Apramycin

Title: Apramycin
CAS Registry Number: 37321-09-8
CAS Name: O-4-Amino-4-deoxy-a-D-glucopyranosyl-(1®8)-O-(8R)-2-amino-2,3,7-trideoxy-7-(methylamino)-D-glycero-a-D-allo-octodialdo-1,5:8,4-dipyranosyl-(1®4)-2-deoxy-D-streptamine
Additional Names: 4-O-[3a-amino-6a-[(4-amino-4-deoxy-a-D-glucopyranosyl)oxy]-2,3,4,4ab,6,7,8aa-octahydro-8b-hydroxy-7b-(methylamino)pyranopyrano[3,2-b]pyran-2a-yl]-2-deoxy-D-streptamine; nebramycin factor 2
Manufacturers' Codes: EL-857; EL-857/820; 47657
Trademarks: Apralan (Elanco)
Molecular Formula: C21H41N5O11
Molecular Weight: 539.58
Percent Composition: C 46.74%, H 7.66%, N 12.98%, O 32.62%
Literature References: Broad spectrum aminocyclitol antibiotic and component of the nebramycin complex, produced by a strain of Streptomyces tenebrarius: R. Q. Thompson, E. A. Presti, Antimicrob. Agents Chemother. 1967, 332; W. M. Stark, US 3691279 (1972 to Lilly). Structure, abs config and properties: S. O'Connor et al., J. Org. Chem. 41, 2087 (1976). 13C-NMR: E. Wenkert, E. W. Hagaman, ibid. 701. In vitro activity: R. Ryden et al., J. Antimicrob. Chemother. 3, 609 (1977). Synthetic studies: H. C. Jarrell, W. A. Szarek, Carbohydr. Res. 67, 43 (1978); eidem, Can. J. Chem. 56, 144 (1978); 57, 924 (1979). See also tobramycin.
Derivative Type: Monohydrate
Properties: From aqueous ethanol, mp 245-247°. pKa (H2O): 8.5, 7.8, 7.2, 6.2, 5.4. Very soluble in water; slightly sol in lower alcohols.
Melting point: mp 245-247°
pKa: pKa (H2O): 8.5, 7.8, 7.2, 6.2, 5.4
Therap-Cat-Vet: Antibacterial.
Aprepitant Aprindine Aprinocarsen Aprobarbital Apronalide

Apramycin
Apramycin.svg
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 37321-09-8 N
ATCvet code QA07AA92 QJ01GB90 QJ51GB90
PubChem CID 3081545
DrugBank DB04626
ChemSpider 2339128 YesY
UNII 388K3TR36Z YesY
KEGG D02322 YesY
ChEBI CHEBI:2790 YesY
ChEMBL CHEMBL1230961 N
Chemical data
Formula C21H41N5O11 
Mol. mass 539.58 g/mol
 N (what is this?)  (verify)

Apramycin (also Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.[1]