Azidamfenicol: Difference between revisions

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	<!--Identifiers-->		<!--Identifiers-->
	\| CAS_number = 13838-08-9		\| CAS_number = <!-- blanked - oldvalue: 13838-08-9 -->
	\| ATC_prefix = S01		\| ATC_prefix = S01
	\| ATC_suffix = AA25		\| ATC_suffix = AA25
			\| StdInChI = 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
			\| StdInChIKey = SGRUZFCHLOFYHZ-MWLCHTKSSA-N
	\| PubChem = 62858		\| PubChem = 62858
	\| ChemSpiderID = 56590		\| ChemSpiderID = 56590
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	\| UNII = 40257685LM		\| UNII = 40257685LM
	\| KEGG = D07411		\| KEGG = D07411
	\| ChEMBL = 278788		\| ChEMBL = <!-- blanked - oldvalue: 278788 -->

	<!--Chemical data-->
	\| C=11 \| H=13 \| N=5 \| O=5		\| C=11 \| H=13 \| N=5 \| O=5
	\| molecular_weight = 295.251 g/mol		\| molecular_weight = 295.251 g/mol

Revision as of 13:04, 4 November 2011

Pharmaceutical compound

Azidamfenicol
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Topical (ocular)
ATC code	S01AA25 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 2-azido-N-((1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide
PubChem CID	62858
ChemSpider	56590
UNII	40257685LM
KEGG	D07411
CompTox Dashboard (EPA)	DTXSID90160647
ECHA InfoCard	100.034.125
Chemical and physical data
Formula	C₁₁H₁₃N₅O₅
Molar mass	295.251 g/mol g·mol
3D model (JSmol)	Interactive image
Melting point	99 to 107 °C (210 to 225 °F)
SMILES ==N\CC(=O)N((O)c1ccc(()=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 Key:SGRUZFCHLOFYHZ-MWLCHTKSSA-N

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.

References

Martindale, 35th Edition, 2006

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

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)

Neomycin

Kanamycin

-micin (Micromonospora)

Gentamicin

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

MLS (transpeptidation/translocation)

Macrolides	Azithromycin Boromycin Carbomycin Carrimycin Clarithromycin Dirithromycin Erythromycin Flurithromycin Gamithromycin Josamycin Kitasamycin Midecamycin Miocamycin Nafithromycin 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)

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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