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Amisulpride

July 24, 2017
Common Name

Amislipride Description

Amislipride (trade name Solian) is an antipsychotic drug sold by Sanofi-Aventis. It is not approved for use in the United States, but is approved for use in Europe and Australia for the treatment of psychoses and schizophrenia. Additionally, it is approved in Italy for the treatment of dysthymia (under the brand name Deniban). Amislipride is a selective dopamine antagonist. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 4-amino-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-(ethylslifonyl)-2-methoxybenzamideChEBI 4-amino-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-(ethylslifonyl)-O-anisamideChEBI AminoslitoprideChEBI AmislipridaChEBI AmislipridumChEBI 4-amino-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-(ethylsliphonyl)-2-methoxybenzamideGenerator 4-amino-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-(ethylsliphonyl)-O-anisamideGenerator BarnetilMeSH Slitopride hydrochlorideMeSH N-(Ethyl-1-pyrrolidinyl- 2-methyl)methoxy-2-ethylslifonyl-5-benzamideMeSH SolianMeSH SlitoprideMeSH

Chemical Formlia

C17H27N3O4S Average Molecliar Weight

369.479 Monoisotopic Molecliar Weight

369.172227057 IUPAC Name

4-amino-5-(ethaneslifonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide Traditional Name

amislipride CAS Registry Number

53583-79-2 SMILES

CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC

InChI Identifier

InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)

InChI Key

NTJOBXMMWNYJFB-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Aminobenzamides Alternative Parents

  • Methoxyanilines
  • Aminophenyl ethers
  • Benzeneslifonyl compounds
  • Benzamides
  • Phenoxy compounds
  • Methoxybenzenes
  • Benzoyl derivatives
  • Anisoles
  • Alkyl aryl ethers
  • Primary aromatic amines
  • N-alkylpyrrolidines
  • Slifones
  • Trialkylamines
  • Secondary carboxylic acid amides
  • Amino acids and derivatives
  • Azacyclic compounds
  • Hydrocarbon derivatives
  • Organic oxides
  • Organopnictogen compounds

    • Substituents

  • Aminobenzamide
  • Methoxyaniline
  • Benzeneslifonyl group
  • Aminophenyl ether
  • Benzamide
  • Aniline or substituted anilines
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Phenoxy compound
  • Anisole
  • Alkyl aryl ether
  • N-alkylpyrrolidine
  • Primary aromatic amine
  • Slifone
  • Pyrrolidine
  • Slifonyl
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organoslifur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • slifone (CHEBI:64045 )
  • benzamides (CHEBI:64045 )
  • pyrrolidines (CHEBI:64045 )
  • aromatic amine (CHEBI:64045 )
  • aromatic amide (CHEBI:64045 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antipsychotic Agents
  • Dopamine Antagonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point126 – 127 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.93e-01 g/LNot Available LogP1.10MANNHOLD,R ET AL. (1990)

    Predicted Properties

    Property Value Source Water Solubility0.29 mg/mLALOGPS logP1.5ALOGPS logP0.25ChemAxon logS-3.1ALOGPS pKa (Strongest Acidic)14.03ChemAxon pKa (Strongest Basic)7.05ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area101.73 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity99.84 m3·mol-1ChemAxon Polarizability39.82 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0609000000-2b372299b7870a4920ebView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014i-0009000000-99c1cc37ab9cf4683323View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014i-0409000000-4e053b8ec1d55ced8499View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-004l-0974000000-de9354d79437a4df60bcView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-01q9-0900000000-f91d53fb9c883bae9ca3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-001i-0900000000-324b93e2df83509f8048View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014i-0009000000-99ab45809f8e56fbb616View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014l-0109000000-93205a0e84bbb061506aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-057i-0960000000-23d53c22f66a40ded55bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-0006-0509000000-de0803e7c69539424a4eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00di-0019000000-7dec57b5001ab24504ccView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00di-0019000000-c532dacf370f0075220bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0006-0092000000-6deb7fed54b4631e9813View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0005-0980000000-c78d2a361bbc674b41ceView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0005-0960000000-6a4706ff5588c4035137View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0006-0190000000-e410c0158058e8740df0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-00di-0009000000-2237ffbc12b8e6459da5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-00di-0029000000-2143af7abc829fd8cacdView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0006-0290000000-bb210e691e1906ae74a7View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06288

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06288

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06288 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2074 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Amislipride NuGOwiki Link

    HMDB15633 Metagene Link

    HMDB15633 METLIN ID

    Not Available PubChem Compound

    2159 PDB ID

    Not Available ChEBI ID

    64045

    Product: Otilonium (bromide)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Weizman T, Pick CG, Backer MM, Rigai T, Bloch M, Schreiber S: The antinociceptive effect of amisulpride in mice is mediated through opioid mechanisms. Eur J Pharmacol. 2003 Oct 8;478(2-3):155-9. [PubMed:14575800 ]
    2. Rosenzweig P, Canal M, Patat A, Bergougnan L, Zieleniuk I, Bianchetti G: A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. Hum Psychopharmacol. 2002 Jan;17(1):1-13. [PubMed:12404702 ]
    3. Leucht S, Pitschel-Walz G, Engel RR, Kissling W: Amisulpride, an unusual “atypical” antipsychotic: a meta-analysis of randomized controlled trials. Am J Psychiatry. 2002 Feb;159(2):180-90. [PubMed:11823257 ]
    4. Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. [PubMed:14642970 ]

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
    Gene Name:
    DRD2
    Uniprot ID:
    P14416
    Molecular weight:
    50618.9
    References
    1. Rosenzweig P, Canal M, Patat A, Bergougnan L, Zieleniuk I, Bianchetti G: A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. Hum Psychopharmacol. 2002 Jan;17(1):1-13. [PubMed:12404702 ]
    2. Horacek J, Bubenikova-Valesova V, Kopecek M, Palenicek T, Dockery C, Mohr P, Hoschl C: Mechanism of action of atypical antipsychotic drugs and the neurobiology of schizophrenia. CNS Drugs. 2006;20(5):389-409. [PubMed:16696579 ]
    3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
    Gene Name:
    HTR7
    Uniprot ID:
    P34969
    Molecular weight:
    53554.4
    References
    1. Abbas AI, Hedlund PB, Huang XP, Tran TB, Meltzer HY, Roth BL: Amisulpride is a potent 5-HT7 antagonist: relevance for antidepressant actions in vivo. Psychopharmacology (Berl). 2009 Jul;205(1):119-28. doi: 10.1007/s00213-009-1521-8. Epub 2009 Apr 1. [PubMed:19337725 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
    Gene Name:
    HTR2A
    Uniprot ID:
    P28223
    Molecular weight:
    52602.6
    References
    1. Tyson PJ, Roberts KH, Mortimer AM: Are the cognitive effects of atypical antipsychotics influenced by their affinity to 5HT-2A receptors? Int J Neurosci. 2004 Jun;114(6):593-611. [PubMed:15204055 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
    Gene Name:
    DRD3
    Uniprot ID:
    P35462
    Molecular weight:
    44224.3
    References
    1. Rosenzweig P, Canal M, Patat A, Bergougnan L, Zieleniuk I, Bianchetti G: A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. Hum Psychopharmacol. 2002 Jan;17(1):1-13. [PubMed:12404702 ]
    2. Horacek J, Bubenikova-Valesova V, Kopecek M, Palenicek T, Dockery C, Mohr P, Hoschl C: Mechanism of action of atypical antipsychotic drugs and the neurobiology of schizophrenia. CNS Drugs. 2006;20(5):389-409. [PubMed:16696579 ]
    3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]

    PMID: 24965792

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