15676-16-1 Usage
Description
Sulpiride is a member of the benzamides class, derived from the formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine. It is a white solid with various applications in the medical field.
Used in Pharmaceutical Industry:
Sulpiride is used as an antipsychotic drug for the treatment of schizophrenia and depression. It acts as a dopamine receptor antagonist, providing neuroleptic activity along with stimulating and antidepressant effects.
Used in Gastrointestinal Applications:
Sulpiride is used as an antiemetic to alleviate nausea and vomiting. It also facilitates increased blood flow in the stomach, aiding in the restorative processes of tissues and is used for the treatment of stomach and duodenal ulcers.
Used in Neurological Applications:
Sulpiride is used as a moderately cataleptogenic agent, which helps in the treatment of neurological disorders. It also possesses antiserotonin action, which can be beneficial in managing certain conditions related to serotonin imbalances.
Used in Behavioral Applications:
Sulpiride is used to address disturbances in behavioral functions, providing relief from conditions that affect an individual's behavior and mental state.
Used in Migraines Treatment:
Sulpiride is used as a treatment option for migraines, helping to alleviate the symptoms and reduce the frequency of these headaches.
Brand Name:
Sulpiride is available under the brand name Dogmatyl, manufactured by Laboratoires Delagrange in France.
Originator
Dogmatil,Delagrange,France,1969
Manufacturing Process
1-Ethyl-2-aminomethylpyrrolidine is reacted with 2-methoxy-5-
sulfamoylbenzoic acid to give sulpiride.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 15676-16-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,6,7 and 6 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 15676-16:
(7*1)+(6*5)+(5*6)+(4*7)+(3*6)+(2*1)+(1*6)=121
121 % 10 = 1
So 15676-16-1 is a valid CAS Registry Number.
InChI:InChI=1/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)/p+1/t11-/m1/s1
15676-16-1Relevant articles and documents
Photoactivatable Dopamine and Sulpiride to Explore the Function of Dopaminergic Neurons and Circuits
Asad, Naeem,Condon, Alec F.,Dore, Timothy M.,Gore, Sangram,Hampton, Shahienaz E.,Mclain, Duncan E.,Vijay, Sauparnika,Williams, John T.
, p. 939 - 951 (2020)
Kinetic analysis of dopamine receptor activation and inactivation and the study of dopamine-dependent signaling requires precise simulation of the presynaptic release of the neurotransmitter dopamine and tight temporal control over the release of dopamine receptor antagonists. The 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting group was conjugated to dopamine and the dopamine receptor antagonist sulpiride to generate "caged" versions of these neuromodulators (CyHQ-O-DA and CyHQ-sulpiride, respectively) that could release their payloads with 365 or 405 nm light or through 2-photon excitation (2PE) at 740 nm. These compounds are stable under physiological conditions in the dark, yet photolyze rapidly and cleanly to yield dopamine or sulpiride and the caging remnant CyHQ-OH. CyHQ-O-DA mediated the light activation of dopamine-1 (D1) receptors on the breast cancer cell line MDA-MB-231 in culture. In mouse brain slice from the substantia nigra pars compacta, localized flash photolysis of CyHQ-O-DA accurately mimicked the natural presynaptic release of dopamine and activation of dopamine-2 (D2) receptors, causing a robust, concentration-dependent, and repeatable G protein-coupled inwardly rectifying potassium channel-mediated outward current in whole-cell voltage clamp recordings that was amplified by cocaine and blocked by sulpiride. Photolysis of CyHQ-sulpiride rapidly blocked synaptic activity, enabling measurement of the unbinding rates of dopamine and quinpirole, a D2 receptor agonist. These tools will enable more detailed study of dopamine receptors, their interactions with other GPCRs, and the physiology of dopamine signaling in the brain.
A postoperative or its optical isomers of synthetic and post-processing method
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Paragraph 0024; 0025, (2018/09/11)
The invention relates to a synthesis and post-processing method of sulpiride or an optical isomer thereof, and the synthesis and post-processing method include the following steps: under inert gas protection, heating 2-methoxy-5-aminosulfonyl methyl benzoate or 2-methoxy-5-aminosulfonyl ethyl benzoate and 1-ethyl-2-aminomethyl pyrrolidine or an optical isomer thereof at 80-120 DEG C for a plurality of hours, and after the reaction is completed, adding ethanol for processing, cooling, filtering, washing and drying.
A method for preparing shu Bili (by machine translation)
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Paragraph 0013; 0014; 0015, (2017/02/17)
The invention discloses a method for preparing sulpiride. The method comprises the following steps: firstly, carrying out condensation reaction on 2-methoxy-5-aminosulfanoyl methyl benzoate and N-ethyl-2-aminomethyl tetrahydropyrrole to generate a crude sulpiride product; and refining the crude sulpiride product to obtain a refined sulpiride product. The sulpiride prepared by the method has the advantages of good quality, high purity, simple preparation method, low energy consumption and low cost.