A prodrug form of chloramphenicol
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Chloramphenicol Succinate

Item No. 25453

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
butanedioic acid, mono[(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester
CAS Number
3544-94-3
Molecular Formula
C15H16Cl2N2O8
Formula Weight
423.2
Purity
≥99%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C(CCC(O)=O)OC[C@@H](NC(C(Cl)Cl)=O)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1
InChi Code
InChI=1S/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
InChi Key
LIRCDOVJWUGTMW-ZWNOBZJWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Chloramphenicol succinate is a water-soluble prodrug form of the antibiotic chloramphenicol.1 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.2 Chloramphenicol succinate reduces human leukocyte migration in vitro.3 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.4 Chloramphenicol succinate (20 mg/kg) reduces infarct size in a porcine model of myocardial ischemia-reperfusion injury.5 Formulations containing chloramphenicol succinate have been used in the treatment of severe bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ceriotti, G., Defranceschi, A., De Carneri, I., et al. Chloramphenicol succinate, a water-soluble derivative of chloramphenicol. Farmaco Sci. 9(1), 21-38 (1954).

    2. Ambekar, C.S., Lee, J.S., Cheung, B.M., et al. Chloramphenicol succinate, a competitive substrate and inhibitor of succinate dehydrogenase: Possible reason for its toxicity. Toxicol. In Vitro 18(4), 441-447 (2004).

    3. Forsgren, A., and Schmeling, D. Effect of antibiotics of chemotaxis of human leukocytes. Antimicrob. Agents Chemother. 11(4), 590-584 (1977).

    4. Prat, V., Konickova, L., Ritzerfeld, W., et al. Effect of chloramphenicol against different E. coli strains in vitro and in experimental pyelonephritis. Arzneimittelforschung 18(9), 1123-1127 (1968).

    5. Sala-Mercado, J.A., Wider, J., Undyala, V.V., et al. Profound cardioprotection with chloramphenicol succinate in the swine model of myocardial ischemia-reperfusion injury. Circulation 122(11 Suppl), S179-S184 (2010).