CAS 15676-16-1|N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide|5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-benzamide|N-1-(Ethylpyrrolidin-2-ylmethyl)-2-methoxy-5...

General Information

Structure

Molecular Formula

C₁₅H₂₃N₃O₄S

Molecular Mass

341.42582

Exact Mass

341.14092723

Charge

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

Canonic Smiles

CCN1CCCC1CNC(=O)c1cc(ccc1OC)S(=O)(=O)N

Isomeric Smiles

S(=O)(=O)(N)c1cc(C(=O)NCC2N(CCC2)CC)c(OC)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

-0.70

LogD (pH = 5.5)

-2.46

Log P

0.22

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.39

Polar Surface Area

101.73

Polarizability

35.61

Molar Refractivity

88.63

LOG S

-2.02

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

(±)-SULPIRIDEN-1-(Ethylpyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoylbenzamide5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-benzamide(±)-N-1-(乙基-2-吡咯基甲基)-2-甲氧基-5-氨磺酰苯甲酰胺(±)-N-1-(Ethylpyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoylbenzamide(±)-止呕灵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(±)-5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide(±)-SulpirideLevosulpiridum [INN-Latin]Levosulpirida [INN-Spanish]SulpyridSulpiridLevosulpirideSulpiridum [INN-Latin]Levosulpiride [INN]Sulpirida [INN-Spanish]DogmatilCoolspanDL-SulpirideAbilitMiradolN-(1-Ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamidobenzamiderac SulpirideEglonyl(+/-)-SulpirideDolmatilAiglonylMeresaDobrenGuastilMirbanilMisulvanDogmatylMilsulvanSulpirideSulpyrid(+-)-sulpirideN-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamidesulpirideN-((1-Ethyl-2-pyrrolidinyl)methyl)-2-methoxy-5-sulfamoylbenzamideSulpirid5-(Aminosulfonyl)-N-((1-ethyl-2-pyrrolidinyl)methyl)-2-methoxybenzamide

IUPAC Traditional name

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

Brand Name

ValiremNorestranKylistroDogmatylDolmatilEglonilSulpitilNormumStamonevrolSynedilNeogamaEglonylChampionylCoolspanDarletonEclorionPsicocenDesmenatEusulpidAiglonylDogmatilGuastilMariastelDobrenPyrkapplSursumidFidelanLevopraidPyrikapplLisopirideMeresaDresentOmperanLevobrenSernevinEquilidFardalanNufarolMisulvanCalmoflorineRestfulAbilitOmirylOzoderpinIsnamideZemorconAlimoralEnimonMirbanilTrilanSulprideSupriumMiradolSplotin

API Name

Sulpiride

International Nonproprietary Name (INN)

sulpiridesulpiridasulpiridum

Names and Identifiers

Registration numbers

EC Number

CAS Number

MDL Number

PubChem CID

PubChem SID

1609637374650485524277933135610211

Chemspider ID

5162

CHEMBL

26CHEMBL26

Unique Ingredient Identifier

Wikipedia Title

DrugBank ID

ATC CODE

IUPHAR ligand ID

KEGG ID

PubMed Citation Links

18985321200613452009166116327907199419572030450620305607208756761692446120538381179125011954625819370694196725802059991320177884179420351875773819864199

BKMS React Database

75628402635672495

BRENDA Database

4.1.1.283.6.5.51.3.1.224.2.1.1

BindingDB Database

11638

CHEBI ID

CHEBI:32168

BRENDA Ligand Database

NMRShiftDB Database

CompTox Database

Reactom Database

Reaxys Registry

MetaboLights Database

Patent number

LINCS Database

SureChEMBL Database

Drug Central Database

2,537

ACToR Database

15676-16-1

KEGG DRUG Database

D01226

Registration numbers

Properties

Physical Property

Solubility

2280 mg/L

H2O: slightly soluble

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble8.0 mg/mL

0.1 M HCl: soluble

ethanol: soluble

Hydrophobicity(logP)

0.6

Apperance

yellow powder

Product Information

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C15H23N3O4S

Pharmacology Properties

Admin Routes

Oral

Bioavailability

25–35%

Legal Status

Rx-only

Half Life

7 hours

Gene Information

human ... CA1(759), CA2(760), CA4(762), CA5A(763), CA5B(11238), CA9(768), DRD2(1813)

Mechanism of Action

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

Dopamine D2-receptor antagonist

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

MP Biomedicals

02153569

D2 Dopamine antagonist

Wikipedia

Sulpiride

Sigma Aldrich

S8010

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

TRC

S689145

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

ChEBI

CHEBI:32168

A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.

Molecule Details

References

PubChem Literature

From Data Sources

• Kramer, P., et al.: J. Neurosci., 31, 126 (2011)

• Alelyunas, Y., et al.: Bioorg. Med. Chem. Lett., 20, 7312, (2011)

• Miller, J.D. et al., Life Sci., 1987, 41, 1815, (pharmacol)

• Pitre, D. et al., Arch. Pharm. (Weinheim, Ger.), 1987, 320, 859, (phys props)

• Al-Koutayni-Rifai, M. et al., J. Labelled Compd. Radiopharm., 1989, 27, 811, (synth)

• Costall, B. et al., Psychopharmacologia, 1975, 43, 69, (pharmacol)

• Jenner, P. et al., Neuropharmacology, 1981, 20, 1285, (rev, activity)

• Ger. Pat., 1976, 2 365 832; CA, 85, 142976b, (synth)

• 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)

• 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)

• Serra, G. et al., Adv. Biosci. (Oxford), 1990, 77, 185, (rev, props)

• van de Waterbeemd, H. et al., Helv. Chim. Acta, 1981, 64, 2183, (cd, pharmacol)

• O'Connor, S.E. et al., Gen. Pharmacol., 1982, 13, 185, (rev, pharmacol)

• Maury, L. et al., Can. J. Chem., 1987, 65, 1613, (ir, struct)

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity