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C6455 Sigma-Aldrich

Chloramphenicol

powder, Sigma Reference Standard

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 24892868

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Properties

grade   Sigma Reference Standard
form   powder
packaging   vial of 200 mg
color   white
mp   148-150 °C (lit.)
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   viruses
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

Used as a seletion agent for transformed cells containing chloramphenicol resistance 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.

Mode of Action: Inhibits cell wall protein synthesis at the level of peptidyl transferase activity associated with the 23S rRNA of the 50S ribosomal subunit.
Antimicrobial spectrum: Gram-positive cocci.
Mode of Resistance: Cephalosporinase production.

Packaging

Supplied in amber screw-cap vials

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
AB6825000
Protocols & Articles
Peer-Reviewed Papers
15

References

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