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Levosulpiride

Levosulpiride structure

CAS No:
23672-07-3
Formula:
C15H23N3O4S
Chemical Name:
Levosulpiride
Synonyms:
Benzamide,5-(aminosulfonyl)-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-methoxy-;o-Anisamide,N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-sulfamoyl-,(-)-;Benzamide,5-(aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-,(S)-;5-(Aminosulfonyl)-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-methoxybenzamide;l-Sulpiride;(-)-Sulpiride;L-Sulpiride;S-(-)-Sulpiride;S-Sulpiride;Levosulpiride;Levobren;Levopraid;sulpid;levopride;Lesuride
Categories:
Biochemical Engineering > Inhibitors

Description

Levosulpiride (RV-12309) is the (S)-enantiomer of sulpiride, which is a D2 receptor a antagonist, an atypical antipsychotic drug of the benzamide class.

(S)-(-)-sulpiride is an optically active form of sulpiride having (S)-configuration. The active enantiomer of the racemic drug sulpiride. Selective D2-like dopamine antagonist (Ki values are ~ 0.015. ~ 0.013, 1, ~ 45 and ~ 77 muM at D2, D3, D4, D1 and D5 receptors respectively). It has a role as a dopaminergic antagonist, an antidepressant, an antiemetic and an antipsychotic agent. It is an enantiomer of a (R)-(+)-sulpiride.

Levosulpiride Basic Attributes

Molecular Weight：

341.43

Exact Mass：

341.43

EC Number：

233-599-4

UNII：

JTG7R315LK

DSSTox ID：

DTXSID0042583

ATC Code：

N - Nervous system

HScode：

29350090

Characteristics

PSA：

110

XLogP3：

0.6

Appearance：

white crystalline powder

Density：

1.2±0.1 g/cm3

Melting Point：

185-187 °C

Refractive Index：

1.552

Storage Conditions：

2-8°C

Toxicity：

LD50 oral in rabbit: > 1500mg/kg

Safety Information

Transport codes：

3077

wgk germany：

RTECS Number：

BZ3400100

Drug Information

MeSH Entry Terms：

levopraid

Levosulpiride Use and Manufacturing

Methods of Manufacturing

Method 1: The preparation is the same as sulpiride, except that 2-aminomethyl-1-ethylpyrrolidine is chemically resolved before reacting with methyl 2-methoxy-5-aminosulfonylbenzoate, React after getting S type. At room temperature, the racemic 2-aminomethyl-1-ethylpyrrolidine was added dropwise to the aqueous solution of D-(-)-tartaric acid and stirred. Then add absolute ethanol and place in the refrigerator overnight. The solid was collected by filtration, refluxed with methanol, hot filtered, and dried to obtain tartrate in a yield of 36.8%. The salt and aqueous sodium hydroxide solution were stirred at room temperature and extracted with chloroform. The extract was dried and concentrated, distilled under reduced pressure, and the 65°C/2.0kPa fraction was collected to obtain (S)-(-)-2aminomethyl-1-ethylpyrrolidine, with a yield of 43.5%. The obtained S-type pyrrolidine and methyl 2-methoxy-5-aminosulfonylbenzoate were stirred in ethylene glycol at 120°C. After cooling to 5°C and filtering, the obtained crude product was recrystallized with 95% ethanol to obtain sulpiride, the yield was 72.6%, the melting point was 184-186°C, [α]D23-66.4° (C=0.5, dimethylformamide). Method 2: Using L-proline as the raw material, levosupride is obtained through five steps of acylation, reduction, chlorination, amination and condensation. L-proline is dissolved in water, and acetic anhydride is added dropwise. Stir at 90°C, cool, filter with suction, and wash with a little ice water. The filtrate was concentrated to 1/2 volume, and isopropyl alcohol was added. The crystals were collected by filtration and dried to obtain the acylated product LN-acetylproline in 90% yield. Dissolve it in tetrahydrofuran, slowly drop in a solution of lithium aluminum hydride in tetrahydrofuran, and reflux. Under ice bath cooling, the mixed solution of tetrahydrofuran and water was added dropwise, and then 20% sodium hydroxide solution was added dropwise. Filter, dry the filtrate and filter again. The solvent was distilled off, and the 76-78°C/2.0kPa fraction was collected to obtain compound (I) in a yield of 79.8%. The compound (I) was dissolved in dichloromethane, and sulfoxide chloride was slowly added dropwise under ice-cooling, stirred at room temperature and then refluxed. Concentrate to the point, add absolute ethanol-ammonia solution and stir at 20℃. The solvent was distilled off, water was added, and 50% sodium hydroxide was adjusted to a Ph value of 10. Diethyl ether was extracted, dried, filtered, the solvent was distilled off, and the fraction of 70-74°C/1.6kPa was collected to obtain compound (II) in a yield of 65%. Compound (II) and Compound (III) are dissolved in ethylene glycol, stirred at 80-85°C, and the methanol produced is distilled off. Cool, filter, and recrystallize ethanol to obtain sulpiride, yield. 75%, melting point 186-187°C, [α]D20-68.79° (C=1%, dimethylformamide).

Uses

Dopamine D2 and D3-receptor antagonist. Antipsychotic; antidepressant; antiemetic.

Computed Properties

Molecular Weight:341.4
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:341.14092740
Monoisotopic Mass:341.14092740
Topological Polar Surface Area:110
Heavy Atom Count:23
Complexity:505
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Sodium hydroxide

Ethanol

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