azidamfenicol

azidamfenicol Basic information
Product Name:azidamfenicol
Synonyms:azidamfenicol;AZIAMPHENICOL, PHARMA;azidoamphenicol;2-Azido-N-[(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-nitrophenyl)ethyl]acetamide;AzidoaMphenicol, LeukoMycin N;2-azido-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide;azidamfenicol ISO 9001:2015 REACH;Antibiotic,Bacterial,bacteria,Azidamfenicol,Inhibitor,peptidyltransferase,Gram-positive,Gram-negative,inhibit,ribosomal
CAS:13838-08-9
MF:C11H13N5O5
MW:295.254
EINECS:2375529
Product Categories:
Mol File:13838-08-9.mol
azidamfenicol Structure
azidamfenicol Chemical Properties
Melting point 107°
alpha D20 -20° (c = 1.6 in ethyl acetate)
storage temp. -20°C Freezer, Under inert atmosphere
solubility Ethyl Acetate (Slightly, Sonicated), Methanol (Slightly)
form Solid
color White to Off-White
Safety Information
MSDS Information
azidamfenicol Usage And Synthesis
OriginatorBerlicetin-,Chauvin
UsesAzidamfenicol is a semi-synthetic chloramphenicol in which the nitro moiety is replaced with a methylsulphone and the dichloroacetamide is replaced with azidoacetamide, first synthesised at Bayer in 1959. Azidamfenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Azidamfenicol acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Azidamfenicol has received little research attention with only a few literature citations.
DefinitionChEBI: Azidamfenicol is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
Manufacturing Process21.2 g of D-(-)-threo-1-p-nitrophenyl-2-aminopropane-1,3-diol are stirred with 10 g of azidoacetonitrile (B.P. 68°C/25 mm) in a mixture of 125 ml of methanol and 125 ml of water at 30-40°C for a few days. The mixture is filtered off from a little undissolved base and the solvent is distilled in vacuo. The residue is treated with a little normal hydrochloric acid until acid to Congo red and extracted with ethylacetate. By evaporating the solvent and recrystallizing the residue from ethylene chloride is obtained D-(-)-threo-1-pnitrophenyl- 2-azidoacetylamino-propane-1,3-diol, M.P. 107°C.
Therapeutic FunctionAntibiotic
azidamfenicol Preparation Products And Raw materials
Raw materials4-Bromo-5-methylresorcinol-->Hydrochloric acid-->Acetonitrile, 2-azido-
Ethyl acetate 2-Amino-1-(4-nitrophenyl)-1,3-propanediol Chloramphenicol azidamfenicol

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