Chloramphenicol succinate

Base Information

• Chemical Name: Chloramphenicol succinate
• CAS No.: 3544-94-3
• Deprecated CAS: 53906-65-3
• Molecular Formula: C15H16 Cl2 N2 O8
• Molecular Weight: 423.207
• European Community (EC) Number: 222-590-0
• NSC Number: 756676
• UNII: ZCX619U9A1
• DSSTox Substance ID: DTXSID8048155
• Wikidata: Q27096784
• Metabolomics Workbench ID: 69973
• ChEMBL ID: CHEMBL1201281
• Mol file: 3544-94-3.mol

Synonyms:chloramphenicol hemisuccinate;chloramphenicol monosuccinate;chloramphenicol sodium succinate;chloramphenicol succinate;chloramphenicol succinate sodium;levomycetin succinate

Chemical Property of Chloramphenicol succinate

Chemical Property:

• Vapor Pressure: 1.56E-21mmHg at 25°C
• Melting Point: 127 °C
• Refractive Index: 1.7350 (estimate)
• Boiling Point: 716.3°Cat760mmHg
• PKA: 4.36±0.17(Predicted)
• Flash Point: 387°C
• PSA: 162.24000
• Density: 1.536g/cm³
• LogP: 2.68820
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 422.0283709
• Heavy Atom Count: 27
• Complexity: 546

Purity/Quality:

99.9% ^*data from raw suppliers

ChloramphenicolSuccinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(COC(=O)CCC(=O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@H]([C@@H](COC(=O)CCC(=O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• 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.

Technology Process of Chloramphenicol succinate

There total 6 articles about Chloramphenicol succinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

succinic acid anhydride (108-30-5) + chloramphenicol (56-75-7,85666-84-8) → threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-succinate (3544-94-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; Reagent/catalyst;

Reference yield:

chloramphenicol succinate sodium → threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-succinate (3544-94-3)

Guidance literature:

With hydrogenchloride; water; In chloroform;

DOI:10.1021/ac801301p

Reference yield:

(1RS,2RS)-3-(3-carboxy-propionyloxy)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol (3544-94-3,13050-84-5,119008-85-4) + strychnidin-10-one (57-24-9) → threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-succinate (3544-94-3)

Guidance literature:

upstream raw materials:

(1RS,2RS)-3-(3-carboxy-propionyloxy)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol

strychnidin-10-one

succinic acid anhydride

chloramphenicol

Downstream raw materials:

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

(1S,2S)-3-(3-carboxy-propionyloxy)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol

chloroamphenicol-1-monosuccinate

Refernces

• 1、 Wang, Jiaqing,Shy, Adrianna,Wu, Difei,Cooper, Deani L.,Xu, Jiashu,He, Hongjian,Zhan, Wenjun,Sun, Shenghuan,Lovett, Susan T.,Xu, Bing. "Structure-Activity Relationship of Peptide-Conjugated Chloramphenicol for Inhibiting Escherichia coli". . p. 10245 - 10257. Retrieved 2019.
• 2、 Yuan, Jing,Oliver, Richard,Aguilar, Marie-Isabel,Wu, Yinqiu. "Surface plasmon resonance assay for chloramphenicol". experimental part. p. 8329 - 8333. Retrieved 2009/04/07.