Apramycin

Apramycin
Clinical data
Trade names	Apralan
Other names	Nebramycin II
AHFS/Drugs.com	International Drug Names
ATCvet code	QA07AA92 (WHO) QJ01GB90 (WHO) QJ51GB90 (WHO);
Legal status
Legal status	CA: ℞-only;
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-dihydroxycyclohexyl]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 (nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.^[2]

^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
^ 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.