Apramycin  (Synonyms: Nebramycin II)

Apramycin (Nebramycin II) is an orally active, acidic pH tolerant and aminoglycoside-modifying-enzymes-tolerant aminoglycoside antibiotic which inhibits protein biosynthesis by targeting the bacterial ribosome. Apramycin is a potential anti-drug-resistance antibiotic^[1][2][3].

Apramycin (4 mg/L) inhibits 99% of K. pneumoniae and 93% of Enterobacter clinical isolates. Apramycin (8 mg/L) inhibits 99% of all E. coli, 98% of C. freundii, 96% of Providencia spp., 92% of S. marcescens, 97% of M. morganii and 100% of P. mirabilis clinical isolates, exhibiting significantly better antimicrobial activity than the clinical standard-of-care aminoglycosides Gentamicin and Amikacin^[1].
Apramycin (100 μM, 10 min) exerts an 11% decrease in cytoplasmic uptake of E.coli when lowering the pH from 7.3 to 5.7 while the amounts of Gentamicin and Amikacin are reduced by 62% and 51%, respectively^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Apramycin (200 mg/kg/d, s.c., 9 d) demonstrates significant in vivo efficacy in lungs of M. tuberculosis low-dose aerosol infection model IFN-γ knockout mice^[2].
Apramycin (16, 32, 80 mg/kg, s.c., 24 h) dose-dependently reduces bacterial burden in the kidneys between 2-5 log₁₀ and in blood between 2-3 log₁₀ for neutropenic model of Staphylococcus aureus septicemia mice^[2].
Apramycin (50 mg/kg/d, s.c., 21 d) induces nephrotoxicity scores comparable to those induced by Gentamicin (10 mg/kg/d)^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

539.58

C₂₁H₄₁N₅O₁₁

37321-09-8

Solid

White to light yellow

O[C@H]1[C@](O[C@H](O[C@@]([C@H](C[C@H]2N)N)([H])[C@@H]([C@H]2O)O)[C@H](N)C3)([H])[C@@]3([H])O[C@H](O[C@@]([C@@H]([C@@H](O)[C@@H]4N)O)([H])O[C@@H]4CO)[C@H]1NC

Room temperature in continental US; may vary elsewhere.

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

• [1]. Juhas M, et al. In vitro activity of apramycin against multidrug-, carbapenem- and aminoglycoside-resistant Enterobacteriaceae and Acinetobacter baumannii. J Antimicrob Chemother. 2019;74(4):944-952.  [Content Brief]

  [2]. Meyer M, et al. In vivo efficacy of apramycin in murine infection models. Antimicrob Agents Chemother. 2014 Nov;58(11):6938-41.  [Content Brief]

  [3]. Becker K, et al. Antibacterial activity of apramycin at acidic pH warrants wide therapeutic window in the treatment of complicated urinary tract infections and acute pyelonephritis. EBioMedicine. 2021 Nov;73:103652.  [Content Brief]