Structure via PubChem · Public domain (PubChem)
(RS)-amisulpride
Sign in to saveAlso known as (±)-amisulpride, 4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-o-anisamide, 4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl]-2-methoxybenzamide, aminosultopride, Solian
Amisulpride, sold under the brand names Socian and Barhemsys, is a medication used in the treatment of schizophrenia, acute psychotic episodes, depression, and nausea and vomiting. It is specifically used at lower doses intravenously to prevent and treat postoperative nausea and vomiting, at low doses by mouth to treat depression, and at higher doses by mouth to treat psychosis.
Key facts
- Drug.C
- 17
- Drug.H
- 27
- Drug.N
- 3
- Drug.O
- 4
- Drug.S
- 1
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 456689148
- Drug.image
- Amisulpride.enantiomers_labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300px
- Drug.imageL
- (S)-amisulpride ball-and-stick model from xtal 1990.png
- Drug.image_classL
- bg-transparent
- Drug.widthL
- 150px
- Drug.imageR
- (R)-amisulpride ball-and-stick model from xtal 2017.png
- Drug.image_classR
- bg-transparent
- Drug.widthR
- 150px
- Drug.tradename
- Socian, Barhemsys, others
via Wikipedia infobox
Chemical data
- Formula
- C17H27N3O4S
- Molecular weight
- 369.5 g/mol
- IUPAC name
- 4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide
- SMILES
- CCN1CCCC1CNC(=O)C2=CC(=C(C=C2OC)N)S(=O)(=O)CC
- InChIKey
- NTJOBXMMWNYJFB-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 110 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
2 papers- Effect of the amisulpride isomers on rat catalepsy.European journal of pharmacology · 2002
- Discriminative stimulus properties of the atypical antipsychotic amisulpride: comparison to its isomers and to other benzamide derivatives, antipsychotic, antidepressant, and antianxiety drugs in C57BL/6 mice.Psychopharmacology · 2017
via PubMed
~16 min read
Encyclopedic overview
26 sectionsContents
- Medical uses
- Schizophrenia
- Depression
- Postoperative nausea and vomiting
- Available forms
- Contraindications
- Adverse effects
- Discontinuation
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- United States clinical development
- {{anchor|Society and culture}}Society and culture
- Brand names
- Availability
- Research
- Bipolar depression
- Chemotherapy-induced nausea and vomiting
- Chemical derivatives
- See also
- References
- External links
Amisulpride, sold under the brand names Socian and Barhemsys, is a medication used in the treatment of schizophrenia, acute psychotic episodes, depression, and nausea and vomiting. It is specifically used at lower doses intravenously to prevent and treat postoperative nausea and vomiting, at low doses by mouth to treat depression, and at higher doses by mouth to treat psychosis.
It is usually classed with the atypical antipsychotics. Chemically it is a benzamide and like other benzamide antipsychotics, such as sulpiride, it is associated with a high risk of elevating blood levels of the lactation hormone, prolactin (thereby potentially causing the absence of the menstrual cycle, breast enlargement, even in males, breast milk secretion not related to breastfeeding, impaired fertility, impotence, breast pain, etc.), and a low risk, relative to the typical antipsychotics, of causing movement disorders.
Excerpted from Wikipedia’s “(RS)-amisulpride” article, available under the CC BY-SA 4.0 licence.