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Amisulpride

Amisulpride structure

CAS No:
71675-85-9
Formula:
C17H27N3O4S
Chemical Name:
Amisulpride
Synonyms:
Benzamide,4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxy-;4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide;Amisulpride;(±)-Amisulpride;DAN 2163;Aminosultopride;Solian;Socian;Deniban;4-Amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide;Amipride;Paxiprid;Joykem;Barhemsys;97229-16-8
Categories:
Active Pharmaceutical Ingredients > Nervous System Drugs

Description

Amisulpride is a dopamine D2/D3 receptor antagonist with Kis of 2.8 and 3.2 nM for human dopamine D2 and D3, respectively.

Solid

Amisulpride is 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. It has a role as a second generation antipsychotic, a xenobiotic and an environmental contaminant. It is a member of pyrrolidines, an aromatic amine, a sulfone, a member of benzamides and an aromatic amide.|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.|A benzamide derivative that is used as an antipsychotic agent for the treatment of schizophrenia. It is also used as an antidepressive agent.

Amisulpride Basic Attributes

Molecular Weight：

369.48

Exact Mass：

369.48

EC Number：

275-831-7

NSC Number：

760085

DSSTox ID：

DTXSID5042613

ATC Code：

N05AL05|N - Nervous system

HScode：

2933990090

Characteristics

PSA：

110

XLogP3：

1.5

Appearance：

white solid

Density：

1.2±0.1 g/cm3

Melting Point：

126-127 °C

Boiling Point：

558.9°C at 760 mmHg

Flash Point：

291.8±30.1 °C

Refractive Index：

1.546

Water Solubility：

DMSO: ≥5 mg/mL

Storage Conditions：

2-8°C

Toxicity：

LD50 in male mice (mg/kg): 56-60 i.v.; 175-180 i.p.; 224-250 s.c.; 1024-1054 orally (Thominet)

Dissociation Constants：

9.37

Collision Cross Section：

193.1 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

22-24/25

RTECS Number：

CV2308701

Marks：

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (91.38%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 60 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Overdoses of amisulpride have been linked with torsades de pointes.

Protein Binding：

Low (17%)

Drug Information

Drug Indication：

Investigated for use/treatment in schizophrenia and schizoaffective disorders, mania in bipolar disorder, and depression.

Drug Transformations：

Amisulpride has known transformation products that include Amisulpride N-oxide.

MeSH：

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)|A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)|Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

Absorption：

Bioavailability is 48% following oral administration.

Biological Half-Life：

Approximately 12 hours

Mechanism of Action：

Amisulpride binds selectively to dopamine D(2) and D(3) receptors in the limbic system. Low doses of amisulpride preferentially block presynaptic D(2)/D(3)-dopamine autoreceptors, thereby enhancing dopaminergic transmission, whereas higher doses block postsynaptic receptors, thus inhibiting dopaminergic hyperactivity. It may also have 5-ht7 antagonistic effect, useful in depression treatment.

MeSH Entry Terms：

4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Amisulpride Use and Manufacturing

Methods of Manufacturing

To a stirring mixture of 4-amino-2-methoxy-5 -ethyl sulphonyl benzoic acid (IV) and acetone (5.0 L) at 0-5°C, triethyl amine (0.405 Kg) was added and stirred followed by addition of ethyl chloroformate (0.368 Kg). N-ethyl-2-amino methyl pyrrolidine (0.627 Kg) was added to the reaction mass at 5-10°C. Temperature of reaction mass was raised to 25-30°C and stirred for 120 min. To the same reaction mass triethyl amine (0.405 Kg) and ethyl chloroformate (0.368 Kg) was added with maintaining the temperature. Reaction mass was stirred for 120 min. After completion of reaction, water (4.0 L) was added. Reaction mass was filtered and washed with water (2.0 L). Filtrate was collected and water was added (9.0 L). pH of the reaction mass was adjusted to 10.8-1 1.2 by using 20percent NaOH solution. Reaction mass was stirred for 240-300 min, filtered and washed with water. Solid was dried under vacuumYield : 70percentPurity: 98percent

Uses

Amisulpride is a neuroleptic agent, an analogue of Sulpiride (S689145). Amisulpride is used as an antipsychotic. Amisulpride is a dopamine receptor antagonist. Specific D2/D3 receptor antagonist, treats the positive and negative symptoms of acute and chronic schizophrenia.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals|Pharmaceuticals -> Neuroleptics

Computed Properties

Molecular Weight:369.5
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:369.17222752
Monoisotopic Mass:369.17222752
Topological Polar Surface Area:110
Heavy Atom Count:25
Complexity:549
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Amisulpride is an aniline substitute neuroleptic drug that selectively binds to the D2 and D3 dopamine receptors in the limbic system. It does not bind to serotonergic receptors or other histamine, cholinergic, and adrenergic receptors. High doses of amisulpride mainly block dopaminergic neurons in the central part of the limbic system, while low doses of amisulpride mainly block presynaptic D2/D3 dopamine receptors. Compared with haloperidol, amisulpride can significantly improve patients' secondary negative symptoms.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Amisulpride Tablets
Ingredients	Amisulpride
Indication	Contraindications: 1. Drugs that may cause torsades de pointes: - Class Ia antiarrhythmic drugs, such as quinidine, hydroquinidine, disopyramide. - Class III antiarrhythmic drugs, such as amiodarone, sotalol, dofetilide, ibutilide. - Certain sedatives, such as thioridazine, chlorpromazine, levomepromazine, trifluoperazine, cyanomemazine, sulpiride, tiapride, sultopride, pimozide, haloperidol, droperidol. - Other drugs, such as bepridil, cisapride, methadone, diphenylmanil, intravenous erythromycin, mizolastine, intravenous vincamine, halofantrine, pentamidine, sparfloxacin, moxifloxacin. 2. Levodopa: There is an antagonistic effect between levodopa and sedatives. 3. Except for the treatment of patients with Parkinson's disease, this product is prohibited from being used in combination with dopamine agonists other than levodopa (amantadine, anhydrous morphine, bromocriptine, cabergoline, entacapone, lisulide, pergolide, piribedil, pramipexole, quinagolide, ropinirole). Dopamine agonists and sedatives have mutual antagonism. When extrapyramidal symptoms induced by sedatives occur, do not use dopamine agonists for treatment, and anticholinergic drugs should be used. Unrecommended combined use: 1. Amisulpride may enhance the effects of alcohol on the central nervous system. 2. Drugs that increase the risk of torsades de pointes or may prolong the QT interval: a) Drugs that cause bradycardia, such as beta-blockers, calcium channel blockers that cause bradycardia, such as diltiazem and verapamil, clonidine, guanfacine; digitalis. b) Drugs that cause hypokalemia: hypokalemic diuretics, stimulant laxatives, intravenous amphotericin B, glucocorticoids, teicosatide. Hypokalemia should be corrected. c) Psychotropic sedatives, such as pimozide, haloperidol: imipramine antidepressants: lithium. Co-administration that needs to be carefully considered: 1. CNS depressants, including opioid anesthetics, analgesics, H1 antihistamine sedatives, barbiturates, benzodiazepines and other anxiolytics, clonidine and derivatives. 2. Antihypertensive drugs and other blood pressure lowering drugs.
Specifications	0.2 g

Amisulpride Tablets
Ingredients	Amisulpride
Indication	Combination medication is not recommended: . Amisulpride can enhance the central effects of alcohol. . Drugs that increase the risk of torsade de pointes or can prolong the QT time. Drugs that cause bradycardia: such as beta-blockers, calcium channel blockers that cause bradycardia: such as diltiazem and verapamil, clonidine, guanfacine; digitalis. Drugs that cause hypokalemia: potassium-lowering diuretics, stimulant laxatives, intravenous amikacin B, glucocorticoids, tetracosactide. Hypokalemia should be corrected. Psychotropic sedatives: such as pimozide, haloperidol, imipramine antidepressants, lithium. Combination medications that need to be carefully considered. . CNS depressants: including opioid anesthetics, analgesics, H1 antihistamine sedatives, barbiturates, benzodiazepines and other anxiolytics, clonidine and derivatives
Specifications	50mg
Manufacturer	Qilu Pharmaceutical Co., Ltd.

Amisulpride Tablets
Specifications	0.2g

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Registered Holders

COSMA S.P.A.

Brazil
Active
Hetero Pharma (Beijing) Co., Limited

China
Active
Shandong Anhong Pharmaceutical Co., Ltd.

China
Active

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