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! Molecular target !! Binding Affinity (K<sub>i</sub> in nM)<ref>{{cite web|last=National Institute of Mental Health|title=PDSP Ki Database|url=http://pdsp.med.unc.edu/pdsp.php|publisher=University of North Carolina|accessdate=5 July 2013}}</ref>
! Molecular target !! Binding Affinity (K<sub>i</sub> in nM)<ref>{{cite web|last=National Institute of Mental Health |title=PDSP Ki Database |url=http://pdsp.med.unc.edu/pdsp.php |publisher=University of North Carolina |accessdate=5 July 2013 |deadurl=yes |archiveurl=https://web.archive.org/web/20131108013656/http://pdsp.med.unc.edu/pdsp.php |archivedate=8 November 2013 |df= }}</ref>
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| [[Serotonin transporter|SERT]] || >10000
| [[Serotonin transporter|SERT]] || >10000

Revision as of 19:13, 11 October 2016

Amisulpride
Clinical data
Trade namesSolian
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: C
Routes of
administration		Oral, IV
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability48%[1][2]
Protein binding16%[2]
MetabolismHepatic (minimal; most excreted unchanged)[2]
Elimination half-life12 hours[1]
ExcretionRenal[1] (23–46%),[3][4] Fecal[2]
Identifiers
  • 4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.068.916 Edit this at Wikidata
Chemical and physical data
FormulaC17H27N3O4S
Molar mass369.48 g/mol g·mol−1
3D model (JSmol)
  • O=S(=O)(c1cc(c(OC)cc1N)C(=O)NCC2N(CC)CCC2)CC
  • 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) checkY
  • Key:NTJOBXMMWNYJFB-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Amisulpride (sold as Amazeo, Amipride (AU), Amival, Solian (AU, IE, RU, UK, ZA), Soltus, Sulpitac (IN), Sulprix (AU), Socian (BR), is an atypical antipsychotic used to treat psychosis in schizophrenia and episodes of mania in bipolar disorder. In Italy, it is also used as a treatment for dysthymia.[5]

It was introduced by Sanofi-Aventis in the 1990s. Its patent had expired by 2008 and hence generic formulations are now available.[6]

Medical Uses

Schizophrenia

It appears to have comparable efficacy to olanzapine in the treatment of schizophrenia.[7][8][9] Amisulpride augmentation, similarly to sulpiride augmentation, has been considered a viable treatment option (although, it is worth noting that the supporting evidence is limited to the theory, case reports, a small randomised double-blind placebo-controlled trial[10] and a couple of open-label studies[11][12]) in clozapine-resistant cases of schizophrenia.[13][14] A randomised, double-blind, placebo-controlled clinical trial has been conducted to evaluate the efficacy of celecoxib as an adjunct to amisulpride, with significant success.[15] Another recent study concluded that amisulpride is an appropriate first-line treatment for the management of acute psychosis.[16]

Bipolar disorder

Amisulpride has been tried as a treatment for acute mania in a few open-label studies.[17][18] These findings should be interpreted with caution, not just due to the fact that these clinical trials were all open-label and hence low-quality but also because several case reports have been made documenting the precipitation of mania in schizophrenia patients that received amisulpride.[2][19]

Dysthymia

At low doses, it is also used to treat dysthymia where it appears to be at least as effective as conventional antidepressants according to a recent Cochrane review. Studies showed that at dose < 50 mg amisulpride has preferential affinity for pre-synaptic dopamine D2 and D3 autoreceptor subtypes (pre-synaptics autoreceptors serves as a negative feedback loop control). By blocking these autoreceptors amisulpride is preventing neurons to stop firing dopamine, leading to an increase of dopamine concentration in the brain. This mode of action could explain its strong antidepressant properties.[4][20][5] In this indication, amisulpride is significantly more effective than:

and equal to:

Investigational

Low-dose amisulpride has been found to be an effective treatment for postoperative emesis in a recent randomised, double-blind, placebo-controlled clinical trial.[25] In a small (N=11) clinical trial amisulpride combined with either mirtazapine or citalopram was found an effective treatment for psychotic depression in elderly patients, although it should be noted that this trial was not placebo-controlled and hence the level of evidence it provides to amisulpride's efficacy in this indication is low.[26] In a medium-sized (N=106) single-blind study it was found efficacious and well-tolerated in improving depressive symptoms in cancer patients undergoing chemotherapy.[27]

Adverse effects

Very Common (≥10% incidence)[28]
  • Extrapyramidal side effects (EPS; including dystonia, tremor, akathisia, parkinsonism). Produces a moderate degree of EPS; more than aripiprazole (not significantly, however), clozapine, iloperidone (not significantly), olanzapine (not significantly), quetiapine (not significantly) and sertindole; less than chlorpromazine (not significantly), haloperidol, lurasidone (not significantly), paliperidone (not significantly), risperidone (not significantly), ziprasidone (not significantly) and zotepine (not significantly).[9]
Common (≥1%, <10% incidence)[2][29][30][31]
  • Hyperprolactinaemia (which can lead to galactorrhoea, breast enlargement and tenderness, sexual dysfunction, etc.)
  • Weight gain (produces less weight gain than chlorpromazine, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zotepine and more (although not statistically significantly) weight gain than haloperidol, lurasidone, ziprasidone and approximately as much weight gain as aripiprazole and asenapine)[9]
  • Anticholinergic side effects (although it does not bind to the muscarinic acetylcholine receptors and hence these side effects are usually quite mild) such as
- constipation
- dry mouth
- disorder of accommodation
- Blurred vision
Rare (<1% incidence)[2][29][30][31]


Hyperprolactinaemia results from antagonism of the D2 receptors located on the lactotrophic cells found in the anterior pituitary gland. Amisulpride has a high propensity for elevating plasma prolactin levels as a result of its poor blood-brain barrier penetrability and hence the resulting greater ratio of peripheral D2 occupancy to central D2 occupancy. This means that to achieve the sufficient occupancy (~60–80%[32]) of the central D2 receptors in order to elicit its therapeutic effects a dose must be given that is enough to saturate peripheral D2 receptors including those in the anterior pituitary.[33][34]

  • Somnolence. It produces minimal sedation due to its absence of cholinergic, histaminergic and alpha adrenergic receptor antagonism. It is one of the least sedating antipsychotics.[9]

Contraindications

Amisulpride's use is contraindicated in the following disease states[2][30][31]

Neither is it recommended to use amisulpride in patients with hypersensitivities to amisulpride or the excipients found in its dosage form.[2]

Interactions

Amisulpride should not be used in conjunction with drugs that prolong the QT interval (such as citalopram, venlafaxine, bupropion, clozapine, tricyclic antidepressants, sertindole, ziprasidone, etc.),[35] reduce heart rate and those that can induce hypokalaemia. Likewise it is imprudent to combine antipsychotics due to the additive risk for tardive dyskinesia and neuroleptic malignant syndrome.[35]

Overdose

Torsades de pointes is common in overdose.[36][37] Amisulpride is moderately dangerous in overdose (with the TCAs being very dangerous and the SSRIs being modestly dangerous).[35][38]

Pharmacology

Amisulpride function primarily as a D2 and D3 receptor antagonist. It has high affinity for these receptors with dissociation constants of 2.2 nM and 2.4 nM, respectively. Although standard doses used to treat psychosis inhibit dopaminergic neurotransmission, low doses preferentially block inhibitory pre-synaptic autoreceptors. This results in a facilitation of dopamine activity, and for this reason, low dose amisulpride has also been used to treat dysthymia.[2]

Amisulpride and its relative sulpiride have been shown to bind to and activate the GHB receptor at doses that are used for therapeutic purposes.[39]

Though it has long been widely assumed that dopaminergic modulation is solely responsible for the respective antidepressant and antipsychotic properties of amisulpride, it has recently been shown that it also acts as a potent antagonist at the 5-HT7 receptor.[40] Several of the other atypical antipsychotics such as risperidone and ziprasidone are potent antagonists at the 5-HT7 receptor as well, and selective antagonists of the receptor show antidepressant properties themselves. To characterize the role of the 5-HT7 receptor in the antidepressant effects of amisulpride, a study prepared 5-HT7 receptor knockout mice.[40] The study found that in two widely used rodent models of depression, the tail suspension test, and the forced swim test, those mice did not exhibit an antidepressant response upon treatment with amisulpride.[40] These results suggest that 5-HT7 receptor antagonism mediates the antidepressant effects of amisulpride.[40]

Amisulpride also appears to bind with high affinity to the 5-HT2B receptor (see below table), though the clinical implications of this, if any, are unclear.

Molecular target Binding Affinity (Ki in nM)[41]
SERT >10000
NET >10000
DAT >10000
5-HT1A >10000
5-HT1B 1744
5-HT1D 1341
5-HT1E >10000
5-HT2A 8304
5-HT2B 13
5-HT2C >10000
5-HT3 >10000
5-HT5A >10000
5-HT6 4154
5-HT7 11.5[40]
α1A >10000
α1B >10000
α1D >10000
α2A 1114
α2C 1540
β1 >10000
β2 >10000
β3 >10000
M1 >10000
M2 >10000
M3 >10000
M4 >10000
M5 >10000
D1 >10000
D2 2.2
D3 2.4
D4 2370
D5 >10000
H1 >10000
H2 >10000
H4 >10000
δ opioid >10000
κ opioid >10000
μ opioid >10000
Prostaglandin E3 receptor >10000
Prostaglandin E4 receptor >10000

Availability

Amisulpride is not approved by the Food and Drug Administration for use in the United States, but it is used in Europe (France, Germany, Italy, Switzerland, Russia, United Kingdom, etc.), Israel, India, New Zealand and Australia (TGA approved in February 2002[2]) to treat psychosis and schizophrenia.[42][43]

Synthesis

Dopamine receptor antagonist.

Amisulpride synthesis: M. Thominet et al., BE 872585 ; eidem, U.S. patent 4,401,822 (1979, 1983 both to Soc. d'Etudes Sci. Ind. de l'Ile-de-France).

4-amino-5-mercapto-2-methoxybenzoic acid (1) is alkylated with diethyl sulfate to 4-amino-5-(ethylthio)-2-methoxybenzoic acid (2) and then this is oxidized with H2O2 to 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid (3). A mixed anhydride is prepared via reaction with ethyl chloroformate (4) and then amidation with 1-ethyl-(2-aminoethyl)pyrrolidine (5) to give amisulpride as the product (6).

See also

References

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  2. ^ a b c d e f g h i j k "PRODUCT INFORMATION SOLIAN® TABLETS and SOLUTION" (PDF). TGA eBusiness Services. Sanofi-Aventis Australia Pty Ltd. 9 September 2013. Retrieved 17 October 2013.
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