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

• ChemBase编号: 4427
• 分子式: C17H27N3O4S
• 平均质量: 369.47898
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
• IUPAC传统名: amisulpride; topral; 4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide
• 商标名: Solian; Deniban
• 别名: Socian; Sulamid; 4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide; DAN-2163; Deniban; Amisulpride; Solian; amisulpride; Aminosultopride; Amisulpride; Enorden; Majorem

登记号

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

理论计算性质

JChem

• Acid pKa: 14.032646
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -1.307408
• LogD (pH = 7.4): 0.090507895
• Log P: 0.2512877
• 摩尔折射率: 99.8448 cm^3
• 极化性: 38.367462 Å^3
• 极化表面积: 101.73 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.5
• LOG S: -3.1
• 溶解度: 2.93e-01 g/l

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane
• 外观: white solid; White to Off-White Solid
• 熔点: 126-127°C
• 疏水性(logP): 1.10 [MANNHOLD,R ET AL. (1990)]

安全信息

• 保存条件: -20°C; -20°C Freezer; desiccated; protect from light
• RTECS编号: CV2308701
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 22-24/25
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 作用靶点: Dopamine Receptor
• 生物活性机理: Dopamine D 2 /D 3 -receptor antagonist; Spasmolytic

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• 应用领域: Antiemetic and spasmolytic agent; Antipsychotic; Neuroleptic agent; Psychotherapeutic (autism)
• Empirical Formula (Hill Notation): C17H27N3O4S

详细说明

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.

参考文献

• 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)