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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015633
Secondary Accession Numbers
  • HMDB15633
Metabolite Identification
Common NameAmisulpride
DescriptionAmisulpride, also known as deniban or solian, belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring. Amisulpride is a very strong basic compound (based on its pKa). Another recent study concluded that amisulpride is an appropriate first-line treatment for the management of acute psychosis. The British National Formulary recommends a gradual withdrawal when discontinuing antipsychotics to avoid acute withdrawal syndrome or rapid relapse. The clinical implications of this, if any, are unclear.
Structure
Data?1582753318
Synonyms
ValueSource
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamideChEBI
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-O-anisamideChEBI
AminosultoprideChEBI
AmisulpridaChEBI
AmisulpridumChEBI
DenibanKegg
SolianKegg
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulphonyl)-2-methoxybenzamideGenerator
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulphonyl)-O-anisamideGenerator
BarnetilHMDB
Sultopride hydrochlorideHMDB
N-(Ethyl-1-pyrrolidinyl- 2-methyl)methoxy-2-ethylsulfonyl-5-benzamideHMDB
SultoprideHMDB
Chemical FormulaC17H27N3O4S
Average Molecular Weight369.479
Monoisotopic Molecular Weight369.172227057
IUPAC Name4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
Traditional Nameamisulpride
CAS Registry Number53583-79-2
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 KeyNTJOBXMMWNYJFB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzamides
Alternative Parents
Substituents
  • Aminobenzamide
  • Methoxyaniline
  • Benzamide
  • Aminophenyl ether
  • Benzenesulfonyl group
  • Phenol ether
  • Aniline or substituted anilines
  • Methoxybenzene
  • Benzoyl
  • Phenoxy compound
  • Anisole
  • Alkyl aryl ether
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Sulfone
  • Sulfonyl
  • Carboxamide group
  • Tertiary aliphatic amine
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point126 - 127 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.29 g/LNot Available
LogP1.10MANNHOLD,R ET AL. (1990)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM193.130932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.84 m³·mol⁻¹ChemAxon
Polarizability39.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.11631661259
DarkChem[M-H]-185.81831661259
DeepCCS[M+H]+184.4230932474
DeepCCS[M-H]-181.99530932474
DeepCCS[M-2H]-215.91230932474
DeepCCS[M+Na]+191.94930932474
AllCCS[M+H]+187.032859911
AllCCS[M+H-H2O]+184.332859911
AllCCS[M+NH4]+189.432859911
AllCCS[M+Na]+190.132859911
AllCCS[M-H]-183.032859911
AllCCS[M+Na-2H]-183.632859911
AllCCS[M+HCOO]-184.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AmisulprideCCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC4160.4Standard polar33892256
AmisulprideCCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC3182.2Standard non polar33892256
AmisulprideCCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC3352.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Amisulpride,1TMS,isomer #1CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC3250.4Semi standard non polar33892256
Amisulpride,1TMS,isomer #1CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC3126.0Standard non polar33892256
Amisulpride,1TMS,isomer #1CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC4391.1Standard polar33892256
Amisulpride,1TMS,isomer #2CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C3143.1Semi standard non polar33892256
Amisulpride,1TMS,isomer #2CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C3066.0Standard non polar33892256
Amisulpride,1TMS,isomer #2CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C4598.9Standard polar33892256
Amisulpride,2TMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C3198.6Semi standard non polar33892256
Amisulpride,2TMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C3235.4Standard non polar33892256
Amisulpride,2TMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C4066.4Standard polar33892256
Amisulpride,2TMS,isomer #2CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC3165.9Semi standard non polar33892256
Amisulpride,2TMS,isomer #2CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC3318.9Standard non polar33892256
Amisulpride,2TMS,isomer #2CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC4008.3Standard polar33892256
Amisulpride,3TMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C3141.7Semi standard non polar33892256
Amisulpride,3TMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C3436.2Standard non polar33892256
Amisulpride,3TMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C3683.6Standard polar33892256
Amisulpride,1TBDMS,isomer #1CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC3461.9Semi standard non polar33892256
Amisulpride,1TBDMS,isomer #1CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC3383.0Standard non polar33892256
Amisulpride,1TBDMS,isomer #1CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC4403.7Standard polar33892256
Amisulpride,1TBDMS,isomer #2CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C3385.6Semi standard non polar33892256
Amisulpride,1TBDMS,isomer #2CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C3300.3Standard non polar33892256
Amisulpride,1TBDMS,isomer #2CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C4619.2Standard polar33892256
Amisulpride,2TBDMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C3623.1Semi standard non polar33892256
Amisulpride,2TBDMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C3725.6Standard non polar33892256
Amisulpride,2TBDMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C4125.8Standard polar33892256
Amisulpride,2TBDMS,isomer #2CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC3611.3Semi standard non polar33892256
Amisulpride,2TBDMS,isomer #2CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC3794.3Standard non polar33892256
Amisulpride,2TBDMS,isomer #2CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC4032.1Standard polar33892256
Amisulpride,3TBDMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C3772.5Semi standard non polar33892256
Amisulpride,3TBDMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C4133.4Standard non polar33892256
Amisulpride,3TBDMS,isomer #1CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C3840.4Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06288 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06288 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06288
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2074
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmisulpride
METLIN IDNot Available
PubChem Compound2159
PDB IDNot Available
ChEBI ID64045
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 ]