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 hemisuccinate, also known as chloramphenicol succinate, is a water-soluble prodrug form of the antibiotic chloramphenicol. It is designed to improve the solubility and bioavailability of chloramphenicol, allowing for more effective delivery and absorption in the body. Chloramphenicol hemisuccinate is a substrate for succinate dehydrogenase (SDH) and is oxidized by human liver and rat liver and kidney mitochondria to release the active antibiotic chloramphenicol.

Uses

Used in Surface Antibiotic Treatment in Surgery:
Chloramphenicol hemisuccinate is used as a surface antibiotic agent for surgical procedures. It provides a localized and targeted approach to infection prevention and treatment, reducing the risk of systemic side effects and promoting faster recovery.
Used in the Treatment of Severe Bacterial Infections:
Chloramphenicol hemisuccinate is used as an antibiotic for the treatment of severe bacterial infections. It is particularly effective against a wide range of gram-positive and gram-negative bacteria, including those resistant to other antibiotics.
Used in Animal Models for Infection Treatment:
Chloramphenicol hemisuccinate has been shown to reduce E. coli growth in rabbit and rat models of pyelonephritis when administered at doses of 150 and 200 mg/kg, respectively. This indicates its potential use in veterinary medicine for the treatment of bacterial infections in animals.
Used in Myocardial Ischemia-Reperfusion Injury Treatment:
Chloramphenicol hemisuccinate (20 mg/kg) has been shown to reduce infarct size in a porcine model of myocardial ischemia-reperfusion injury. This suggests its potential use in the treatment of heart conditions where inflammation and infection play a role in the pathology.

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

• 132752-58-0 (1RS,2SR)-3-(3-carboxy-propionyloxy)-1-chloro-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propane 
• 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 

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).