Apramycin

Apramycin
Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	QA07AA92 (WHO) QJ01GB90 (WHO) QJ51GB90 (WHO);
Identifiers
	IUPAC name (2R,3R,4R,5S,6R)-5-amino-2- [((1R,2R,3R,4R,6R,8R)-8-amino-9- [(1R,2S,3R,4R,6R)-4,6-diamino-2,3- dihydroxy-cyclohexyl]oxy-2-hydroxy- 3-methylamino-5,10- dioxabicyclo[4.4.0]dec-4-yl)oxy]-6- (hydroxymethyl)oxane-3,4-diol;
CAS Number	37321-09-8 ;
PubChem CID	3081545;
DrugBank	DB04626 ;
ChemSpider	2339128 ;
UNII	388K3TR36Z;
KEGG	D02322 ;
ChEBI	CHEBI:2790 ;
ChEMBL	ChEMBL1230961 ;
CompTox Dashboard (EPA)	DTXSID5045465 ;
ECHA InfoCard	100.048.582
Chemical and physical data
Formula	C21H41N5O11
Molar mass	539.583 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O3[C@H](O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O)[C@@H](NC)[C@@H](O)[C@H]4O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)C[C@H]34;
	InChI InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1 ; Key:XZNUGFQTQHRASN-XQENGBIVSA-N ;
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Apramycin (also Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.[1]

Spectrum of bacterial susceptibility and resistance

Apramycin can be used to treat bacterial infections in animals caused by Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa. The following shows susceptibility data on medically significant organisms:

Escherichia coli - 1 μg/mL - >512 μg/mL (this large range may be due to resistant organisms, typical MIC values are likely in the range of 2 -8 μg/mL.
Klebsiella pneumoniae - 2 μg/mL - >256 μg/mL
Pseudomonas aeruginosa - 4 μg/mL[2]

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References

Ryden R, Moore BJ (November 1977). "The in vitro activity of apramycin, a new aminocyclitol antibiotic". The Journal of Antimicrobial Chemotherapy. 3 (6): 609–613. doi:10.1093/jac/3.6.609. PMID 340441.
"Apramycin". KnowledgeBase: The Antimicrobial Index.

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[1] Ryden R, Moore BJ (November 1977). "The in vitro activity of apramycin, a new aminocyclitol antibiotic". The Journal of Antimicrobial Chemotherapy. 3 (6): 609–613. doi:10.1093/jac/3.6.609. PMID 340441.

[2] "Apramycin". KnowledgeBase: The Antimicrobial Index.