| Identification | Back Directory | [Name]
azidamfenicol | [CAS]
13838-08-9 | [Synonyms]
azidamfenicol
azidoamphenicol
AZIAMPHENICOL, PHARMA
AzidoaMphenicol, LeukoMycin N
azidamfenicol ISO 9001：2015 REACH
2-azido-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
2-Azido-N-[(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-nitrophenyl)ethyl]acetamide | [EINECS(EC#)]
237-552-9 | [Molecular Formula]
C11H13N5O5 | [MDL Number]
MFCD00866215 | [MOL File]
13838-08-9.mol | [Molecular Weight]
295.254 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [Originator]
Berlicetin-,Chauvin | [Uses]
Azidamfenicol 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. | [Definition]
ChEBI: Azidamfenicol is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid. | [Manufacturing Process]
21.2 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 Function]
Antibiotic |
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