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23275

Chloramphenicol

≥99.0% (HPLC)

Synonym(s):

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

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About This Item

Linear Formula:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
CAS Number:
56-75-7
Molecular Weight:
323.13
EC Number:
200-287-4
UNSPSC Code:
51101500
MDL number:
MFCD00078159
Beilstein/REAXYS Number:
2225532
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assay

≥99.0% (HPLC)

optical activity

[α]20/D +19.5±1°, c = 5% in ethanol

mp

149-151 °C, 149-153 °C (lit.)

antibiotic activity spectrum

viruses

mode of action

protein synthesis | interferes

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

General description

Chemical structure: phenicole

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.

Other Notes

Inhibits protein biosynthesis by binding to the large subunit of the bacterial ribosome and by blocking the peptidyl transfer; chloramphenicol-resistance is a useful genetic marker for the selection of eukaryotic cells; Resistance is usually mediated by a chloramphenicol-acetyl-transferase, but there are exceptions; Review.

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pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

涉药品监管产品

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W. Shaw
Methods in Enzymology, 53, 737-737 (1975)
L.C. Vining et al.
Drugs Pharm. Sci., 22, 387-387 (1984)
D F Gaffney et al.
Journal of general microbiology, 125(1), 113-121 (1981-07-01)
Chloramphenicol resistance-specifying plasmids from incompatibility groups P-1 and C did not encode chloramphenicol acetyltransferase (CAT). Expression of resistance was inducible by subinhibitory concentrations of the drug. The mechanism of resistance was thought to be a cytoplasmic membrane-located barrier to the
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