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

• ChemBase ID: 274
• Molecular Formular: C15H23N3O4S
• Molecular Mass: 341.42582
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide
• IUPAC Traditional name: N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide; @sulpiride; sulpiride
• Brand Name: 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
• Synonyms: 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; (±)-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

Database IDs

• CAS Number: 15676-16-1
• EC Number: 239-753-7
• MDL Number: MFCD00055061
• PubChem SID: 160963737; 24277933; 46504855
• PubChem CID: 5355
• ATC CODE: N05AL01
• CHEMBL: 26
• Chemspider ID: 5162
• DrugBank ID: DB00391
• IUPHAR ligand ID: 5501
• KEGG ID: D01226
• Unique Ingredient Identifier: 7MNE9M8287
• Wikipedia Title: Sulpiride

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.239752
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.4638896
• LogD (pH = 7.4): -0.7005867
• Log P: 0.21877044
• Molar Refractivity: 88.6331 cm^3
• Polarizability: 34.695236 Å^3
• Polar Surface Area: 101.73 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.2
• LOG S: -2.8
• Solubility (Water): 5.37e-01 g/l

PROPERTIES

Physical Property

• Solubility: 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
• Apperance: yellow powder
• Hydrophobicity(logP): 0.6

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: BZ3400000
• German water hazard class: 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 25–35%
• Half Life: 7 hours
• Legal Status: Rx-only
• Gene Information: human ... CA1(759), CA2(760), CA4(762), CA5A(763), CA5B(11238), CA9(768), DRD2(1813)
• Mechanism of Action: 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

Product Information

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

DETAILS

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.

REFERENCES

• Kramer, P., et al.: J. Neurosci., 31, 126 (2011)
• Alelyunas, Y., et al.: Bioorg. Med. Chem. Lett., 20, 7312, (2011)
• Costall, B. et al., Psychopharmacologia, 1975, 43, 69, (pharmacol)
• Ger. Pat., 1976, 2 365 832; CA, 85, 142976b, (synth)
• van de Waterbeemd, H. et al., Helv. Chim. Acta, 1981, 64, 2183, (cd, pharmacol)
• Jenner, P. et al., Neuropharmacology, 1981, 20, 1285, (rev, activity)
• Ma, L.Y.Y. et al., Acta Cryst. B, 1982, 38, 2861, (cryst struct, abs config, bibl)
• Montanaro, N. et al., Adv. Biochem. Psychopharmacol., 1982, 31, 341, (activity)
• O'Connor, S.E. et al., Gen. Pharmacol., 1982, 13, 185, (rev, pharmacol)
• Pitre, D. et al., Arch. Pharm. (Weinheim, Ger.), 1987, 320, 859, (phys props)
• Maury, L. et al., Can. J. Chem., 1987, 65, 1613, (ir, struct)
• Miller, J.D. et al., Life Sci., 1987, 41, 1815, (pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3746
• Pitre, D. et al., Anal. Profiles Drug Subst., 1988, 17, 607, (rev)
• Al-Koutayni-Rifai, M. et al., J. Labelled Compd. Radiopharm., 1989, 27, 811, (synth)
• Serra, G. et al., Adv. Biosci. (Oxford), 1990, 77, 185, (rev, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 615
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EPD500