CAS 71675-85-9|CAS 53583-79-2|Aminosultopride|Amisulpride|Solian|amisulpride|topral|Deniban|4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide|DAN-2163|4-Amino-N-[(1-et...

基本信息

化学结构

分子式

C₁₇H₂₇N₃O₄S

分子量

369.47898

精确质量

369.17222736

电荷

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

Canonic Smiles

CCN1CCCC1CNC(=O)c1cc(c(cc1OC)N)S(=O)(=O)CC

Isomeric Smiles

S(=O)(=O)(c1cc(C(=O)NCC2N(CCC2)CC)c(OC)cc1N)CC

计算属性

JChem

LogD (pH = 7.4)

-0.68

LogD (pH = 5.5)

-2.45

Log P

0.25

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

8.28

极化表面积

101.73

极化性

39.63

摩尔折射率

99.84

LOG S

-2.39

数据来源

名称和标识

别名

AminosultoprideAmisulprideamisulprideAmisulpride4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamideDAN-2163DenibanSolianEnordenSocianMajoremSulamid4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-o-anisamideAminosultoprideamisulpride

商标名

SolianDeniban

IUPAC传统名

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

IUPAC标准名

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

国际非专利药品(INN)

amisulpridumamisulpridaamisulpride

名称和标识

数据登录号

化合物性质

理化性质

药理学性质

作用靶点

Dopamine Receptor

生物活性机理

Spasmolytic

Dopamine D 2 /D 3 -receptor antagonist

产品相关信息

成盐信息

Free Base

Empirical Formula (Hill Notation)

C17H27N3O4S

纯度

≥98% (HPLC)

质检报告

下载链接

应用领域

Psychotherapeutic (autism)

Neuroleptic agent

Antiemetic and spasmolytic agent

Antipsychotic

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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, ,

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]

Sigma Aldrich

A2729

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

TRC

A633250

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

ChEBI

CHEBI:64045

A member of the class of benzamides resulting from the formal condensation of the carboxy group of 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid with the primary amino group of 2-(aminomethyl)-1-ethylpyrrolidine. It is a potent, selective dopamine D2 and D3 receptor antagonist. It is an atypical antipsychotic/antischizophrenic agent with limited extrapyrimidal side effects.

描述信息

参考文献

PubChem文献

数据源提供

• 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

• Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. Pubmed

• http://en.wikipedia.org/wiki/Amisulpride

• Perrault, G., et al.: J. Pharmacol. Exp. Ther., 280, 73 (1985)

• Protais, P., et al.: Neuropharmacol., 24, 861 (1985)

• De Winter, H.L. et al., Acta Cryst. C, 1990, 46, 313, (cryst struct)

• Curran, M.P. et al., Drugs, 2001, 61, 2123-2150, (rev)

• Hanocq, M. et al., Pharm. Acta Helv., 1982, 57, 37, (uv, ir)

• Bohbot, M. et al., J. Chromatogr., 1987, 416, 414, (hplc)

• Mannhold, R. et al., Quant. Struct.-Act. Relat., 1990, 9, 21, (log P)

• U.S. Pat., 1979, 4 294 828; CA, 91, 211113f, (synth, pharmacol)

• Noble, S. et al., CNS Drugs, 1999, 12, 471-483, (rev)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 565

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

商标名

SolianDeniban

IUPAC传统名

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

IUPAC标准名

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

国际非专利药品(INN)

amisulpridumamisulpridaamisulpride

描述信息

Selleck Chemicals

S1280

DrugBank

DB06288

Drug Groups

approved; investigational

Description

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

• Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. [Pubmed]

External Links

• [Wikipedia]

Sigma Aldrich

A2729

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

TRC

A633250

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

ChEBI

CHEBI:64045

参考文献

PubChem文献

数据源提供

• 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

• Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. Pubmed

• http://en.wikipedia.org/wiki/Amisulpride

• Perrault, G., et al.: J. Pharmacol. Exp. Ther., 280, 73 (1985)

• Protais, P., et al.: Neuropharmacol., 24, 861 (1985)

• De Winter, H.L. et al., Acta Cryst. C, 1990, 46, 313, (cryst struct)

• Curran, M.P. et al., Drugs, 2001, 61, 2123-2150, (rev)

• Hanocq, M. et al., Pharm. Acta Helv., 1982, 57, 37, (uv, ir)

• Bohbot, M. et al., J. Chromatogr., 1987, 416, 414, (hplc)

• Mannhold, R. et al., Quant. Struct.-Act. Relat., 1990, 9, 21, (log P)

• U.S. Pat., 1979, 4 294 828; CA, 91, 211113f, (synth, pharmacol)

• Noble, S. et al., CNS Drugs, 1999, 12, 471-483, (rev)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 565

生物活性

PubChem BioAssay

化合物性质

理化性质

药理学性质

作用靶点

Dopamine Receptor

生物活性机理

Spasmolytic

Dopamine D 2 /D 3 -receptor antagonist

产品相关信息

成盐信息

Free Base

Empirical Formula (Hill Notation)

C17H27N3O4S

纯度

≥98% (HPLC)

质检报告

下载链接

应用领域

Psychotherapeutic (autism)

Neuroleptic agent

Antiemetic and spasmolytic agent

Antipsychotic

化合物信息

ID:4427