Apramycin

Chemical compound

QA07AA92 (WHO) QJ01GB90 (WHO) QJ51GB90 (WHO)

Legal statusLegal status

CA: ℞-only^[1]

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

KEGG

D02322^Y

ChEBI

CHEBI:2790^Y

ChEMBL

ChEMBL1230961^N

CompTox Dashboard (EPA)

DTXSID5045465

ECHA InfoCard100.048.582

Chemical and physical dataFormulaC₂₁H₄₁N₅O₁₁Molar mass539.583 g·mol⁻¹3D 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^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.^[2]

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.^{[citation needed]} 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^[3]

References

^ "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.
^ "Apramycin". KnowledgeBase: The Antimicrobial Index.

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

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
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
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

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