Azidamfenicol

Azidamfenicol
Systematic (IUPAC) name

2-azido-N-((1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Topical (ocular)
Legal status	Prescription only
Identifiers
CAS Number	13838-08-9^N
ATC code	S01AA25 (WHO)
PubChem	CID 62858
ChemSpider	56590^Y
UNII	40257685LM^Y
KEGG	D07411^Y
ChEMBL	CHEMBL278788^N
Chemical data
Formula	C₁₁H₁₃N₅O₅
Molar mass	295.251 g/mol
SMILES [N-]=[N+]=N\CC(=O)N[C@@H]([C@H](O)c1ccc([N+]([O-])=O)cc1)CO
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^Y Key:SGRUZFCHLOFYHZ-MWLCHTKSSA-N^Y
Physical data
Melting point	99 to 107 °C (210 to 225 °F)
^NY (what is this?) (verify)

Azidamfenicol is an amphenicol antibiotic, which has similar profile to chloramphenicol. It is used only topically, as eye drops and ointment for treatment of susceptible bacterial infections.^[1]

References

↑ Martindale, 35th Edition, 2006

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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