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
7.50 mg P

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 233.17 24.18 82 7680 12320 53328984
Schizophrenia 174.40 24.18 63 7699 10216 53331088
Hyperprolactinaemia 150.68 24.18 43 7719 3272 53338032
Sopor 146.05 24.18 68 7694 21016 53320288
Drug abuse 138.06 24.18 97 7665 65429 53275875
Blood prolactin increased 125.00 24.18 37 7725 3202 53338102
Electrocardiogram QT prolonged 103.91 24.18 77 7685 56326 53284978
Neuroleptic malignant syndrome 102.97 24.18 45 7717 11988 53329316
Galactorrhoea 96.91 24.18 32 7730 3963 53337341
Akathisia 96.61 24.18 39 7723 8532 53332772
Metabolic syndrome 90.13 24.18 24 7738 1410 53339894
Psychotic disorder 88.63 24.18 51 7711 24334 53316970
Antipsychotic drug level increased 82.01 24.18 27 7735 3312 53337992
Hallucination, auditory 78.48 24.18 37 7725 11736 53329568
Parkinsonism 74.82 24.18 33 7729 8980 53332324
Mental impairment 71.23 24.18 36 7726 13273 53328031
Drug interaction 68.70 24.18 118 7644 219211 53122093
Myocarditis 67.06 24.18 30 7732 8438 53332866
Sedation 64.90 24.18 45 7717 29630 53311674
Differential white blood cell count abnormal 64.15 24.18 16 7746 724 53340580
Confusional state 62.79 24.18 106 7656 194115 53147189
Aggression 54.75 24.18 37 7725 23366 53317938
Mydriasis 53.01 24.18 28 7734 11298 53330006
Pain 52.40 24.18 11 7751 588387 52752917
Dystonia 52.06 24.18 29 7733 12992 53328312
Suicide attempt 50.99 24.18 52 7710 58116 53283188
Tremor 50.75 24.18 76 7686 125660 53215644
Tardive dyskinesia 49.63 24.18 24 7738 8046 53333258
Delusion 48.71 24.18 27 7735 11982 53329322
Neutrophil count increased 47.70 24.18 29 7733 15281 53326023
Salivary hypersecretion 46.82 24.18 22 7740 6921 53334383
Overdose 46.17 24.18 67 7695 107669 53233635
CSF measles antibody positive 45.94 24.18 8 7754 57 53341247
Rubella antibody positive 45.12 24.18 8 7754 64 53341240
Hallucination 43.36 24.18 46 7716 53792 53287512
Intentional self-injury 43.14 24.18 33 7729 25251 53316053
Neutropenia 42.54 24.18 80 7682 159105 53182199
Blood brain barrier defect 42.03 24.18 8 7754 98 53341206
Mental disorder 41.99 24.18 32 7730 24344 53316960
White blood cell count increased 41.73 24.18 42 7720 46203 53295101
Catatonia 40.80 24.18 17 7745 4023 53337281
Treatment noncompliance 37.38 24.18 34 7728 33001 53308303
Thunderclap headache 37.25 24.18 8 7754 185 53341119
Antipsychotic drug level decreased 36.69 24.18 8 7754 199 53341105
Accommodation disorder 36.52 24.18 9 7753 387 53340917
Organic brain syndrome 35.92 24.18 8 7754 220 53341084
Grandiosity 35.82 24.18 8 7754 223 53341081
Euphoric mood 35.71 24.18 16 7746 4513 53336791
CSF protein increased 34.07 24.18 9 7753 512 53340792
Loss of consciousness 33.77 24.18 60 7702 114152 53227152
Leukopenia 33.38 24.18 47 7715 73416 53267888
Coma 33.37 24.18 43 7719 61740 53279564
Negative thoughts 33.18 24.18 10 7752 919 53340385
Ventricular dyskinesia 32.80 24.18 7 7755 157 53341147
Type 2 diabetes mellitus 32.75 24.18 31 7731 31639 53309665
Bladder trabeculation 32.73 24.18 6 7756 59 53341245
Amenorrhoea 32.48 24.18 19 7743 9330 53331974
Blood folate decreased 32.44 24.18 9 7753 617 53340687
Antipsychotic drug level above therapeutic 32.11 24.18 10 7752 1026 53340278
Agitation 31.97 24.18 41 7721 58585 53282719
Binge eating 30.75 24.18 8 7754 429 53340875
Cerebral artery stenosis 30.46 24.18 8 7754 445 53340859
Arthralgia 30.44 24.18 13 7749 439770 52901534
Rash 29.61 24.18 14 7748 446177 52895127
Serotonin syndrome 29.52 24.18 27 7735 26379 53314925
Pruritus 29.37 24.18 4 7758 293828 53047476
Intentional overdose 29.06 24.18 42 7720 67163 53274141
Waxy flexibility 28.77 24.18 6 7756 120 53341184
Morose 28.66 24.18 5 7757 36 53341268
Hemianopia 28.60 24.18 9 7753 955 53340349
Pain in extremity 28.21 24.18 4 7758 285046 53056258
Pleocytosis 28.17 24.18 8 7754 597 53340707
Muscle rigidity 27.42 24.18 18 7744 10823 53330481
Vertigo 27.15 24.18 37 7725 56044 53285260
Weight increased 27.06 24.18 78 7684 204489 53136815
Electrocardiogram T wave abnormal 26.98 24.18 11 7751 2465 53338839
Cor pulmonale acute 26.86 24.18 7 7755 378 53340926
Hypochromic anaemia 26.22 24.18 10 7752 1879 53339425
Cardiogenic shock 25.90 24.18 21 7741 17461 53323843
Psychiatric decompensation 25.55 24.18 9 7753 1353 53339951
Toxicity to various agents 25.53 24.18 80 7682 219518 53121786
Cognitive disorder 25.49 24.18 32 7730 44746 53296558
Hallucination, olfactory 24.84 24.18 6 7756 237 53341067

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 371.85 23.69 134 10179 9850 32493363
Antipsychotic drug level below therapeutic 318.90 23.69 82 10231 1887 32501326
Akathisia 252.91 23.69 92 10221 6933 32496280
Disinhibition 225.68 23.69 67 10246 2653 32500560
Obsessive-compulsive disorder 217.05 23.69 75 10238 4859 32498354
Therapeutic product effect variable 215.51 23.69 61 10252 2035 32501178
Neuroleptic malignant syndrome 189.35 23.69 98 10215 17397 32485816
Euphoric mood 186.42 23.69 68 10245 5159 32498054
Increased appetite 172.24 23.69 68 10245 6408 32496805
Neutrophil count increased 167.89 23.69 88 10225 16026 32487187
Psychotic disorder 156.42 23.69 95 10218 22925 32480288
Electrocardiogram QT prolonged 154.84 23.69 116 10197 39525 32463688
Antipsychotic drug level increased 148.60 23.69 52 10261 3494 32499719
Extrapyramidal disorder 138.43 23.69 70 10243 11825 32491388
Salivary hypersecretion 135.03 23.69 61 10252 8027 32495186
Suicide attempt 127.71 23.69 102 10211 38142 32465071
Blood prolactin increased 126.46 23.69 38 10275 1567 32501646
White blood cell count increased 120.61 23.69 102 10211 41300 32461913
Mental impairment 116.73 23.69 59 10254 9953 32493260
Blood creatine phosphokinase increased 104.54 23.69 98 10215 45378 32457835
Obesity 104.28 23.69 55 10258 10127 32493086
Leukopenia 102.23 23.69 110 10203 60012 32443201
Weight increased 95.73 23.69 125 10188 83538 32419675
Antipsychotic drug level decreased 95.34 23.69 27 10286 901 32502312
Antipsychotic drug level above therapeutic 93.56 23.69 28 10285 1138 32502075
Delusion 88.74 23.69 54 10259 13054 32490159
Hallucination, auditory 81.46 23.69 47 10266 10303 32492910
Dyslipidaemia 78.58 23.69 40 10273 6843 32496370
Therapeutic product effect incomplete 70.85 23.69 76 10237 41265 32461948
Aggression 68.53 23.69 73 10240 39316 32463897
Tachycardia 67.86 23.69 103 10210 78985 32424228
Prescribed overdose 61.32 23.69 38 10275 9481 32493732
Hyperprolactinaemia 57.79 23.69 20 10293 1298 32501915
Dystonia 57.50 23.69 38 10275 10585 32492628
Sedation 56.68 23.69 47 10266 18479 32484734
Leukaemia 53.91 23.69 26 10287 3960 32499253
Neutropenia 52.02 23.69 129 10184 142046 32361167
Nausea 49.56 23.69 20 10293 320829 32182384
Agitation 46.88 23.69 73 10240 57163 32446050
Diarrhoea 44.23 23.69 31 10282 364771 32138442
Breast engorgement 43.61 23.69 7 10306 9 32503204
Lower respiratory tract infection 43.59 23.69 50 10263 29193 32474020
White blood cell count decreased 43.57 23.69 92 10221 91106 32412107
Neutrophil count decreased 42.68 23.69 63 10250 47076 32456137
Drug interaction 39.55 23.69 155 10158 218030 32285183
Schizoaffective disorder 39.24 23.69 15 10298 1293 32501920
Psychotic symptom 37.55 23.69 15 10298 1454 32501759
Parkinsonism 37.45 23.69 26 10287 7843 32495370
Persecutory delusion 36.99 23.69 17 10296 2322 32500891
Sopor 36.33 23.69 30 10283 11719 32491494
Pleurothotonus 34.61 23.69 13 10300 1068 32502145
Suicidal ideation 34.61 23.69 51 10262 38032 32465181
Blepharospasm 34.30 23.69 13 10300 1095 32502118
Paranoia 34.28 23.69 28 10285 10771 32492442
Hypoventilation 34.04 23.69 18 10295 3326 32499887
Conduction disorder 33.16 23.69 15 10298 1975 32501238
Thinking abnormal 32.55 23.69 21 10292 5614 32497599
Somnolence 31.59 23.69 88 10225 103709 32399504
Drug ineffective 31.29 23.69 218 10095 383259 32119954
Disturbance in attention 31.07 23.69 38 10275 23715 32479498
Arthralgia 30.96 23.69 5 10308 148443 32354770
Left ventricular dysfunction 30.49 23.69 25 10288 9670 32493543
Platelet count increased 29.51 23.69 24 10289 9177 32494036
Drug level increased 29.35 23.69 34 10279 20046 32483167
Abnormal behaviour 29.34 23.69 39 10274 26427 32476786
Subacute endocarditis 28.64 23.69 6 10307 53 32503160
Diffuse large B-cell lymphoma stage II 28.54 23.69 6 10307 54 32503159
Pain 28.39 23.69 12 10301 187544 32315669
Treatment noncompliance 27.01 23.69 38 10275 27164 32476049
Overdose 26.65 23.69 74 10239 87003 32416210
Myocarditis 26.62 23.69 25 10288 11565 32491648
Intentional self-injury 26.36 23.69 27 10286 13873 32489340
Toxicity to various agents 26.36 23.69 119 10194 177922 32325291
Eosinophil count decreased 25.68 23.69 11 10302 1272 32501941
Sarcoma metastatic 25.49 23.69 6 10307 94 32503119
Pain in extremity 24.80 23.69 4 10309 118897 32384316
Hangover 23.92 23.69 10 10303 1089 32502124
Impaired self-care 23.78 23.69 10 10303 1105 32502108

Pharmacologic Action:

SourceCodeDescription
ATC N05AL05 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
FDA MoA N0000175799 Dopamine D2 Antagonists
FDA EPC N0000175800 Dopamine-2 Receptor Antagonist
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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
10MG/4ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Sept. 1, 2020 RX SOLUTION INTRAVENOUS 9084765 March 10, 2031 PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Sept. 1, 2020 RX SOLUTION INTRAVENOUS 9084765 March 10, 2031 TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Sept. 1, 2020 RX SOLUTION INTRAVENOUS 9545426 March 10, 2031 PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Sept. 1, 2020 RX SOLUTION INTRAVENOUS 9545426 March 10, 2031 TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Sept. 1, 2020 RX SOLUTION INTRAVENOUS 9889118 March 10, 2031 PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Sept. 1, 2020 RX SOLUTION INTRAVENOUS 9889118 March 10, 2031 TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Feb. 26, 2020 RX SOLUTION INTRAVENOUS 9084765 March 10, 2031 PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Feb. 26, 2020 RX SOLUTION INTRAVENOUS 9084765 March 10, 2031 TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Feb. 26, 2020 RX SOLUTION INTRAVENOUS 9545426 March 10, 2031 PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Feb. 26, 2020 RX SOLUTION INTRAVENOUS 9545426 March 10, 2031 TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Feb. 26, 2020 RX SOLUTION INTRAVENOUS 9889118 March 10, 2031 PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Feb. 26, 2020 RX SOLUTION INTRAVENOUS 9889118 March 10, 2031 TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
10MG/4ML (2.5MG/ML) BARHEMSYS ACACIA N209510 Sept. 1, 2020 RX SOLUTION INTRAVENOUS Feb. 26, 2025 NEW CHEMICAL ENTITY
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 8.50 WOMBAT-PK SCIENTIFIC LITERATURE
5-hydroxytryptamine receptor 2B GPCR Ki 7.89 PDSP
5-hydroxytryptamine receptor 6 GPCR Ki 5.38 PDSP
5-hydroxytryptamine receptor 7 GPCR Ki 7.94 PDSP
5-hydroxytryptamine receptor 1B GPCR Ki 5.76 PDSP
Alpha-2A adrenergic receptor GPCR Ki 5.95 PDSP
Alpha-2C adrenergic receptor GPCR Ki 5.81 PDSP
D(4) dopamine receptor GPCR Ki 5.63 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 5.87 PDSP
5-hydroxytryptamine receptor 2A GPCR Ki 5.08 PDSP
D(3) dopamine receptor GPCR ANTAGONIST Ki 7.40 IUPHAR

External reference:

IDSource
D07310 KEGG_DRUG
2284233 RXNORM
C0103045 UMLSCUI
CHEBI:64045 CHEBI
CHEMBL243712 ChEMBL_ID
DB06288 DRUGBANK_ID
D000077582 MESH_DESCRIPTOR_UI
2159 PUBCHEM_CID
963 IUPHAR_LIGAND_ID
4960 INN_ID
8110R61I4U UNII
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