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
Electrocardiogram QT prolonged 169.38 59.47 41 513 7773 2349758
Extrapyramidal disorder 162.37 59.47 32 522 2315 2355216
Blood prolactin increased 133.59 59.47 24 530 1043 2356488
Neuroleptic malignant syndrome 117.60 59.47 24 530 2056 2355475
Drug abuse 97.13 59.47 29 525 11997 2345534
Hyperprolactinaemia 88.71 59.47 16 538 706 2356825
Overdose 86.64 59.47 30 524 19877 2337654
Toxicity to various agents 85.94 59.47 34 520 32720 2324811
Schizophrenia 84.56 59.47 17 537 1342 2356189
Sedation 79.51 59.47 19 535 3343 2354188
Tardive dyskinesia 75.00 59.47 16 538 1688 2355843
Suicide attempt 73.10 59.47 23 531 11259 2346272
Drug ineffective 72.26 59.47 43 511 101581 2255950
Differential white blood cell count abnormal 71.78 59.47 11 543 174 2357357
Treatment noncompliance 65.44 59.47 18 536 5516 2352015
Cardiometabolic syndrome 61.53 59.47 10 544 234 2357297
Weight increased 61.26 59.47 24 530 22313 2335218

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 280.31 56.76 59 589 3089 1743044
Schizophrenia 250.42 56.76 50 598 1996 1744137
Drug ineffective 137.91 56.76 70 578 63731 1682402
Psychotic disorder 135.71 56.76 36 612 5020 1741113
Akathisia 135.62 56.76 28 620 1300 1744833
Antipsychotic drug level below therapeutic 128.96 56.76 20 628 169 1745964
Blood creatine phosphokinase increased 120.00 56.76 37 611 8819 1737314
Electrocardiogram QT prolonged 118.46 56.76 33 615 5512 1740621
Blood prolactin increased 117.16 56.76 21 627 453 1745680
Aggression 110.29 56.76 34 614 8081 1738052
Disinhibition 103.37 56.76 18 630 326 1745807
Extrapyramidal disorder 93.47 56.76 23 625 2354 1743779
Increased appetite 90.48 56.76 19 629 952 1745181
Neutropenia 86.78 56.76 35 613 18225 1727908
Tachycardia 84.22 56.76 31 617 12597 1733536
Therapeutic product effect variable 82.82 56.76 13 635 119 1746014
Overdose 79.25 56.76 32 616 16669 1729464
Sedation 75.86 56.76 21 627 3396 1742737
Hallucination, auditory 75.74 56.76 19 629 2098 1744035
Euphoric mood 75.63 56.76 16 632 829 1745304
Drug interaction 72.44 56.76 35 613 27923 1718210
Weight increased 72.43 56.76 27 621 11330 1734803
Suicide attempt 71.68 56.76 24 624 7357 1738776
Obsessive-compulsive disorder 70.23 56.76 15 633 813 1745320
Toxicity to various agents 65.11 56.76 33 615 29108 1717025
Fall 64.26 56.76 32 616 27182 1718951
Drug abuse 64.06 56.76 26 622 13663 1732470
Therapeutic product effect incomplete 62.06 56.76 20 628 5428 1740705
Salivary hypersecretion 61.71 56.76 15 633 1450 1744683
Delusion 60.18 56.76 16 632 2215 1743918
White blood cell count increased 60.12 56.76 21 627 7291 1738842
Antipsychotic drug level decreased 59.46 56.76 10 638 145 1745988
Intentional self-injury 57.32 56.76 16 632 2657 1743476

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
CHEBI has role CHEBI:65191 second generation antipsychotic
MeSH PA D014149 Tranquilizing Agents

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
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA PHARMA LTD 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 PHARMA LTD 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 PHARMA LTD 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 PHARMA LTD 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 PHARMA LTD 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 PHARMA LTD 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
5MG/2ML (2.5MG/ML) BARHEMSYS ACACIA PHARMA LTD 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 2B GPCR Ki 7.89 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 7 GPCR Ki 7.94 PDSP
D(3) dopamine receptor GPCR ANTAGONIST Ki 7.40 IUPHAR

External reference:

IDSource
D000077582 MESH_DESCRIPTOR_UI
C0103045 UMLSCUI
D07310 KEGG_DRUG
321636003 SNOMEDCT_US
391761004 SNOMEDCT_US
005229 NDDF
46303 RXNORM
8110R61I4U UNII
4960 INN_ID
CHEMBL243712 ChEMBL_ID
DB06288 DRUGBANK_ID
CHEBI:64045 CHEBI
963 IUPHAR_LIGAND_ID
2159 PUBCHEM_CID

Pharmaceutical products:

None