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C6455

Sigma-Aldrich

Chloramphenicol

Sigma Reference Standard, powder

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
Beilstein/REAXYS Number:
2225532
EC Number:
200-287-4
MDL number:
MFCD00078159
UNSPSC Code:
12352200
PubChem Substance ID:
24892868

grade

Sigma Reference Standard

form

powder

packaging

vial of 200 mg

color

white

mp

149-153 °C (lit.)

antibiotic activity spectrum

viruses

mode of action

protein synthesis | interferes

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)

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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

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
067K5014
086K8803
046K8803
055K8804
103K8800

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Anthony J Brzoska et al.
PloS one, 8(2), e56090-e56090 (2013-02-15)
Members of the genus Acinetobacter have been the focus recent attention due to both their clinical significance and application to molecular biology. The soil commensal bacterium Acinetobacter baylyi ADP1 has been proposed as a model system for molecular and genetic
Uwe Richter et al.
Current biology : CB, 23(6), 535-541 (2013-03-05)
Proliferating cells require coordinated gene expression between the nucleus and mitochondria in order to divide, ensuring sufficient organelle number in daughter cells [1]. However, the machinery and mechanisms whereby proliferating cells monitor mitochondria and coordinate organelle biosynthesis remain poorly understood.
J N de Almeida Júnior et al.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 20(8), 784-790 (2013-12-21)
Trichosporon spp. have recently emerged as significant human pathogens. Identification of these species is important, both for epidemiological purposes and for therapeutic management, but conventional identification based on biochemical traits is hindered by the lack of updates to the species
David G Kirk et al.
Applied and environmental microbiology, 80(16), 5141-5150 (2014-06-15)
Clostridium botulinum produces heat-resistant endospores that may germinate and outgrow into neurotoxic cultures in foods. Sporulation is regulated by the transcription factor Spo0A and the alternative sigma factors SigF, SigE, SigG, and SigK in most spore formers studied to date.
David H Kwan et al.
Journal of the American Chemical Society, 137(17), 5695-5705 (2015-04-15)
Blood transfusions are critically important in many medical procedures, but the presence of antigens on red blood cells (RBCs, erythrocytes) means that careful blood-typing must be carried out prior to transfusion to avoid adverse and sometimes fatal reactions following transfusion.
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