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Details

Stereochemistry RACEMIC
Molecular Formula C15H23N3O4S
Molecular Weight 341.426
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULPIRIDE

SMILES

CCN1CCCC1CNC(=O)C2=C(OC)C=CC(=C2)S(N)(=O)=O

InChI

InChIKey=BGRJTUBHPOOWDU-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H23N3O4S
Molecular Weight 341.426
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/6628519

Sulpiride is an atypical antipsychotic drug (although some texts have referred to it as a typical antipsychotic) of the benzamide class used mainly in the treatment of psychosis associated with schizophrenia and major depressive disorder, and sometimes used in low dosage to treat anxiety and mild depression. Sulpiride is commonly used in Europe, Russia and Japan. Sulpiride is a selective antagonist at dopamine D2 and D3 receptors. This action dominates in doses exceeding 600 mg daily. In doses of 600 to 1,600 mg sulpiride shows mild sedating and antipsychotic activity. Its antipsychotic potency compared to chlorpromazine is only 0.2 (1/5). In low doses (in particular 50 to 200 mg daily) its prominent feature is antagonism of presynaptic inhibitory dopamine receptors accounting for some antidepressant activity and a stimulating effect. Therefore, it is in these doses used as a second line antidepressant. Racemic and L-sulpiride significantly decreased stimulated serum gastrin concentration, but they did not affect fasting serum gastrin or basal and stimulated gastric acidity. D-sulpiride significantly decreased gastric acid secretion, without affecting serum gastrin levels.

Originator

Sources: Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles (1967), 265, (17), 1253-4

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.28 nM [IC50]
66.22 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Eglonyl

Approved Use

Indications. Acute and chronic psychosis (confusion, delirium, confusion, agrammatism, abulia), schizophrenia; neurotic state, accompanied by lethargy; psychosomatic symptoms (especially for stomach ulcers and duodenal ulcers and hemorrhagic rektokolite).
Primary
Eglonyl

Approved Use

Indications. Acute and chronic psychosis (confusion, delirium, confusion, agrammatism, abulia), schizophrenia; neurotic state, accompanied by lethargy; psychosomatic symptoms (especially for stomach ulcers and duodenal ulcers and hemorrhagic rektokolite).
PubMed

PubMed

TitleDatePubMed
Nicotine potentiates sulpiride-induced catalepsy in mice.
1998
Drug-induced motor complications in dopa-responsive dystonia: implications for the pathogenesis of dyskinesias and motor fluctuations.
1999 Jul-Aug
D1 receptor blockade improves L-dopa-induced dyskinesia but worsens parkinsonism in MPTP monkeys.
1999 Mar 10
The role of the globus pallidus D2 subfamily of dopamine receptors in pallidal immediate early gene expression.
2001
Effect of dopamine D2/D3 receptor antagonist sulpiride on amphetamine-induced changes in striatal extracellular dopamine.
2001 Apr 27
[Initial experiences with amisulpride, an in Germany novel, atypical neuroleptic drug in treatment of adolescents with psychiatric disorders].
2001 Aug
Atypical neuroleptic drugs downregulate dopamine sensitivity in rat cortical and striatal astrocytes.
2001 Aug
Reversal effect of sulpiride on rotational behaviour of rats with unilateral frontal cortex ablation: an alternative explanation for the pharmacological mechanism of its antidepressant effect.
2001 Feb
Facilitated glutamatergic transmission in the striatum of D2 dopamine receptor-deficient mice.
2001 Feb
The role of neurochemical mechanisms of ventromedial hypothalamus in various models of anxiety in rats.
2001 Jan
Effects of hyperprolactinemia on rat prostate growth: evidence of androgeno-dependence.
2001 Jan
[Anti-stress effect of nitric oxide].
2001 Jul-Aug
Pharmacological characterization of the D1- and D2-like dopamine receptors from the brain of the leopard frog, Rana pipiens.
2001 Jun
The role of medial prefrontal cortical dopamine in spontaneous flexibility in the rat.
2001 Jun
The prolactin response to sulpiride in major depression: the role of the D2 receptor in depression.
2001 Jun
Dopamine D(2) receptors mediate amylin's acute satiety effect.
2001 Jun
Dopamine D(2)-like receptors selectively block N-type Ca(2+) channels to reduce GABA release onto rat striatal cholinergic interneurones.
2001 Jun 1
Mutant mice lacking the cholecystokinin2 receptor show a dopamine-dependent hyperactivity and a behavioral sensitization to morphine.
2001 Jun 22
Serotonin, norepinephrine and dopamine involvement in the antidepressant action of hypericum perforatum.
2001 Mar
Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration.
2001 Mar
Intrapallidal D2 dopamine receptors control globus pallidus neuron activity in the rat.
2001 Mar 9
Short-term plasticity at inhibitory synapses in rat striatum and its effects on striatal output.
2001 May
Interaction between D2 dopaminergic and glutamatergic excitatory influences on lower urinary tract function in normal and cerebral-infarcted rats.
2001 May
Development of a high-performance liquid chromatographic method for bioanalytical applications with sulpiride.
2001 Nov 5
Changes in muscle tone are regulated by D1 and D2 dopamine receptors in the ventral striatum and D1 receptors in the substantia nigra.
2001 Oct
Patents

Sample Use Guides

400mg twice daily the doctor may reduce the dose to 200mg twice daily or increase it to a maximum of 1200mg twice daily
Route of Administration: Oral
CHO-K1 D3R cells (DiscoveRx) were seeded at a density of 5000 cells/well in 384-well black, clear-bottom plates. Following 24 h of incubation, the cells were treated with multiple concentrations of the Sulpiride (0-10 μM) in Hanks’ balanced buffer solution containing 2% DMSO. Following a 10 min preincubation, the cells were next treated with an EC95 dose of dopamine (100 nM) and then incubated at 37 C for 90 min. DiscoveRx reagent (2.5) was then added to cells followed by a 60 min incubation at room temperature. Luminescence was measured on a Hamamatsu FDSS μ-cell reader.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:10:00 UTC 2023
Edited
by admin
on Thu Jul 06 02:10:00 UTC 2023
Record UNII
7MNE9M8287
Record Status Validated (UNII)
Record Version
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Name Type Language
SULPIRIDE
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
SURSUMID
Brand Name English
MISULVAN
Brand Name English
sulpiride [INN]
Common Name English
PYRIKAPPL
Brand Name English
COOLSPAN
Brand Name English
SULPIRIDE [JAN]
Common Name English
SYNEDIL
Brand Name English
MIRADOL
Brand Name English
N05AL01
Code English
Sulpiride [WHO-DD]
Common Name English
RD-1403
Code English
NSC-757850
Code English
ABILIT
Brand Name English
SPLOTIN
Brand Name English
SULPIRIDE [EP IMPURITY]
Common Name English
OMPERAN
Brand Name English
N-(1-ETHYL-2-PYRROLIDINYLMETHYL)-2-METHOXY-5-SULFAMIDOBENZAMIDE
Common Name English
MERESA
Brand Name English
SULPIRIDE [MART.]
Common Name English
SERNEVIN
Brand Name English
(±)-SULPIRIDE
Common Name English
N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-SULFAMOYL-O-ANISAMIDE
Common Name English
GUASTIL
Brand Name English
DOGMATYL
Brand Name English
AIGLONYL
Brand Name English
(RS)-(±)-SULPIRIDE
Common Name English
TRILAN
Brand Name English
DOGMATIL
Brand Name English
SULPITIL
Brand Name English
DOBREN
Brand Name English
SULPIRIDE [EP MONOGRAPH]
Common Name English
BENZAMIDE, 5-(AMINOSULFONYL)-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-2-METHOXY-
Systematic Name English
SULPIRIDE [MI]
Common Name English
O-ANISAMIDE, N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-SULFAMOYL-
Common Name English
SULPIRIDE [USAN]
Common Name English
5-(AMINOSULFONYL)-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-2-METHOXYBENZAMIDE
Systematic Name English
NEOGAMA
Brand Name English
SULPOR
Brand Name English
DOLMATIL
Brand Name English
MIRBANIL
Brand Name English
Classification Tree Code System Code
WHO-ATC N05AL01
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
NCI_THESAURUS C66883
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
WHO-VATC QN05AL01
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID1042574
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
FDA UNII
7MNE9M8287
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
NCI_THESAURUS
C87713
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
DRUG BANK
DB00391
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
DAILYMED
7MNE9M8287
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
ChEMBL
CHEMBL26
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
CAS
95204-38-9
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
SUPERSEDED
CAS
15676-16-1
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
PUBCHEM
5355
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
EVMPD
SUB10758MIG
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
NSC
757850
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
RXCUI
10239
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
239-753-7
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
IUPHAR
5501
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
MESH
D013469
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
INN
2359
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
LACTMED
Sulpiride
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
WIKIPEDIA
SULPIRIDE
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
CHEBI
32168
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
MERCK INDEX
M10389
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY Merck Index
SMS_ID
100000091056
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
CAS
23672-06-2
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
SUPERSEDED
DRUG CENTRAL
2537
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
PRIMARY
CAS
51061-74-6
Created by admin on Thu Jul 06 02:10:00 UTC 2023 , Edited by admin on Thu Jul 06 02:10:00 UTC 2023
SUPERSEDED
Related Record Type Details
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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Iron (2.4.9): maximum 10 ppm.
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
Chlorides (2.4.4): maximum 100 ppm.
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY