Azidamfenicol

Chemical compound

S01AA25 (WHO)

Legal statusLegal status

In general: ℞ (Prescription only)

Identifiers

IUPAC name

2-azido-N-((1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide

CAS Number

13838-08-9^N

PubChem CID

62858

ChemSpider

56590^Y

UNII

40257685LM

KEGG

D07411^Y

ChEMBL

ChEMBL278788^N

CompTox Dashboard (EPA)

DTXSID90160647

ECHA InfoCard100.034.125

Chemical and physical dataFormulaC₁₁H₁₃N₅O₅Molar mass295.255 g·mol⁻¹3D model (JSmol)

Interactive image

Melting point99 to 107 °C (210 to 225 °F)

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

^NY (what is this?) (verify)

Azidamfenicol is an amphenicol antibiotic,^[1] which has similar profile to chloramphenicol. It is used only topically, as eye drops and ointment for treatment of susceptible bacterial infections.^[2]

References

^ de Groot AC (2021). "Chaper 3.26: Azidamfenicol". Topical Drugs. Monographs in Contact Allergy. Vol. 3 (First ed.). Boca Raton, FL: CRC Press. p. 79. ISBN 978-1-00-036786-7.
^ Sweetman SC (2007). Martindale: The Complete Drug Reference (35th ed.). London: Pharmaceutical Press. ISBN 978-0-85369-687-2.

Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Boromycin Carbomycin Carrimycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Gamithromycin Josamycin Kitasamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Solithromycin Spiramycin Telithromycin Tildipirosin Tilmicosin Troleandomycin Tulathromycin Tylosin Tylvalosin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)