
Schizophrenia 45.22 21.04 21 3094 9027 29940336
Psychotic disorder 37.66 21.04 25 3090 21490 29927873
Extrapyramidal disorder 36.09 21.04 19 3096 10674 29938689
Suicide attempt 31.71 21.04 28 3087 36669 29912694
Eosinophil count decreased 29.97 21.04 9 3106 1148 29948215
Abnormal behaviour 27.17 21.04 22 3093 25601 29923762
Norovirus test positive 26.82 21.04 5 3110 78 29949285
Mean cell haemoglobin concentration decreased 26.70 21.04 8 3107 1012 29948351
Cognitive disorder 24.39 21.04 20 3095 23670 29925693
Neutrophil count decreased 22.83 21.04 25 3090 42429 29906934
Abulia 22.67 21.04 6 3109 484 29948879
Red cell distribution width increased 22.01 21.04 10 3105 4084 29945279
Stupor 21.72 21.04 9 3106 2944 29946419

Pharmacologic Action:

SourceCodeDescription
ATC N05AL01 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Benzamides
MeSH PA D000928 Antidepressive Agents
MeSH PA D018687 Antidepressive Agents, Second-Generation
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:35469 thymoanaleptics
CHEBI has role CHEBI:35476 grosser tranquilizer
CHEBI has role CHEBI:48561 dopamine blocker
CHEBI has role CHEBI:50919 antiemetico

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Schizophrenia indication 58214004 DOID:5419

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.47 acidic
pKa2 12.66 acidic
pKa3 8.85 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.12 CHEMBL IUPHAR
Carbonic anhydrase 2 Enzyme IC50 7.40 WOMBAT-PK
Carbonic anhydrase 12 Enzyme Ki 8.41 CHEMBL
D(4) dopamine receptor GPCR Ki 5.68 CHEMBL
D(3) dopamine receptor GPCR Ki 8.10 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 4.97 CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.76 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 8.44 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 7.51 CHEMBL
Carbonic anhydrase 1 Enzyme Ki 5.92 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 7.74 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 9.10 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.12 DRUG MATRIX
Dopamine receptor GPCR Ki 5.80 CHEMBL
Alpha carbonic anhydrase Unclassified Ki 6.37 CHEMBL
Astrosclerin-3 Unclassified Ki 6.42 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 5.64 CHEMBL
Carbonic anhydrase Unclassified Ki 6.38 CHEMBL
Delta carbonic anhydrase Unclassified Ki 6.59 CHEMBL
Carbonic anhydrase Enzyme Ki 6.91 CHEMBL
D(2) dopamine receptor GPCR IC50 6.70 CHEMBL
D(2) dopamine receptor GPCR Kd 8.82 CHEMBL
Carbonic anhydrase Enzyme Ki 6.75 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 7.14 CHEMBL
Carbonic anhydrase Enzyme Ki 7.40 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.58 CHEMBL
Carbonic anhydrase Unclassified Ki 7.53 CHEMBL
Carbonic anhydrase Enzyme Ki 6.95 CHEMBL

External reference:

IDSource
N0000166882 NUI
D01226 KEGG_DRUG
C0038803 UMLSCUI
CHEBI:32168 CHEBI
CHEMBL26 ChEMBL_ID
D013469 MESH_DESCRIPTOR_UI
2359 INN_ID
DB00391 DRUGBANK_ID
7MNE9M8287 UNII
5355 PUBCHEM_CID
5501 IUPHAR_LIGAND_ID
10239 RXNORM
003764 NDDF
321506004 SNOMEDCT_US
395891007 SNOMEDCT_US

Pharmaceutical products:

None