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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

BZ3400000

HS Code 

2933.99.6100

Toxicity

LD50 in mice (mg/kg): 170 i.p.; 2250 orally (Dostert)

MSDS

• Language:English Provider:5-(Aminosufonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide
• Language:English Provider:SigmaAldrich

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¨C74].

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.

storage

Room temperature

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