Description
Chloramphenicol, 25 G
≥98% (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
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
PubChem Substance ID:
24892250
NACRES:
NA.76
PROPERTIES
assay
≥98% (HPLC)
form
powder or crystals
pKa
5.5
mp
148-150 °C (lit.)
antibiotic activity spectrum
Gram-negative bacteria
Gram-positive bacteria
mycobacteria
mycoplasma
mode of action
protein synthesis | interferes
storage temp.
room temp
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 10-20μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.
Chloramphenicol has been used as a bacteriostatic non potent antibiotic.[1] It has been used for the selection/growth of positive bacterial cells.[2][3]
Chloramphenicol has been used as a bacteriostatic non potent antibiotic.[1] It has been used for the selection/growth of positive bacterial cells.[2][3]
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 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
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.
SAFETY INFORMATION
signalword
Danger
hcodes
H318 - H351 - H361fd
pcodes
P202 - P280 - P305 + P351 + P338 - P308 + P313 - P405 - P501
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Repr. 2
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges