Amisulpride

Identification

Summary

Amisulpride is a dopamine D2 receptor antagonist used in the treatment of acute and chronic schizophrenia, and in the prevention and treatment of postoperative nausea and vomiting in adults.

Brand Names
Barhemsys
Generic Name
Amisulpride
DrugBank Accession Number
DB06288
Background

Amisulpride is a benzamide derivative and a dopamine receptor antagonist that selectively works on dopamine D2 and D3 receptors. As an antipsychotic agent, amisulpride alleviates both positive and negative symptoms of schizophrenia, and it exhibits antidepressant properties in patients with psychiatric disorders, dysthymia, and major depression.5 Amisulpride predominantly works in the limbic system, which explains its relatively lower risk of extrapyramidal adverse effects compared to other atypical antipsychotic agents.2,11 Oral tablets of amisulpride is used in European countries as a treatment for acute and chronic schizophrenic disorders, as well as secondary negative symptoms in mental health disorders such as affective disorders, depressive mood, and mental retardation.11

Amisulpride is also used as an antiemetic agent. In the US, the intravenous formulation of amisulpride is used to treat and prevent postoperative nausea and vomiting in adults, either as monotherapy or in combination with another antiemetic agent of a different drug class.10 It is marketed under the brand name Barhemsys.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 369.479
Monoisotopic: 369.172227057
Chemical Formula
C17H27N3O4S
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
  • Amisulpride
  • Amisulpridum

Pharmacology

Indication

Intravenous amisulpride is indicated in adults for the prevention of postoperative nausea and vomiting, either alone or in combination with an antiemetic of a different class. It is also indicated for the treatment of postoperative nausea and vomiting in patients who have received anti-emetic prophylaxis with an agent of a different class or have not received prophylaxis.10

Oral amisulpride is indicated for the treatment of acute and chronic schizophrenic disorders, characterized by positive symptoms with delusions, hallucinations, thought disorders, hostility and suspicious behavior; or primarily negative symptoms (deficit syndrome) with blunted affect, emotional and social withdrawal. Amisulpride also controls secondary negative symptoms in productive conditions as well as affective disorders such as depressive mood or retardation.11

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute schizophrenia••••••••••••••••••••• ••••••
Treatment ofChronic schizophrenia••••••••••••••••••••• ••••••
Treatment ofNegative symptom••••••••••••••••••••• ••••••
Treatment ofNegative symptom••••••••••••••••••••• ••••••
Treatment ofNegative symptom••••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Amisulpride is a selective dopamine D2 and D3 receptor antagonist with no affinity towards other dopamine receptor subtypes. Amisulpride is an atypical antipsychotic agent that works as an antagonist at dopamine receptors in the limbic system. Since it works preferentially in the limbic system, amisulpride is less likely to be associated with extrapyramidal adverse effects than other atypical antipsychotic agents. Amisulpride has no affinity for serotonin, alpha-adrenergic, H1-histamine, cholinergic, and sigma receptors. In clinical trials, amisulpride improved reduced secondary negative symptoms, affective symptoms, and psychomotor retardation in patients with acute exacerbation of schizophrenia. Notably, amisulpride has a differential target binding profile at different doses: at low doses, amisulpride selectively binds to presynaptic dopamine autoreceptors. At high doses, it preferentially binds to post-synaptic dopamine receptors.3 This explains how amisulpride reduces negative symptoms at low doses and mediates antipsychotic effects at high doses.11 One study alluded that the antinociceptive effects of amisulpride are mediated through opioid receptor acvitation and D2 receptor antagonism. 3,5 The actions of amisulpride at opioid receptors may explain its pro-convulsant properties.5

Amisulpride is also an antiemetic agent that prevents and alleviates postoperative nausea and vomiting. It primarily works by blocking dopamine signalling in the chemoreceptor trigger zone, which is a brain area that relays stimuli to the vomiting center.11

In clinical trials comprising Caucasian and Japanese subjects, amisulpride caused dose- and concentration-dependent prolongation of the QT interval; thus, intravenous infusion under a strict dosing regimen and close monitoring of patients with pre-existing cardiovascular conditions are recommended.10 Amisulpride increases plasma prolactin levels, leading to an association with benign pituitary tumours such as prolactinoma.11

Mechanism of action

Dopamine is an essential and critical neurotransmitter produced in the substantia nigra and ventral tegmental regions of the brain. Dopaminergic projection function in the nigrostriatal, mesolimbic, and mesocortical systems. Hyperactive dopamine transmission in the mesolimbic areas, or dopamine dysregulation in various major brain regions, is understood as the key driver of positive and negative symptoms of schizophrenia.9 Many antipsychotic agents act as D2 receptor antagonists, as with amisulpride.2 Amisulpride is a selective dopamine D2 and D3 receptor antagonist.10 It has high preferential activity towards dopamine receptors in the limbic system rather than the striatum, leading to a lower risk of extrapyramidal side effects than other atypical antipsychotic agents.4,6 At low doses, amisulpride reduces negative symptoms of schizophrenia by blocking pre-synaptic dopamine D2 and D3 receptors, increasing the levels of dopamine in the synaptic cleft and facilitating dopaminergic transmission.4 At higher doses, amisulpride blocks postsynaptic receptors, inhibiting dopaminergic hyperactivity: this explains the drug improving positive symptoms.1 Amisulpride also works as an antagonist at 5-HT7A receptors 8 and 5-HT2A receptors,4 which may be related to its antidepressant effects.5

The chemoreceptor trigger zone (CTZ), also commonly known as the area postrema (AP), is an important brain region located within the dorsal surface of the medulla oblongata. CTZ is involved in emesis: it contains receptors, such as dopamine receptors, that are activated in response to emetic agents in the blood and relay information to the vomiting center, which is responsible for inducing the vomiting reflex.7 Amisulpride is an antiemetic agent that works to limit signals that promote nausea and vomiting. Amisulpride binds to D2 and D3 receptors in the CTZ, leading to reduced dopaminergic signalling into the vomiting center.10

TargetActionsOrganism
A5-hydroxytryptamine receptor 7
antagonist
Humans
A5-hydroxytryptamine receptor 2A
antagonist
Humans
ADopamine D2 receptor
antagonist
Humans
ADopamine D3 receptor
antagonist
Humans
NMu-type opioid receptor
agonist
Humans
NDelta-type opioid receptor
agonist
Humans
NKappa-type opioid receptor
agonist
Humans
Absorption

Following oral administration, amisulpride is rapidly absorbed with absolute bioavailability of 48%.1 Amisulpride has two absorption peaks, with one rapidly achieved within one hour post-dose and a second peak occurring between three to four hours post-dose. Following oral administration of a 50 mg dose, two peak plasma concentrations were 39 ± 3 and 54 ± 4 ng/mL.11

Following intravenous administration, the peak plasma concentration of amisulpride is achieved at the end of the infusion period and the plasma concentration decreases by 50% within approximately 15 minutes. The AUC(0-∞) increases dose-proportionally in the dose range from 5 mg to 40 mg, which is about four times the maximum recommended dose. In healthy patients receiving intravenous amisulpride, the mean (SD) Cmax was 200 (139) ng/mL at the dose of 5 mg and 451 (230) ng/mL at the dose of 10 mg. The AUC ranged from 136 to 154 ng x h/mL in the dose range of 5 mg to 10 mg. In patients undergoing surgery, the mean (SD) Cmax ranged from 127 (62) to 161 (58) ng/mL at the dose of 5 mg. At the dose of 10 mg, it was 285 (446) ng/mL. The AUC ranged from 204 to 401 ng x h/mL.10

Volume of distribution

Following oral administration, the volume of distribution is 5.8 L/kg.11 Following intravenous infusion, the mean volume of distribution of amisulpride is estimated to be 127 to 144 L in surgical patients and 171 L in healthy subjects.10

Protein binding

Plasma protein binding ranges from 25% to 30% in the concentration range from 37 to 1850 ng/mL. Amisulpride distributes into erythrocytes.10

Metabolism

Amisulpride undergoes minimal metabolism 1 and its metabolites in plasma are largely undetectable. Two identified metabolites, formed by de-ethylation and oxidation, are pharmacologically inactive 6 and account for approximately 4% of the dose.11 Metabolites remain largely uncharacterized. Metabolism of amisulpride does not involve cytochrome P450 enzymes.10

Route of elimination

Following intravenous administration, about 74% of amisulpride is excreted in urine, where 58% of the recovered dose was excreted as unchanged amisulpride. About 23% of the dose is excreted in feces, with 20% of the excreted dose as unchanged parent drug. Following intravenous administration, about four metabolites were identified in urine and feces, accounting for less than 7% of the total dose administered.10 About 22 to 25% of orally administered amisulpride is excreted in urine, mostly as the unchanged parent drug.1

Half-life

Elimination is biphasic.6 The elimination half-life of amisulpride is approximately 12 hours after an oral dose.11 The mean elimination half-life is approximately four to five hours in both healthy subjects and patients undergoing surgery receiving intravenous amisulpride.10

Clearance

The plasma clearance of amisulpride is 20.6 L/h in surgical patients and 24.1 L/h in healthy subjects following intravenous administration. Renal clearance was estimated to be 20.5 L/hr (342 mL/min) in healthy subjects.10

Adverse Effects
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Toxicity

In mice, oral LD50 is 1024 mg/kg, intraperitoneal LD50 is 175 mg/kg, and subcutaneous LD50 is 224 mg/kg. The Lowest published toxic dose (TDLo) following subcutaneous administration is 0.24 mg/kg in rats. The oral TDLo in men is 4.3 mg/kg.12

Oral doses of amisulpride above 1200 mg/day are associated with adverse effects related to dopamine-2 (D2) antagonism. Cardiovascular adverse reactions include prolongation of the QT interval, torsades de pointes, bradycardia, and hypotension. Neuropsychiatric adverse reactions include sedation, coma, seizures, and dystonic and extrapyramidal reactions. As there is no specific antidote for amisulpride overdosage, management includes cardiac monitoring and treatment of severe extrapyramidal symptoms. Drug elimination with the use of hemodialysis is effective.10 Severe extrapyramidal effects may be managed with anticholinergic drugs.11

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Amisulpride is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Amisulpride is combined with Acenocoumarol.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Amisulpride.
AcetophenazineAcetophenazine may increase the antipsychotic activities of Amisulpride.
AcrivastineThe risk or severity of QTc prolongation can be increased when Amisulpride is combined with Acrivastine.
Food Interactions
  • Avoid alcohol. Amisulpride may enhance the effects of alcohol.
  • Take with or without food. A high fat meal does not significantly affect drug pharmacokinetics, although a carbohydrate rich meal decreases drug absorption and levels.

Products

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International/Other Brands
Deniban (Sanofi-Aventis) / Solian (Sanofi-Aventis)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BarhemsysInjection, solution2.5 mg/1mLIntravenousAcacia Pharma Ltd2020-02-27Not applicableUS flag

Categories

ATC Codes
N05AL05 — Amisulpride
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Aminobenzamides
Alternative Parents
Aminophenyl ethers / Methoxyanilines / Benzenesulfonyl compounds / Benzamides / Phenoxy compounds / Methoxybenzenes / Anisoles / Benzoyl derivatives / Alkyl aryl ethers / N-alkylpyrrolidines
show 9 more
Substituents
Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzamide / Aminophenyl ether / Aniline or substituted anilines / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzamide
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfone, benzamides, pyrrolidines, aromatic amine, aromatic amide (CHEBI:64045)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
8110R61I4U
CAS number
71675-85-9
InChI Key
NTJOBXMMWNYJFB-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

References

Synthesis Reference
US4401822
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. [Article]
  2. Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Curran MP, Perry CM: Amisulpride: a review of its use in the management of schizophrenia. Drugs. 2001;61(14):2123-50. doi: 10.2165/00003495-200161140-00014. [Article]
  7. MacDougall MR, Sharma S: Physiology, Chemoreceptor Trigger Zone . [Article]
  8. 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. [Article]
  9. Brisch R, Saniotis A, Wolf R, Bielau H, Bernstein HG, Steiner J, Bogerts B, Braun K, Jankowski Z, Kumaratilake J, Henneberg M, Gos T: The role of dopamine in schizophrenia from a neurobiological and evolutionary perspective: old fashioned, but still in vogue. Front Psychiatry. 2014 May 19;5:47. doi: 10.3389/fpsyt.2014.00047. eCollection 2014. [Article]
  10. FDA Approved Drug Products: BARHEMSYS (amisulpride) injection, for intravenous use [Link]
  11. Summary of Product Characteristics: Amisulpride Oral Tablets [Link]
  12. Cayman Chemical: Amisulpride Safety Data Sheet [Link]
Human Metabolome Database
HMDB0015633
KEGG Drug
D07310
PubChem Compound
2159
PubChem Substance
99443244
ChemSpider
2074
BindingDB
81790
RxNav
46303
ChEBI
64045
ChEMBL
CHEMBL243712
Therapeutic Targets Database
DAP000848
PharmGKB
PA162565877
Guide to Pharmacology
GtP Drug Page
Wikipedia
Amisulpride

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral100 MG
Tablet, film coatedOral400 MG
TabletOral
Tablet, film coatedOral
Tablet, coatedOral
Injection, solutionIntravenous2.5 mg/1mL
TabletOral400 MG
SolutionOral100 MG/ML
TabletOral200.000 mg
Tablet, coatedOral100 mg
Solution / drops100 mg/ml
Tablet, coatedOral400 mg
TabletOral50 mg
Tablet, film coatedOral100 mg
TabletOral200 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9545426No2017-01-172031-03-10US flag
US9084765No2015-07-212031-03-10US flag
US9889118No2018-02-132031-03-10US flag
US10525033No2020-01-072031-03-10US flag
US11357753No2018-02-092038-02-09US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)126-127https://www.pharmacopoeia.com/Catalogue/Preview?uri=%2Fcontent%2Ffile%2Fproducts%2Fhealthandsafety%2FCat_1143_GB.pdf
water solubilityInsolublehttps://www.pharmacopoeia.com/Catalogue/Preview?uri=%2Fcontent%2Ffile%2Fproducts%2Fhealthandsafety%2FCat_1143_GB.pdf
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)8.28Chemaxon
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002g-9054000000-b1dc7fa1718d7f3a0b9c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0609000000-2b372299b7870a4920eb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0009000000-99c1cc37ab9cf4683323
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0409000000-4e053b8ec1d55ced8499
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004l-0974000000-de9354d79437a4df60bc
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-01q9-0900000000-f91d53fb9c883bae9ca3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-324b93e2df83509f8048
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0009000000-99ab45809f8e56fbb616
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014l-0109000000-93205a0e84bbb061506a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-057i-0960000000-23d53c22f66a40ded55b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0509000000-de0803e7c69539424a4e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0019000000-7dec57b5001ab24504cc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0019000000-c532dacf370f0075220b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0092000000-6deb7fed54b4631e9813
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0005-0980000000-c78d2a361bbc674b41ce
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0005-0960000000-6a4706ff5588c4035137
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0190000000-e410c0158058e8740df0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-2237ffbc12b8e6459da5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0029000000-2143af7abc829fd8cacd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0290000000-bb210e691e1906ae74a7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0590000000-5f6a35609afc11e248ef
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0920000000-b89e4616edb7a54d2976
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-1900000000-15fd75a1097964a2b372
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-34c03de48e9e080e3c47
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0029000000-35268399499c0c04d5f5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0290000000-ad61214eeef71e97665b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0590000000-8322cbf2d5910eb0bd03
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0920000000-cbc60b473b3fb0de43ab
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-1900000000-c32487a90cfd10db9961
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0190000000-458205e2fa61496c6a54
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dl-2689000000-c4a31e81f70bf838ae8f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dl-0269000000-e2c8021fa5c019a7a29e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-72b725eb7eae2f0d9c42
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-d700f1cc1d4a060cf375
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-1529000000-8bd674eb29e947aa31f0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01tc-1269000000-2b468e6930123b706ba9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w4i-4951000000-892b46c388dd9a0933bf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-6498000000-64ef553aa6f66d5f7d95
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-202.0668392
predicted
DarkChem Lite v0.1.0
[M-H]-181.99512
predicted
DeepCCS 1.0 (2019)
[M+H]+203.4629392
predicted
DarkChem Lite v0.1.0
[M+H]+184.41965
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.7511392
predicted
DarkChem Lite v0.1.0
[M+Na]+191.94908
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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 ...
Gene Name
HTR7
Uniprot ID
P34969
Uniprot Name
5-hydroxytryptamine receptor 7
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
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. [Article]
  2. 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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
D(2) dopamine receptor
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. [Article]
  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. [Article]
  3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [Article]
  4. Xiberas X, Martinot JL, Mallet L, Artiges E, Canal M, Loc'h C, Maziere B, Paillere-Martinot ML: In vivo extrastriatal and striatal D2 dopamine receptor blockade by amisulpride in schizophrenia. J Clin Psychopharmacol. 2001 Apr;21(2):207-14. doi: 10.1097/00004714-200104000-00013. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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
Uniprot Name
D(3) dopamine receptor
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. [Article]
  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. [Article]
  3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [Article]
  4. Xiberas X, Martinot JL, Mallet L, Artiges E, Canal M, Loc'h C, Maziere B, Paillere-Martinot ML: In vivo extrastriatal and striatal D2 dopamine receptor blockade by amisulpride in schizophrenia. J Clin Psychopharmacol. 2001 Apr;21(2):207-14. doi: 10.1097/00004714-200104000-00013. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
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. [Article]
  2. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
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. [Article]
  2. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
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. [Article]
  2. 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. [Article]

Carriers

1. Erythrocyte
Kind
Group
Organism
Humans
Pharmacological action
No
Actions
Binder
Erythrocytes are also known as red blood cells.
References
  1. FDA Approved Drug Products: BARHEMSYS (amisulpride) injection, for intravenous use [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. FDA Approved Drug Products: BARHEMSYS (amisulpride) injection, for intravenous use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Drug transmembrane transporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name
SLC47A2
Uniprot ID
Q86VL8
Uniprot Name
Multidrug and toxin extrusion protein 2
Molecular Weight
65083.915 Da
References
  1. FDA Approved Drug Products: BARHEMSYS (amisulpride) injection, for intravenous use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA Approved Drug Products: BARHEMSYS (amisulpride) injection, for intravenous use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. FDA Approved Drug Products: BARHEMSYS (amisulpride) injection, for intravenous use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. FDA Approved Drug Products: BARHEMSYS (amisulpride) injection, for intravenous use [Link]

Drug created at March 19, 2008 16:22 / Updated at May 10, 2021 12:36