N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide

• ChemBase编号: 274
• 分子式: C15H23N3O4S
• 平均质量: 341.42582
• 单一同位素质量: 341.14092723
• SMILES: S(=O)(=O)(N)c1cc(C(=O)NCC2N(CCC2)CC)c(OC)cc1
• Canonical SMILES: CCN1CCCC1CNC(=O)c1cc(ccc1OC)S(=O)(=O)N
• InChI: InChI=1S/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)
• InChIKey: BGRJTUBHPOOWDU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide
• IUPAC传统名: N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide; @sulpiride; sulpiride
• 商标名: Coolspan; Darleton; Desmenat; Dobren; Dogmatil; Dogmatyl; Dolmatil; Dresent; Eclorion; Eglonil; Eglonyl; Enimon; Equilid; Eusulpid; Fardalan; Fidelan; Guastil; Isnamide; Kylistro; Levobren; Levopraid; Lisopiride; Mariastel; Meresa; Miradol; Mirbanil; Misulvan; Neogama; Norestran; Normum; Nufarol; Omiryl; Omperan; Ozoderpin; Psicocen; Pyrikappl; Pyrkappl; Restful; Sernevin; Splotin; Stamonevrol; Sulpitil; Sulpride; Suprium; Sursumid; Synedil; Trilan; Valirem; Zemorcon; Abilit; Aiglonyl; Alimoral; Calmoflorine; Championyl
• 别名: (±)-5-氨基磺酰基-N-[(1-乙基-2-吡咯烷基)甲基]-2-甲氧基苯甲酰胺; (±)-N-1-(乙基-2-吡咯基甲基)-2-甲氧基-5-氨磺酰苯甲酰胺; (±)-止呕灵; Milsulvan; Sulpiride; Levosulpirida [INN-Spanish]; Levosulpiride; Levosulpiride [INN]; Levosulpiridum [INN-Latin]; Sulpirida [INN-Spanish]; Sulpiridum [INN-Latin]; Sulpirid; Sulpyrid; Sulpiride; 5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-benzamide; N-1-(Ethylpyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoylbenzamide; (±)-SULPIRIDE; (±)-5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide; (±)-N-1-(Ethylpyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoylbenzamide; (±)-Sulpiride; N-(1-Ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamidobenzamide; (+/-)-Sulpiride; Abilit; Aiglonyl; Coolspan; DL-Sulpiride; Dobren; Dogmatil; Dogmatyl; Dolmatil; Eglonyl; Guastil; Meresa; Miradol; Mirbanil; Misulvan; rac Sulpiride

登记号

• CAS号: 15676-16-1
• EC号: 239-753-7
• MDL号: MFCD00055061
• PubChem SID: 24277933; 46504855; 160963737
• PubChem CID: 5355
• ATC码: N05AL01
• CHEMBL: 26
• Chemspider ID: 5162
• DrugBank ID: DB00391
• IUPHAR配体索引: 5501
• KEGG ID: D01226
• 美国药典/FDA物质标识码: 7MNE9M8287
• 维基百科标题: Sulpiride

理论计算性质

JChem

• Acid pKa: 10.239752
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): -2.4638896
• LogD (pH = 7.4): -0.7005867
• Log P: 0.21877044
• 摩尔折射率: 88.6331 cm^3
• 极化性: 34.695236 Å^3
• 极化表面积: 101.73 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.2
• LOG S: -2.8
• 溶解度: 5.37e-01 g/l

分子性质

理化性质

• 溶解度: 0.1 M HCl: soluble; 2280 mg/L; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble8.0 mg/mL; ethanol: soluble; H2O: slightly soluble
• 外观: yellow powder
• 疏水性(logP): 0.6

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: BZ3400000
• 德国WGK号: 2
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral
• 生物利用度: 25–35%
• 半衰期: 7 hours
• 法定药品分级: Rx-only
• 相关基因信息: human ... CA1(759), CA2(760), CA4(762), CA5A(763), CA5B(11238), CA9(768), DRD2(1813)
• 生物活性机理: Dopamine D2-receptor antagonist; In contrast to most other neuroleptics which block both dopamine D1 and D2 receptors, Sulpiride is more selective and acts primarily as a dopamine D2 antagonist; Sulpiride appears to lack effects on norepinephrine, acetylcholine, serotonin, histamine, or gamma-aminobutyric acid (GABA) receptors

产品相关信息

• 应用领域: Antianxiety drug; Antidepressant; Digestive aid; Low acute toxicity; Migraine therapeutic; Non-sedative major antipsychotic agent
• Empirical Formula (Hill Notation): C15H23N3O4S

详细说明

MP Biomedicals - 02153569

D2 Dopamine antagonist

DrugBank - DB00391

• Drug Groups: approved
• Description: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed)
• Indication: Sulpiride is indicated for the treatment of schizophrenia.
• Pharmacology: Sulpiride is a substituted benzamide derivative and a selective dopamine D2 antagonist with antipsychotic and antidepressant activity. Other benzamide derivatives include metoclopramide, tiapride, and sultopride.
• Toxicity: Sulpiride has a relatively low order of acute toxicity. Substantial amounts may cause severe but reversible dystonic crises with torticollis, protrusion of the tongue, and/or trism. In some cases all the classical symptoms typical of severe Parkinson's Disease may be noted; in others, over-sedation/coma may occur.
• Affected Organisms: Humans and other mammals
• Absorption: Sulpiride is absorbed slowly from the gastrointestinal tract. Its oral bioavailability is only 25 to 35% with marked interindividual differences.
• Half Life: 6 to 8 hours
• External Links: Wikipedia

Sigma Aldrich - S8010

Biochem/physiol Actions
D2 dopamine receptor antagonist; antipsychotic.
Reconstitution
Solutions may be stored for several days at 4 °C.

Toronto Research Chemicals - S689145

An antipsychotic drug used in the treatment of Schozophrenia and depression.

参考文献

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