Skip to Content
Merck
CN

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

Sign Into View Organizational & Contract Pricing

Select a Size

About This Item

Linear Formula:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
CAS Number:
56-75-7
Molecular Weight:
323.13
Beilstein:
2225532
EC Number:
200-287-4
MDL number:
MFCD00078159
UNSPSC Code:
12352200
PubChem Substance ID:
24892868

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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)

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Danger

Hazard Statements

H318,H351,H361fd

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

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

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.
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
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.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service