4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide

• ChemBase ID: 4427
• Molecular Formular: C17H27N3O4S
• Molecular Mass: 369.47898
• Monoisotopic Mass: 369.17222736
• SMILES: S(=O)(=O)(c1cc(C(=O)NCC2N(CCC2)CC)c(OC)cc1N)CC
• Canonical SMILES: CCN1CCCC1CNC(=O)c1cc(c(cc1OC)N)S(=O)(=O)CC
• 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)
• InChIKey: NTJOBXMMWNYJFB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
• IUPAC Traditional name: amisulpride; topral; 4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
• Brand Name: Solian; Deniban
• Synonyms: Socian; Sulamid; 4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide; DAN-2163; Deniban; Amisulpride; Solian; amisulpride; Aminosultopride; Amisulpride; Enorden; Majorem

Database IDs

• CAS Number: 53583-79-2; 71675-85-9
• EC Number: 275-831-7
• MDL Number: MFCD00866691
• PubChem SID: 99443244; 160967859; 24890689
• PubChem CID: 2159

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.032646
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.307408
• LogD (pH = 7.4): 0.090507895
• Log P: 0.2512877
• Molar Refractivity: 99.8448 cm^3
• Polarizability: 38.367462 Å^3
• Polar Surface Area: 101.73 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.5
• LOG S: -3.1
• Solubility (Water): 2.93e-01 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: white solid; White to Off-White Solid
• Melting Point: 126-127°C
• Hydrophobicity(logP): 1.10 [MANNHOLD,R ET AL. (1990)]

Safety Information

• Storage Condition: -20°C; -20°C Freezer; desiccated; protect from light
• RTECS: CV2308701
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Dopamine Receptor
• Mechanism of Action: Dopamine D 2 /D 3 -receptor antagonist; Spasmolytic

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Application(s): Antiemetic and spasmolytic agent; Antipsychotic; Neuroleptic agent; Psychotherapeutic (autism)
• Empirical Formula (Hill Notation): C17H27N3O4S

DETAILS

DrugBank - DB06288

• Drug Groups: approved; 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.
• Indication: Investigated for use/treatment in schizophrenia and schizoaffective disorders, mania in bipolar disorder, and depression.
• Toxicity: Overdoses of amisulpride have been linked with torsades de pointes.
• Affected Organisms: Humans and other mammals
• Absorption: Bioavailability is 48% following oral administration.
• Half Life: Approximately 12 hours
• Protein Binding: Low (17%)
• References: 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] ; Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. [Pubmed] ; 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] ; 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]
• External Links: Wikipedia

Selleck Chemicals - S1280

Research Area: Neurological Disease
Biological Activity:
Amisulpride is an atypical antipsychotic used to treat psychosis in schizophrenia and episodes of mania in bipolar disorder. In small doses it is also used to treat depression. Amisulpride functions primarily as a D2 and D3 receptor antagonist. It has high affinity for these receptors with dissociation constants of 2.8 nM and 3.2 nM, respectively. [1]References on Amisulpride[1] http://en.wikipedia.org/wiki/Amisulpride, ,

Sigma Aldrich - A2729

Biochem/physiol Actions
Amisulpride is a highly selective D2/D3 dopamine receptor antagonist and atypical antipsychotic.

Toronto Research Chemicals - A633250

Amisulpride is a neuroleptic agent, an analogue of Sulpiride (S689145). Amisulpride is used as an antipsychotic. Amisulpride is a dopamine receptor antagonist.

REFERENCES

• 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
• Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. Pubmed
• 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
• 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
• http://en.wikipedia.org/wiki/Amisulpride
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• De Winter, H.L. et al., Acta Cryst. C, 1990, 46, 313, (cryst struct)
• Mannhold, R. et al., Quant. Struct.-Act. Relat., 1990, 9, 21, (log P)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 565
• Noble, S. et al., CNS Drugs, 1999, 12, 471-483, (rev)
• Curran, M.P. et al., Drugs, 2001, 61, 2123-2150, (rev)