azidamfenicol

• CAT Number: M058985
• CAS Number: 13838-08-9
• Molecular Formula: C11H13N5O5
• Molecular Weight: 295.255
• Purity: 99%
• Storage: Store at -20°C
• Analysis method: HPLC
• IUPAC Name: 2-azido-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• InChI: InChI=1S/C11H13N5O5/c12-15-13-5-10(18)14-9(6-17)11(19)7-1-3-8(4-2-7)16(20)21/h1-4,9,11,17,19H,5-6H2,(H,14,18)/t9-,11-/m1/s1
• InChIKey: SGRUZFCHLOFYHZ-MWLCHTKSSA-N
• SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)CN=[N+]=[N-])O)[N+](=O)[O-]

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.

Reference

1-p-Nitrophenyl-2-azidoacetylaminopropane derivatives. Meiser W. & Domagk G. 1959 US Patent 2,882,275.