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Sulpiride

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Sulpiride Basic information

Product Name:
Sulpiride
Synonyms:
  • R.D. 1403
  • rac Sulpiride
  • (RS)-(+/-)-SULPIRIDE
  • (RS)-(+/-)-5-AMINOSULFONYL-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-2-METHOXYBENZAMIDE
  • (+/-)-SULPIRIDE
  • SULPIRIDE
  • Abilit
  • Aiglonyl
CAS:
15676-16-1
MF:
C15H23N3O4S
MW:
341.43
EINECS:
239-753-7
Product Categories:
  • DOGMATYL
  • Aromatics
  • Dopamine receptor
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulpiride
Mol File:
15676-16-1.mol
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Sulpiride Chemical Properties

Melting point:
178-180°
alpha 
D25 -66.8° (c = 0.5 in DMF)
Density 
1.2375 (rough estimate)
refractive index 
1.6320 (estimate)
storage temp. 
2-8°C
solubility 
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 8.0 mg/mL
form 
powder
pka
pKa1 9.00, pKa2 10.19(at 25℃)
color 
yellow
Water Solubility 
<0.21g/L(25 ºC)
λmax
232nm(EtOH)(lit.)
Merck 
14,8989
InChIKey
BGRJTUBHPOOWDU-UHFFFAOYSA-N
LogP
0.57
CAS DataBase Reference
15676-16-1(CAS DataBase Reference)
NIST Chemistry Reference
Sulpiride(15676-16-1)
EPA Substance Registry System
Sulpiride (15676-16-1)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
BZ3400000
Toxicity
LD50 in mice (mg/kg): 170 i.p.; 2250 orally (Dostert)

MSDS

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Sulpiride Usage And Synthesis

Chemical Properties

Sulpiride is White Solid

Originator

Dogmatil,Delagrange,France,1969

Uses

Sulpiride is an antipsychotic drug used in the treatment of Schozophrenia and depression.

Uses

dopamine receptor antagonist, antipsychotic

Uses

Sulpiride possesses moderate neuroleptic activity along with some stimulating and antidepressant effects. It has antiemetic, moderately cataleptogenic, and antiserotonin action. It facilitates increased blood flow in the stomach. It speeds up the restorative processes in tissues. It is used for schizophrenia, depression, migraines, disturbance of behavioral functions, and stomach and duodenal ulcers.

Definition

Sulpiride is 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.

Manufacturing Process

1-Ethyl-2-aminomethylpyrrolidine is reacted with 2-methoxy-5- sulfamoylbenzoic acid to give sulpiride.

brand name

Dogmatyl (Laboratoires Delagrange, France).

Therapeutic Function

Tranquilizer, Digestive aid

Biological Activity

Standard D 2 -like dopamine receptor antagonist.

Biochem/physiol Actions

(±)-Sulpiride is a D2 dopamine antagonist and an effective treatment for schizophrenia when used in combination with clozapine, a relatively weak D2-dopaminergic antagonist. It is an antipsychotic agent and also exhibits neuroleptic properties but poorly penetrates the central nervous system.45,46

Clinical Use

Antipsychotic:
Acute and chronic schizophrenia

Synthesis

Sulpiride, N-[(1-ethyl-2-pirrolidinylmethyl]-5-sulfamoyl-O-anizamide (6.7.2), is synthesized from 5-aminosulfosalycilic acid. Methylating this with dimethylsulfate gives 2-methoxy-5-aminosulfonylbenzoic acid (6.7.1), which is transformed into an amide using 2-aminomethyl-1-ethylpyrrolidine as amine components and carbonyl-1,1′-bisimidazole as a condensing agent [70–74].

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedativeeffects with opioids; increased risk of ventricular arrhythmias with methadone.
Anti-arrhythmics increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval, e.g. procainamide, disopyramide and amiodarone - avoid with amiodarone.
Antibacterials: increased risk of ventricular arrhythmias with moxifloxacin and parenteral erythromycin - avoid with moxifloxacin.
Antidepressants: possibly increased risk of ventricular arrhythmias and antimuscarinic side effects with tricyclics - avoid.
Antiepileptics: antagonism (convulsive threshold lowered).
Antimalarials: avoid with artemether/lumefantrine.
Antipsychotics: increased risk of ventricular arrhythmias with droperidol, haloperidol and pimozide - avoid; possible increased risk of ventricular arrhythmias with risperidone.
Antivirals: concentration possibly increased by ritonavir.
Anxiolytics and hypnotics: increased sedative effects.
Atomoxetine: increased risk of ventricular arrhythmias.
Beta-blockers: enhanced hypotensive effect; increased risk of ventricular arrhythmias with sotalol.
Cytotoxics: increased risk of ventricular arrhythmias with vandetanib - avoid; increased risk of ventricular arrhythmias with arsenic trioxide.
Diuretics: enhanced hypotensive effect.
Lithium: increased risk of extrapyramidal side effects and possibly neurotoxicity.
Pentamidine: increased risk of ventricular arrhythmias.

Metabolism

Sulpiride undergoes little metabolism.
95% of a dose is excreted in the urine and faeces, mainly as unchanged drug.

Sulpiride Preparation Products And Raw materials

Raw materials

Preparation Products

SulpirideSupplier

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