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C7795 Sigma-Aldrich

Chloramphenicol

γ-irradiated

Synonym: D-(−)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide, D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide, Chloromycetin

  • CAS Number 56-75-7

  • Linear Formula Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2

  • Molecular Weight 323.13

  •  Beilstein/REAXYS Number 2225532

  •  EC Number 200-287-4

  •  MDL number MFCD00078159

  •  PubChem Substance ID 24892989

  •  NACRES NA.31

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics by Application, Antibiotics  A-F, Biochemicals and Reagents,
Quality Level   200
sterility   γ-irradiated
form   powder
pKa    ~5.5
mp   148-150 °C (lit.)
solubility   absolute ethanol: 5-20 mg/mL (as a stock solution)
  methanol: soluble (as a stock solution)
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
  mycobacteria
  mycoplasma
storage temp.   2-8°C
SMILES string   OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O
InChI   1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
InChI key   WIIZWVCIJKGZOK-RKDXNWHRSA-N
Gene Information   human ... CYP1A2(1544)

Description

General description

Chemical structure: phenicole

Application

Chloramphenicol is a synthetic antibiotic, isolated from strains of Streptomyces venezuelae. It 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

Mode of Action: Chloramphenicol 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 concentration in the recommended range. 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. Light sensitive.

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
AB6825000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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