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Key Documents

C3787

Sigma-Aldrich

Chloramphenicol succinate sodium salt

≥80% (HPLC)

Synonym(s):

Chloramphenicol α-succinate

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About This Item

Linear Formula:
C15H15Cl2N2O8Na
CAS Number:
Molecular Weight:
445.18
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.85

Quality Level

Assay

≥80% (HPLC)

form

solid

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

SMILES string

[Na].O[C@@H]([C@@H](COC(=O)CCC(O)=O)NC(=O)C(Cl)Cl)c1ccc(cc1)N(=O)=O

InChI

1S/C15H16Cl2N2O8.Na.H/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

RJOAHMNSYANTPN-OWVUFADGSA-N

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General description

Chemical structure: phenicole

Application

Chloramphenicol is often used for bacterial selection in molecular biology applications at 10-20 μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.

Biochem/physiol Actions

Chloramphenicol is a synthetic antibiotic, isolated from strains of Streptomyces venezuelae. It inhibits bacterial protein synthesis by blocking the peptidyl transferase step by binding to the 50S ribosomal subunit and preventing attachment of aminoacyl tRNA to the ribosome. It also inhibits mitochondrial and chloroplast protein synthesis and ribosomal formation of (p)ppGpp, de-pressing rRNA transcription.

Mode of Resistance: Use of chloramphenicol acetyltransferase will acetylate the product and inactivate it.

Antimicrobial Spectrum: This is a broad spectrum antibiotic against gram-positive and gram-negative bacteria, and is used mainly for ophthalmic and veterinary purposes.

Caution

Stock solutions should be stored at 2-8°C and are stable at 37°C for 5 days. Aqueous solutions are neutral and stable over a wide pH range, with 50% hydrolysis occurring after 290 days. Use of a borax buffered solution reduces this number to 14%. Solutions should be protected from light as photochemical decomposition results in a yellowing of the solution. Heating aqueous solutions at 115°C for 30 minutes results in a 10% loss of chloramphenicol.

Preparation Note

Stock solutions can be prepared directly in the vial at any recommended concentration. A solution at 50 mg/mL in ethanol yields a clear, very faint, yellow solution. Degradation of chloramphenicol in aqueous solution is catalyzed by general acids and bases. This rate of degradation is independent of the ionic strength and pH.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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G C Allen et al.
Applied and environmental microbiology, 56(4), 1025-1032 (1990-04-01)
Succinate- or oxygen-limited continuous cultures were used to study the influences of different concentrations of dissolved oxygen and ammonia on the growth, respiration, and polypeptide patterns of Bradyrhizobium sp. (Arachis) strain 3G4b20. During succinate-limited growth, molar growth yields on succinate
M W Stinson et al.
Journal of bacteriology, 119(1), 152-161 (1974-07-01)
The ability of succinate to repress the secretion of Pseudomonas lemoignei poly-beta-hydroxybutyrate depolymerase was a function of pH. Repression only occurred when the pH of the medium was 7.0 or less. At a higher pH, lack of sensitivity to succinate
Mode of action of chloramphenicol. III. Action of chloramphenicol on bacterial energy metabolism.
F E HAHN et al.
Journal of bacteriology, 69(2), 215-223 (1955-02-01)
Studies on the mechanism of action of chloramphenicol. I. The conformation of chlioramphenicol in solution.
O JARDETZKY
The Journal of biological chemistry, 238, 2498-2508 (1963-07-01)
Roberta A Gottlieb et al.
Autophagy, 7(4), 434-435 (2010-12-29)
Interventions that reduce infarct size in animal models have largely failed to improve outcome in patients suffering acute myocardial infarction (MI), or 'heart attack'. Our group recently reported a reduction of infarct size by chloramphenicol treatment in a porcine in

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