sulpiride ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
sulpiride derivatives and analogues 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: 1.15
  • 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 ยตM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2B,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,EIF2AK3,EPHB4,ERBB2,GRK2,ITK,MAP3K7,MAPK7,MAPKAPK2,NTRK2,PDK1,PDK2,PDK4,PIK3CB,PRKDC,SIK2,SIK3,TEK 24
kinase-selectivity-class EIF2AK3,GRK2,PDK1,SIK2,TEK 5
mdck-mdr1-bcrp-efflux MDCK-MDR1-BCRP efflux ratio 1.476 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
rat-kpuu-brain Rat brain Kpuu 0.012 % High 1

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
Electrocardiogram QT prolonged 145.01 24.33 71 4419 72385 90551572
Suicide attempt 116.29 24.33 62 4428 75337 90548620
Torsade de pointes 115.90 24.33 39 4451 15143 90608814
Parkinsonism 87.45 24.33 31 4459 14034 90609923
Drug interaction 71.85 24.33 78 4412 276375 90347582
Hypokalaemia 71.41 24.33 56 4434 131060 90492897
Toxicity to various agents 67.55 24.33 77 4413 287769 90336188
Ventricular fibrillation 65.30 24.33 25 4465 14019 90609938
Cerebellar syndrome 63.97 24.33 18 4472 3854 90620103
Somnolence 59.60 24.33 62 4428 209022 90414935
Serotonin syndrome 57.91 24.33 31 4459 37856 90586101
Fall 57.89 24.33 93 4397 481717 90142240
Hypomagnesaemia 56.88 24.33 30 4460 35558 90588399
Altered state of consciousness 54.45 24.33 28 4462 31504 90592453
Rhabdomyolysis 49.19 24.33 31 4459 51225 90572732
Drug abuse 48.78 24.33 37 4453 82310 90541647
Extrapyramidal disorder 48.27 24.33 21 4469 16282 90607675
Fracture 48.20 24.33 23 4467 22053 90601904
Psychomotor retardation 47.46 24.33 15 4475 4774 90619183
Intentional overdose 46.61 24.33 38 4452 93796 90530161
Hyponatraemia 40.54 24.33 41 4449 133497 90490460
Cardio-respiratory arrest 38.78 24.33 29 4461 63111 90560846
Product monitoring error 35.95 24.33 12 4478 4532 90619425
Tension 34.29 24.33 11 4479 3671 90620286
Long QT syndrome 33.29 24.33 11 4479 4026 90619931
Metabolic syndrome 32.23 24.33 9 4481 1873 90622084
Infectious mononucleosis 31.60 24.33 9 4481 2012 90621945
Persecutory delusion 31.59 24.33 10 4480 3198 90620759
Enuresis 30.98 24.33 10 4480 3404 90620553
Loss of consciousness 30.27 24.33 36 4454 140202 90483755
Syncope 30.20 24.33 35 4455 132628 90491329
Hyperthermia 29.58 24.33 13 4477 10322 90613635
Dystonia 29.21 24.33 15 4475 16804 90607153
Hepatic function abnormal 25.64 24.33 20 4470 46268 90577689
Social anxiety disorder 25.56 24.33 6 4484 627 90623330
Blood lactic acid increased 24.98 24.33 11 4479 8767 90615190
Salivary hypersecretion 24.61 24.33 11 4479 9081 90614876

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
Suicide attempt 77.38 24.68 43 2558 46057 42572677
Ketoacidosis 58.60 24.68 19 2582 5333 42613401
Extrapyramidal disorder 56.55 24.68 25 2576 16387 42602347
Neuroleptic malignant syndrome 53.11 24.68 26 2575 21446 42597288
Schizophrenia 52.91 24.68 21 2580 10529 42608205
Reduced facial expression 51.27 24.68 13 2588 1520 42617214
Dissociative disorder 50.57 24.68 11 2590 661 42618073
Mental impairment 46.45 24.68 20 2581 12297 42606437
Mean cell haemoglobin concentration decreased 36.72 24.68 10 2591 1540 42617194
Parkinsonism 35.99 24.68 16 2585 10607 42608127
Disturbance in attention 34.70 24.68 22 2579 29844 42588890
Panic attack 32.25 24.68 15 2586 11030 42607704
Dissociation 31.71 24.68 11 2590 3787 42614947
Depressed mood 29.11 24.68 18 2583 23366 42595368
Pneumonia aspiration 28.60 24.68 24 2577 50054 42568680
Eosinophil count decreased 28.49 24.68 10 2591 3566 42615168
Thinking abnormal 28.22 24.68 12 2589 7149 42611585
Bradyphrenia 28.22 24.68 11 2590 5251 42613483
Mental disorder 27.98 24.68 16 2585 18013 42600721
Cognitive disorder 27.36 24.68 20 2581 34152 42584582
Fear 26.27 24.68 13 2588 10952 42607782
Toxicity to various agents 25.41 24.68 48 2553 229088 42389646
Suicidal ideation 25.29 24.68 22 2579 48139 42570595
Product prescribing error 24.88 24.68 17 2584 26095 42592639

FDA Adverse Event Reporting System (Geriatric)

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
Suicide attempt 151.62 22.42 90 7022 103304 110478883
Electrocardiogram QT prolonged 149.82 22.42 91 7021 108869 110473318
Parkinsonism 118.82 22.42 47 7065 22140 110560047
Torsade de pointes 94.16 22.42 40 7072 22560 110559627
Extrapyramidal disorder 94.11 22.42 43 7069 28824 110553363
Neuroleptic malignant syndrome 69.87 22.42 37 7075 34022 110548165
Toxicity to various agents 68.85 22.42 116 6996 480439 110101748
Psychomotor retardation 61.74 22.42 22 7090 7770 110574417
Fall 59.36 22.42 124 6988 603358 109978829
Cerebellar syndrome 58.41 22.42 20 7092 6282 110575905
Altered state of consciousness 56.59 22.42 39 7073 57587 110524600
Somnolence 55.30 22.42 81 7031 297368 110284819
Hypokalaemia 54.80 22.42 63 7049 182385 110399802
Mental impairment 53.35 22.42 27 7085 22612 110559575
Serotonin syndrome 48.79 22.42 36 7076 59117 110523070
Dissociative disorder 48.15 22.42 12 7100 1239 110580948
Rhabdomyolysis 47.43 22.42 48 7064 120353 110461834
Ketoacidosis 45.84 22.42 19 7093 10068 110572119
Drug abuse 44.64 22.42 56 7056 177355 110404832
Cognitive disorder 44.16 22.42 40 7072 87471 110494716
Intentional overdose 43.61 22.42 48 7064 132453 110449734
Product prescribing error 41.79 22.42 31 7081 51300 110530887
Hypomagnesaemia 41.56 22.42 33 7079 60337 110521850
Drug interaction 41.42 22.42 96 7016 500087 110082100
Depressed mood 41.35 22.42 33 7079 60776 110521411
Fracture 40.02 22.42 23 7089 24765 110557422
Schizophrenia 39.98 22.42 22 7090 21804 110560383
Hepatic function abnormal 39.62 22.42 38 7074 89257 110492930
Reduced facial expression 39.43 22.42 13 7099 3638 110578549
Tension 38.95 22.42 14 7098 5064 110577123
Ventricular fibrillation 33.74 22.42 25 7087 41288 110540899
Disturbance in attention 30.61 22.42 28 7084 61967 110520220
Panic attack 29.38 22.42 20 7092 28920 110553267
Hyponatraemia 29.04 22.42 51 7061 217602 110364585
Mental disorder 28.41 22.42 22 7090 38769 110543418
Pneumonia aspiration 27.71 22.42 30 7082 81203 110500984
Overdose 27.66 22.42 52 7060 233742 110348445
Hyperthermia 27.22 22.42 17 7095 21255 110560932
Cardio-respiratory arrest 26.66 22.42 35 7077 115801 110466386
Dystonia 26.59 22.42 18 7094 25787 110556400
Fear 25.88 22.42 17 7095 23176 110559011
Suicidal ideation 25.78 22.42 31 7081 93906 110488281
Product monitoring error 25.06 22.42 12 7100 8915 110573272
Bradyphrenia 24.78 22.42 13 7099 11715 110570472
Atopic keratoconjunctivitis 24.59 22.42 4 7108 45 110582142
Long QT syndrome 24.44 22.42 11 7101 7107 110575080
Anxiety 24.00 22.42 62 7050 345016 110237171
Mean cell haemoglobin concentration decreased 23.47 22.42 10 7102 5672 110576515
Enuresis 23.05 22.42 9 7103 4087 110578100
Eosinophil count decreased 22.91 22.42 10 7102 6008 110576179
Neutrophil count decreased 22.52 22.42 33 7079 120908 110461279

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AL01 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Benzamides
MeSH PA D000928 Antidepressive Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014150 Antipsychotic Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D018687 Antidepressive Agents, Second-Generation
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:50919 antiemetic

Related Drugs by ATC class:

N05AL Benzamides 6 drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Schizophrenia indication 58214004 DOID:5419




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Alpha-2A adrenergic receptor GPCR Ki 6.12 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 8.10 CHEMBL
D(4) dopamine receptor GPCR Ki 5.68 CHEMBL
Carbonic anhydrase 2 Enzyme IC50 7.40 WOMBAT-PK
Carbonic anhydrase 1 Enzyme Ki 5.92 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 7.51 CHEMBL
Carbonic anhydrase 12 Enzyme Ki 8.41 CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.76 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 7.74 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 8.44 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 4.97 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 9.10 CHEMBL
Carbonic anhydrase Enzyme Ki 6.75 CHEMBL
D(2) dopamine receptor GPCR Kd 8.82 CHEMBL
D(2) dopamine receptor GPCR IC50 6.70 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 7.14 CHEMBL
Carbonic anhydrase Enzyme Ki 6.91 CHEMBL
Carbonic anhydrase Enzyme Ki 7.40 CHEMBL
Carbonic anhydrase Enzyme Ki 6.95 CHEMBL
Alpha carbonic anhydrase Enzyme Ki 6.37 CHEMBL
Carbonic anhydrase Enzyme Ki 6.38 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.09 CHEMBL
Astrosclerin-3 Enzyme Ki 6.42 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 5.64 CHEMBL
Delta carbonic anhydrase Enzyme Ki 6.59 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.58 CHEMBL
Dopamine receptor GPCR Ki 5.80 CHEMBL
Carbonic anhydrase Enzyme Ki 7.53 CHEMBL
Carbonic anhydrase, alpha family Enzyme Ki 6.06 CHEMBL
Carbonate dehydratase Enzyme Ki 7.17 CHEMBL

External reference:

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

Pharmaceutical products:

None