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53583-79-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:4427 http://www.chembase.cn/molecule-4427.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
53583-79-2
71675-85-9
EC Number
275-831-7
MDL Number
MFCD00866691
PubChem SID
160967859
99443244
24890689
PubChem CID
2159

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.032646  H Acceptors
H Donor LogD (pH = 5.5) -1.307408 
LogD (pH = 7.4) 0.090507895  Log P 0.2512877 
Molar Refractivity 99.8448 cm3 Polarizability 38.367462 Å3
Polar Surface Area 101.73 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.5  LOG S -3.1 
Solubility (Water) 2.93e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Apperance
white solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
126-127°C expand Show data source
Hydrophobicity(logP)
1.10 [MANNHOLD,R ET AL. (1990)] expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
desiccated expand Show data source
protect from light expand Show data source
RTECS
CV2308701 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
Safety Statements
22-24/25 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Dopamine Receptor expand Show data source
Mechanism of Action
Dopamine D 2 /D 3 -receptor antagonist expand Show data source
Spasmolytic expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiemetic and spasmolytic agent expand Show data source
Antipsychotic expand Show data source
Neuroleptic agent expand Show data source
Psychotherapeutic (autism) expand Show data source
Empirical Formula (Hill Notation)
C17H27N3O4S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB06288 external link
Item Information
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 external link
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 external link
Biochem/physiol Actions
Amisulpride is a highly selective D2/D3 dopamine receptor antagonist and atypical antipsychotic.
Toronto Research Chemicals - A633250 external link
Amisulpride is a neuroleptic agent, an analogue of Sulpiride (S689145). Amisulpride is used as an antipsychotic. Amisulpride is a dopamine receptor antagonist.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • Protais, P., et al.: Neuropharmacol., 24, 861 (1985)
  • • Perrault, G., et al.: J. Pharmacol. Exp. Ther., 280, 73 (1985)
  • • U.S. Pat., 1979, 4 294 828; CA, 91, 211113f, (synth, pharmacol)
  • • Hanocq, M. et al., Pharm. Acta Helv., 1982, 57, 37, (uv, ir)
  • • Bohbot, M. et al., J. Chromatogr., 1987, 416, 414, (hplc)
  • • 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)
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PATENTS

PATENTS

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