3544-94-3

Basic information

• Product Name: Chloramphenicol hemisuccinate
• Synonyms: [2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] hydrogen [R-(R*,R*)]-succinate;Chloramphenicol succinate;Acetamide, 2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-, α-(hydrogen succinate), D-(-)-threo- (8CI);Butanedioic acid, mono[(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester;Butanedioic acid, mono[2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester, [R-(R*,R*)]-;Chloramphenicol 3-monosuccinate;Chloramphenicol acid succinate;Chloramphenicol hemisuccinate
• CAS NO: 3544-94-3
• Molecular Formula: C₁₅H₁₆Cl₂N₂O₈
• Molecular Weight: 423.2
• EINECS: 222-590-0
• Mol File: 3544-94-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 127 °C
• Boiling Point: 716.3°Cat760mmHg
• Flash Point: 387°C
• Appearance: /
• Density: 1.6769 (rough estimate)
• Vapor Pressure: 1.56E-21mmHg at 25°C
• Refractive Index: 1.7350 (estimate)
• PKA: 4.36±0.17(Predicted)
• CAS DataBase Reference: Chloramphenicol hemisuccinate(CAS DataBase Reference)
• NIST Chemistry Reference: Chloramphenicol hemisuccinate(3544-94-3)
• EPA Substance Registry System: Chloramphenicol hemisuccinate(3544-94-3)

Safety Data

• Hazardous Substances Data: 3544-94-3(Hazardous Substances Data)

Usage

Description

Chloramphenicol succinate is a water-soluble prodrug form of the antibiotic chloramphenicol. It is a substrate for succinate dehydrogenase (SDH) and is oxidized by human liver and rat liver and kidney mitochondria to release chloramphenicol in vitro. Chloramphenicol succinate reduces human leukocyte migration in vitro. In vivo, chloramphenicol succinate reduces E. coli growth in rabbit and rat models of pyelonephritis when administered at doses of 150 and 200 mg/kg, respectively. Chloramphenicol succinate (20 mg/kg) reduces infarct size in a porcine model of myocardial ischemia-reperfusion injury. Formulations containing chloramphenicol succinate have been used in the treatment of severe bacterial infections.

Uses

Chloramphenicol succinate is prepared by acylation of chloramphenicol with succinic anhydride to provide a water soluble pro-drug. Chloramphenicol succinate represents an alternative pro-drug strategy for chloramphenicol that has found a niche in surface antibiotic treatment in surgery. Chloramphenicol succinate is significantly less active than chloramphenicol but acts as a prodrug, forming chloramphenicol in the presence of succinate dehydrogenase.

InChI:InChI=1/C15H16Cl2N2O8/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21)/t10-,13-/m1/s1

Upstream product

• 3544-94-3 (1RS,2RS)-3-(3-carboxy-propionyloxy)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol 
• 57-24-9 strychnidin-10-one 
• 108-30-5 succinic acid anhydride 
• 56-75-7 chloramphenicol 
• 75725-02-9 chloroamphenicol-1-monosuccinate 

Downstream Products

• 3544-94-3 (1S,2S)-3-(3-carboxy-propionyloxy)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol 
• 75725-02-9 chloroamphenicol-1-monosuccinate 
• 132752-58-0 (1RS,2SR)-3-(3-carboxy-propionyloxy)-1-chloro-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propane 

Relevant articles and documents

High-pressure liquid chromatographic assay for chloramphenicol, chloramphenicol-3-monosuccinate, and chloramphenicol-1-monosuccinate

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Chloramphenicol sodium succinate synthesis method

The invention discloses a chloramphenicol sodium succinate synthesis method, which comprises: preparing chloramphenicol hemisuccinate by using chloramphenicol and succinic anhydride as raw materials,preparing chloramphenicol succinamide from the chloramphenicol hemisuccinate and ethanolamine, carrying out acidification treatment on the chloramphenicol succinamide to obtain high-purity chloramphenicol hemisuccinate monoester, and preparing chloramphenicol sodium succinate by using the chloramphenicol hemisuccinate monoester and sodium isooctanoate as raw materials. According to the present invention, the chloramphenicol sodium succinate is directly prepared by using the simple and easily-available preparation process, and has characteristics of high purity and high yield; the obtained product can be directly used so as to simplify the use process and achieve the good use effect; and the synthesis method provides the reliable method for the industrial preparation of chloramphenicol sodium succinate, has advantages of easily available raw materials, mild reaction conditions, short time, solvent recovery, simple and easy-performing operation, simple equipment and the like, and has theproduct yield of over 80%, wherein the content determined by liquid chromatography and UV-visible spectrophotometer is up to more than 99%.

Synthesis of Ester Derivatives of Chloramphenicol by Lipase-Catalyzed Transesterification in Organic Solvents

Regioselective esterification of chloramphenicol (1) and its synthetic analogue thiamphenicol (2) has been achieved by the action of lipase in acetone and several methyl carboxylates.Aliphatic and aromatic esters of different sizes and natures have been introduced selectively on the primary hydroxyl group of these molecules by modification of the reaction conditions (e.g., temperature, solvent, and lipase source).