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

Stem definitionDrug idCAS RN
sulpiride derivatives 179 71675-85-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • barhemsys
  • amisulpride
  • aminosultopride
  • deniban
  • solian
A benzamide derivative that is used as an antipsychotic agent for the treatment of schizophrenia. It is also used as an antidepressive agent.
  • Molecular weight: 369.48
  • Formula: C17H27N3O4S
  • CLOGP: 1.80
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 101.73
  • ALOGS: -3.10
  • ROTB: 7

  • Status: ONP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 46.40 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 48 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Feb. 26, 2020 FDA ACACIA PHARMA LTD
Jan. 1, 1986 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
Extrapyramidal disorder 214.73 24.69 76 6984 11192 46667810
Schizophrenia 160.21 24.69 57 7003 8511 46670491
Sopor 132.09 24.69 63 6997 19765 46659237
Hyperprolactinaemia 122.82 24.69 36 7024 2896 46676106
Blood prolactin increased 113.00 24.69 34 7026 2993 46676009
Drug abuse 108.28 24.69 84 6976 63324 46615678
Metabolic syndrome 91.84 24.69 24 7036 1260 46677742
Neuroleptic malignant syndrome 88.54 24.69 40 7020 11082 46667920
Electrocardiogram QT prolonged 85.43 24.69 67 6993 51258 46627744
Galactorrhoea 77.59 24.69 27 7033 3770 46675232
Psychotic disorder 77.09 24.69 46 7014 22575 46656427
Antipsychotic drug level increased 74.21 24.69 25 7035 3167 46675835
Hallucination, auditory 74.12 24.69 35 7025 10721 46668281
Sedation 73.97 24.69 45 7015 22865 46656137
Akathisia 71.91 24.69 31 7029 7683 46671319
Differential white blood cell count abnormal 65.23 24.69 16 7044 649 46678353
Confusional state 65.13 24.69 99 6961 159793 46519209
Mental impairment 57.77 24.69 31 7029 12425 46666577
Drug interaction 55.18 24.69 105 6955 202989 46476013
Myocarditis 49.71 24.69 24 7036 7715 46671287
Neutrophil count increased 48.59 24.69 29 7031 14224 46664778
Aggression 47.40 24.69 34 7026 22710 46656292
Tardive dyskinesia 47.26 24.69 23 7037 7520 46671482
Delusion 46.77 24.69 26 7034 11162 46667840
Dystonia 46.62 24.69 26 7034 11231 46667771
Parkinsonism 46.12 24.69 23 7037 7925 46671077
CSF measles antibody positive 45.63 24.69 8 7052 57 46678945
Mydriasis 45.42 24.69 25 7035 10528 46668474
Rubella antibody positive 44.81 24.69 8 7052 64 46678938
Overdose 44.11 24.69 65 6995 101914 46577088
Intentional self-injury 43.33 24.69 33 7027 24133 46654869
Blood brain barrier defect 42.19 24.69 8 7052 92 46678910
Type 2 diabetes mellitus 42.08 24.69 30 7030 19845 46659157
Tremor 42.02 24.69 68 6992 115571 46563431
White blood cell count increased 41.95 24.69 42 7018 44177 46634825
Salivary hypersecretion 41.43 24.69 20 7040 6425 46672577
Hallucination 41.18 24.69 44 7016 49907 46629095
Pain 40.71 24.69 11 7049 476937 46202065
Suicide attempt 39.36 24.69 45 7015 54991 46624011
Thunderclap headache 38.54 24.69 8 7052 150 46678852
Organic brain syndrome 38 24.69 8 7052 161 46678841
Accommodation disorder 37.16 24.69 9 7051 346 46678656
Mental disorder 36.68 24.69 29 7031 22396 46656606
Neutropenia 35.14 24.69 71 6989 143133 46535869
Catatonia 34.67 24.69 15 7045 3747 46675255
Negative thoughts 33.97 24.69 10 7050 815 46678187
CSF protein increased 33.94 24.69 9 7051 500 46678502
Blood folate decreased 33.13 24.69 9 7051 548 46678454
Leukopenia 33.11 24.69 46 7014 68297 46610705
Euphoric mood 32.84 24.69 15 7045 4257 46674745
Amenorrhoea 32.68 24.69 19 7041 8876 46670126
Antipsychotic drug level above therapeutic 32.67 24.69 10 7050 931 46678071
Coma 32.43 24.69 42 7018 58307 46620695
Ventricular dyskinesia 32.28 24.69 7 7053 163 46678839
Cerebral artery stenosis 31.57 24.69 8 7052 371 46678631
Grandiosity 31.36 24.69 7 7053 187 46678815
Agitation 30.97 24.69 40 7020 55375 46623627
Serotonin syndrome 30.64 24.69 27 7033 24193 46654809
Weight increased 30.64 24.69 73 6987 164400 46514602
Treatment noncompliance 29.60 24.69 29 7031 29702 46649300
Pleocytosis 29.09 24.69 8 7052 510 46678492
Hemianopia 28.74 24.69 9 7051 904 46678098
Hypochromic anaemia 28.53 24.69 10 7050 1425 46677577
Morose 28.47 24.69 5 7055 36 46678966
Cognitive disorder 27.80 24.69 31 7029 36852 46642150
Psychiatric decompensation 26.91 24.69 9 7051 1114 46677888
Cor pulmonale acute 26.68 24.69 7 7053 373 46678629
Vertigo 26.66 24.69 36 7024 52012 46626990
Cardiogenic shock 26.38 24.69 21 7039 16363 46662639
Pain in extremity 26.09 24.69 4 7056 258676 46420326
Muscle rigidity 25.72 24.69 17 7043 9944 46669058
Arthralgia 24.97 24.69 12 7048 364591 46314411
Hallucination, olfactory 24.79 24.69 6 7054 230 46678772

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
Schizophrenia 350.46 23.36 125 9372 8923 29934058
Antipsychotic drug level below therapeutic 197.32 23.36 52 9445 1320 29941661
Neuroleptic malignant syndrome 190.13 23.36 96 9401 16199 29926782
Neutrophil count increased 169.23 23.36 87 9410 15236 29927745
Akathisia 167.66 23.36 65 9432 5839 29937142
Psychotic disorder 157.18 23.36 93 9404 21422 29921559
Electrocardiogram QT prolonged 151.60 23.36 110 9387 35725 29907256
Extrapyramidal disorder 142.53 23.36 69 9428 10624 29932357
Salivary hypersecretion 135.73 23.36 60 9437 7506 29935475
Antipsychotic drug level increased 127.23 23.36 45 9452 3121 29939860
Obsessive-compulsive disorder 126.18 23.36 48 9449 4093 29938888
Disinhibition 123.19 23.36 39 9458 1918 29941063
White blood cell count increased 122.38 23.36 101 9396 39572 29903409
Blood prolactin increased 122.20 23.36 36 9461 1386 29941595
Mental impairment 121.03 23.36 59 9438 9218 29933763
Therapeutic product effect variable 114.28 23.36 34 9463 1355 29941626
Blood creatine phosphokinase increased 107.66 23.36 98 9399 43750 29899231
Euphoric mood 100.09 23.36 41 9456 4249 29938732
Antipsychotic drug level decreased 97.14 23.36 27 9470 841 29942140
Antipsychotic drug level above therapeutic 91.55 23.36 27 9470 1043 29941938
Delusion 90.58 23.36 53 9444 11936 29931045
Increased appetite 89.46 23.36 41 9456 5576 29937405
Hallucination, auditory 81.22 23.36 46 9451 9743 29933238
Suicide attempt 74.74 23.36 74 9423 36623 29906358
Aggression 72.54 23.36 73 9424 36834 29906147
Tachycardia 70.49 23.36 101 9396 73638 29869343
Obesity 70.43 23.36 40 9457 8515 29934466
Leukopenia 61.25 23.36 82 9415 56077 29886904
Sedation 59.64 23.36 46 9451 16327 29926654
Weight increased 59.32 23.36 94 9403 74819 29868162
Dystonia 58.08 23.36 37 9460 9690 29933291
Neutropenia 50.68 23.36 120 9377 128420 29814561
Agitation 48.62 23.36 72 9425 54001 29888980
Neutrophil count decreased 47.82 23.36 63 9434 42391 29900590
Dyslipidaemia 47.73 23.36 27 9470 5700 29937281
Lower respiratory tract infection 47.34 23.36 50 9447 26664 29916317
White blood cell count decreased 45.25 23.36 89 9408 83858 29859123
Hyperprolactinaemia 44.22 23.36 16 9481 1184 29941797
Breast engorgement 43.62 23.36 7 9490 9 29942972
Nausea 43.46 23.36 20 9477 296937 29646044
Parkinsonism 39.34 23.36 26 9471 7243 29935738
Drug interaction 38.87 23.36 145 9352 199423 29743558
Persecutory delusion 38.45 23.36 17 9480 2123 29940858
Sopor 38.11 23.36 30 9467 10961 29932020
Diarrhoea 37.14 23.36 31 9466 334072 29608909
Blepharospasm 36.58 23.36 13 9484 913 29942068
Therapeutic product effect incomplete 36.24 23.36 49 9448 33785 29909196
Hypoventilation 35.76 23.36 18 9479 3005 29939976
Paranoia 35.73 23.36 28 9469 10160 29932821
Pleurothotonus 35.31 23.36 13 9484 1010 29941971
Suicidal ideation 33.76 23.36 49 9448 36065 29906916
Thinking abnormal 33.70 23.36 21 9476 5290 29937691
Conduction disorder 33.46 23.36 15 9482 1936 29941045
Left ventricular dysfunction 30.73 23.36 24 9473 8667 29934314
Drug level increased 30.12 23.36 33 9464 18321 29924660
Somnolence 29.43 23.36 82 9415 96681 29846300
Prescribed overdose 28.89 23.36 23 9474 8538 29934443
Subacute endocarditis 28.64 23.36 6 9491 53 29942928
Platelet count increased 28.46 23.36 23 9474 8719 29934262
Arthralgia 27.37 23.36 5 9492 135786 29807195
Abnormal behaviour 27.26 23.36 37 9460 25586 29917395
Intentional self-injury 26.98 23.36 27 9470 13505 29929476
Eosinophil count decreased 26.78 23.36 11 9486 1146 29941835
Treatment noncompliance 26.16 23.36 36 9461 25217 29917764
Myocarditis 25.75 23.36 23 9474 9988 29932993
Impaired self-care 25.66 23.36 10 9487 908 29942073
Sarcoma metastatic 25.55 23.36 6 9491 93 29942888
Speech disorder 25.48 23.36 35 9462 24477 29918504
Disturbance in attention 25.14 23.36 33 9464 22096 29920885
Wrong patient received product 25.02 23.36 12 9485 1805 29941176
Pain 24.62 23.36 12 9485 172629 29770352
C-reactive protein increased 24.49 23.36 47 9450 43426 29899555
Hangover 24.11 23.36 10 9487 1068 29941913
Oromandibular dystonia 24.10 23.36 8 9489 457 29942524
Metabolic syndrome 23.88 23.36 11 9486 1511 29941470
Diffuse large B-cell lymphoma stage II 23.59 23.36 5 9492 47 29942934

Pharmacologic Action:

SourceCodeDescription
ATC N05AL05 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Benzamides
FDA MoA N0000175799 Dopamine D2 Antagonists
FDA EPC N0000175800 Dopamine-2 Receptor Antagonist
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:35703 xenobiotic
CHEBI has role CHEBI:65191 atypical antipsychotics
CHEBI has role CHEBI:78298 environmental contaminants

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postoperative nausea and vomiting indication 1488000
Chronic schizophrenia indication 83746006
Dysthymia off-label use 78667006 DOID:12139

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.78 acidic
pKa2 9.09 Basic
pKa3 0.54 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Feb. 26, 2020 RX SOLUTION INTRAVENOUS Feb. 26, 2025 NEW CHEMICAL ENTITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.55 WOMBAT-PK SCIENTIFIC LITERATURE
D(3) dopamine receptor GPCR ANTAGONIST Ki 8.49 WOMBAT-PK SCIENTIFIC LITERATURE
5-hydroxytryptamine receptor 7 GPCR Ki 7.94 PDSP
Alpha-2A adrenergic receptor GPCR Ki 5.95 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 5.87 PDSP
Alpha-2C adrenergic receptor GPCR Ki 5.81 PDSP
5-hydroxytryptamine receptor 1B GPCR Ki 5.76 PDSP
D(4) dopamine receptor GPCR Ki 5.63 PDSP
5-hydroxytryptamine receptor 6 GPCR Ki 5.38 PDSP
5-hydroxytryptamine receptor 2A GPCR Ki 5.08 PDSP
5-hydroxytryptamine receptor 2B GPCR Ki 7.89 PDSP
D(3) dopamine receptor GPCR ANTAGONIST Ki 7.40 IUPHAR

External reference:

IDSource
8110R61I4U UNII
D07310 KEGG_DRUG
C0103045 UMLSCUI
CHEBI:64045 CHEBI
CHEMBL243712 ChEMBL_ID
DB06288 DRUGBANK_ID
D000077582 MESH_DESCRIPTOR_UI
2159 PUBCHEM_CID
4960 INN_ID
963 IUPHAR_LIGAND_ID
2284233 RXNORM
17788 MMSL
331491 MMSL
d04990 MMSL
005229 NDDF
321636003 SNOMEDCT_US
391761004 SNOMEDCT_US
4039609 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Barhemsys HUMAN PRESCRIPTION DRUG LABEL 1 71390-125 INJECTION, SOLUTION 2.50 mg INTRAVENOUS NDA 30 sections