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Identification
NameAmisulpride
Accession NumberDB06288
TypeSmall Molecule
GroupsApproved, Investigational
Description

Amisulpride (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). Amisulpride is a selective dopamine antagonist.

Structure
Thumb
Synonyms
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-O-anisamide
Aminosultopride
Amisulprida
Amisulpridum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DenibanSanofi-Aventis
SolianSanofi-Aventis
Brand mixturesNot Available
SaltsNot Available
Categories
UNII8110R61I4U
CAS number71675-85-9
WeightAverage: 369.479
Monoisotopic: 369.172227057
Chemical FormulaC17H27N3O4S
InChI KeyNTJOBXMMWNYJFB-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
SMILES
CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzoic acids and derivatives. These are benzoic acids (or derivative thereof) containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids and derivatives
Alternative Parents
Substituents
  • Salicylamide
  • Aminobenzoic acid or derivatives
  • Methoxyaniline
  • Benzamide
  • Aminobenzamide
  • Methoxybenzene
  • Substituted aniline
  • Phenol ether
  • Benzoyl
  • Anisole
  • Aniline
  • Alkyl aryl ether
  • N-alkylpyrrolidine
  • Primary aromatic amine
  • Sulfonyl
  • Sulfone
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationInvestigated for use/treatment in schizophrenia and schizoaffective disorders, mania in bipolar disorder, and depression.
PharmacodynamicsNot Available
Mechanism of actionAmisulpride binds selectively to dopamine D(2) and D(3) receptors in the limbic system. Low doses of amisulpride preferentially block presynaptic D(2)/D(3)-dopamine autoreceptors, thereby enhancing dopaminergic transmission, whereas higher doses block postsynaptic receptors, thus inhibiting dopaminergic hyperactivity. It may also have 5-ht7 antagonistic effect, useful in depression treatment.
Related Articles
AbsorptionBioavailability is 48% following oral administration.
Volume of distributionNot Available
Protein bindingLow (17%)
MetabolismNot Available
Route of eliminationNot Available
Half lifeApproximately 12 hours
ClearanceNot Available
ToxicityOverdoses of amisulpride have been linked with torsades de pointes.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.864
Blood Brain Barrier+0.9441
Caco-2 permeable-0.7127
P-glycoprotein substrateSubstrate0.7242
P-glycoprotein inhibitor INon-inhibitor0.8209
P-glycoprotein inhibitor IINon-inhibitor0.8668
Renal organic cation transporterNon-inhibitor0.7899
CYP450 2C9 substrateNon-substrate0.794
CYP450 2D6 substrateNon-substrate0.8272
CYP450 3A4 substrateSubstrate0.5667
CYP450 1A2 substrateNon-inhibitor0.8888
CYP450 2C9 inhibitorNon-inhibitor0.8348
CYP450 2D6 inhibitorNon-inhibitor0.8572
CYP450 2C19 inhibitorNon-inhibitor0.8578
CYP450 3A4 inhibitorNon-inhibitor0.8942
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9081
Ames testNon AMES toxic0.5931
CarcinogenicityNon-carcinogens0.6637
BiodegradationNot ready biodegradable0.8868
Rat acute toxicity2.4706 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9398
hERG inhibition (predictor II)Inhibitor0.7128
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point181-182 °CPhysProp
logP1.06MANNHOLD,R ET AL. (1990)
pKa9.37Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.293 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceUS4401822
General 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. Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. [PubMed:14642970 ]
  3. 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 ]
  4. 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 ]
  5. Rehni AK, Singh TG, Chand P: Amisulpride-induced seizurogenic effect: a potential role of opioid receptor-linked transduction systems. Basic Clin Pharmacol Toxicol. 2011 May;108(5):310-7. doi: 10.1111/j.1742-7843.2010.00655.x. Epub 2010 Dec 22. [PubMed:21176108 ]
External Links
ATC CodesN05AL05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Amisulpride.
AmantadineThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Amantadine.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Amisulpride.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Amisulpride.
AmphetamineAmisulpride may decrease the stimulatory activities of Amphetamine.
ApomorphineThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Apomorphine.
AripiprazoleThe risk or severity of adverse effects can be increased when Aripiprazole is combined with Amisulpride.
AsenapineThe risk or severity of adverse effects can be increased when Asenapine is combined with Amisulpride.
BenzphetamineAmisulpride may decrease the stimulatory activities of Benzphetamine.
BrexpiprazoleThe risk or severity of adverse effects can be increased when Brexpiprazole is combined with Amisulpride.
BromocriptineThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Bromocriptine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Amisulpride.
CabergolineThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Cabergoline.
ChlorpromazineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Amisulpride.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Amisulpride.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Amisulpride.
ClozapineThe risk or severity of adverse effects can be increased when Clozapine is combined with Amisulpride.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Amisulpride.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Amisulpride.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Amisulpride.
DextroamphetamineAmisulpride may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Amisulpride.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Amisulpride.
DonepezilDonepezil may increase the central neurotoxic activities of Amisulpride.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Amisulpride.
DroperidolThe risk or severity of adverse effects can be increased when Droperidol is combined with Amisulpride.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Amisulpride.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Amisulpride.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Amisulpride.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Amisulpride.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Amisulpride.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Amisulpride.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Amisulpride.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Amisulpride.
FlupentixolThe risk or severity of adverse effects can be increased when Flupentixol is combined with Amisulpride.
FluphenazineThe risk or severity of adverse effects can be increased when Fluphenazine is combined with Amisulpride.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Amisulpride.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Amisulpride.
GalantamineGalantamine may increase the central neurotoxic activities of Amisulpride.
HaloperidolThe risk or severity of adverse effects can be increased when Haloperidol is combined with Amisulpride.
IloperidoneThe risk or severity of adverse effects can be increased when Iloperidone is combined with Amisulpride.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Amisulpride.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Amisulpride.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Amisulpride.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Amisulpride.
LisdexamfetamineAmisulpride may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Amisulpride.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Amisulpride.
LoxapineThe risk or severity of adverse effects can be increased when Loxapine is combined with Amisulpride.
LurasidoneThe risk or severity of adverse effects can be increased when Lurasidone is combined with Amisulpride.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Amisulpride.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Amisulpride.
MethamphetamineAmisulpride may decrease the stimulatory activities of Methamphetamine.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Methotrimeprazine is combined with Amisulpride.
MethylphenidateThe risk or severity of adverse effects can be increased when Amisulpride is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Amisulpride.
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Amisulpride.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Amisulpride.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Amisulpride.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Amisulpride.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Amisulpride.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Amisulpride.
OlanzapineThe risk or severity of adverse effects can be increased when Olanzapine is combined with Amisulpride.
PaliperidoneThe risk or severity of adverse effects can be increased when Paliperidone is combined with Amisulpride.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Amisulpride.
PerphenazineThe risk or severity of adverse effects can be increased when Perphenazine is combined with Amisulpride.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Amisulpride.
PhendimetrazineAmisulpride may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Amisulpride.
PhentermineAmisulpride may decrease the stimulatory activities of Phentermine.
PimozideThe risk or severity of adverse effects can be increased when Pimozide is combined with Amisulpride.
PramipexoleThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Pramipexole.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Amisulpride.
ProchlorperazineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with Amisulpride.
PromazineThe risk or severity of adverse effects can be increased when Promazine is combined with Amisulpride.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Amisulpride.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Amisulpride.
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Amisulpride.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Amisulpride.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Amisulpride.
RisperidoneThe risk or severity of adverse effects can be increased when Risperidone is combined with Amisulpride.
RivastigmineRivastigmine may increase the central neurotoxic activities of Amisulpride.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Amisulpride.
RopiniroleThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Ropinirole.
RotigotineThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Rotigotine.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Amisulpride.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Amisulpride.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Amisulpride.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Amisulpride.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Amisulpride.
ThioridazineThe risk or severity of adverse effects can be increased when Thioridazine is combined with Amisulpride.
ThiothixeneThe risk or severity of adverse effects can be increased when Thiothixene is combined with Amisulpride.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Amisulpride.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Amisulpride.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Amisulpride.
TrifluoperazineThe risk or severity of adverse effects can be increased when Trifluoperazine is combined with Amisulpride.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Amisulpride.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Amisulpride.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Amisulpride.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Amisulpride.
ZiprasidoneThe risk or severity of adverse effects can be increased when Ziprasidone is combined with Amisulpride.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Amisulpride.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Zuclopenthixol is combined with Amisulpride.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name:
DRD3
Uniprot ID:
P35462
Molecular Weight:
44224.335 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Serotonin receptor activity
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:
53554.43 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
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 ]
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Drug created on March 19, 2008 10:22 / Updated on March 31, 2016 09:11