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^N
PubChem (CID)	3081545
DrugBank	DB04626^Y
ChemSpider	2339128^Y
UNII	388K3TR36Z^Y
KEGG	D02322^Y
ChEBI	CHEBI:2790^Y
ChEMBL	CHEMBL1230961^N
Chemical and physical data
Formula	C₂₁H₄₁N₅O₁₁
Molar mass	539.58 g/mol
3D model (Jmol)	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^Y Key:XZNUGFQTQHRASN-XQENGBIVSA-N^Y
^NY (what is this?) (verify)

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]

References

↑ R. Ryden; B. J. Moore (1977). "The in vitro activity of apramycin, a new aminocyditol antibiotic". J Antimicrob Chemother. 3 (6): 609–613. doi:10.1093/jac/3.6.609. PMID 340441.
↑ http://antibiotics.toku-e.com/antimicrobial_1728.html

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Plazomicin^† Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

Fluorocyclines	Eravacycline^†

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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