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...

General Information

Structure

Molecular Formula

C₁₇H₂₇N₃O₄S

Molecular Mass

369.47898

Exact Mass

369.17222736

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

-0.68

LogD (pH = 5.5)

-2.45

Log P

0.25

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.28

Polar Surface Area

101.73

Polarizability

39.63

Molar Refractivity

99.84

LOG S

-2.39

Data Source

Names and Identifiers

Synonyms

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

Brand Name

SolianDeniban

IUPAC Traditional name

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

IUPAC name

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

International Nonproprietary Name (INN)

amisulpridumamisulpridaamisulpride

Names and Identifiers

Registration numbers

CAS Number

71675-85-953583-79-2

PubChem SID

2489068916096785999443244135610697

EC Number

275-831-7

MDL Number

MFCD00866691

PubChem CID

2159

PubMed Citation Links

218221612185206022035899221218642188690521969105217467522184500622059694216637522164754522241281218886132117610822250612

SureChEMBL Database

Reactom Database

CompTox Database

KEGG DRUG Database

ACToR Database

Reaxys Registry

Wikipedia Title

CHEBI ID

Patent number

Drug Central Database

179

LINCS Database

LSM-1669

DrugBank ID

DB06288

MetaboLights Database

MTBLS2406MTBLS867

CHEMBL

CHEMBL243712

HMDB Database

HMDB0015633

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

1.10 [MANNHOLD,R ET AL. (1990)]

Apperance

white solid

White to Off-White Solid

Solubility

Dichloromethane

Chloroform

Melting Point

126-127°C

Pharmacology Properties

Dopamine Receptor

Spasmolytic

Dopamine D 2 /D 3 -receptor antagonist

Product Information

Safety Information

-20°C

protect from light

desiccated

-20°C Freezer

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

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

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

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

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

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

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

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

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

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

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

SolianDeniban

IUPAC Traditional name

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

IUPAC name

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

International Nonproprietary Name (INN)

amisulpridumamisulpridaamisulpride

Registration numbers

CAS Number

71675-85-953583-79-2

PubChem SID

2489068916096785999443244135610697

EC Number

275-831-7

MDL Number

MFCD00866691

PubChem CID

2159

PubMed Citation Links

218221612185206022035899221218642188690521969105217467522184500622059694216637522164754522241281218886132117610822250612

SureChEMBL Database

Reactom Database

CompTox Database

KEGG DRUG Database

ACToR Database

Reaxys Registry

Wikipedia Title

CHEBI ID

Patent number

Drug Central Database

179

LINCS Database

LSM-1669

DrugBank ID

DB06288

MetaboLights Database

CHEMBL

HMDB Database

Molecule Details

S1280

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

References

PubChem Literature

From Data Sources

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

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

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

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

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

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

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

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

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

• 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)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

1.10 [MANNHOLD,R ET AL. (1990)]

Apperance

white solid

White to Off-White Solid

Solubility

Dichloromethane

Chloroform

Melting Point

126-127°C

Pharmacology Properties

Dopamine Receptor

Spasmolytic

Dopamine D 2 /D 3 -receptor antagonist

Product Information

Safety Information

-20°C

protect from light

desiccated

-20°C Freezer

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Molecule

ID:4427