Apramycin

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Apramycin
Apramycin.svg
Clinical data
Trade names Apralan
AHFS/Drugs.com International Drug Names
ATCvet code
Legal status
Legal status
Identifiers
  • (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
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PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.048.582 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H41N5O11
Molar mass 539.583 g·mol−1
3D model (JSmol)
  • 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=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 Yes check.svgY
  • Key:XZNUGFQTQHRASN-XQENGBIVSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Apramycin (also Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius . [2]

Contents

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:

Mechanism of action

Traditional knowledge suggests that aminoglycosides bind to the bacterial ribosome, leading to misreading of mRNA and incorporation of incorrect amino acids in the nascent polypeptide chain. However, aminoglycosides, including apramycin, have been shown to not only cause misreading of the genetic code but also significantly slow down the overall rate of protein synthesis in live bacterial cells [4] . This dual effect on both accuracy and efficiency of protein synthesis helps to explain the bactericidal properties of apramycin.

Related Research Articles

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Beta-lactamases (β-lactamases) are enzymes produced by bacteria that provide multi-resistance to beta-lactam antibiotics such as penicillins, cephalosporins, cephamycins, monobactams and carbapenems (ertapenem), although carbapenems are relatively resistant to beta-lactamase. Beta-lactamase provides antibiotic resistance by breaking the antibiotics' structure. These antibiotics all have a common element in their molecular structure: a four-atom ring known as a beta-lactam (β-lactam) ring. Through hydrolysis, the enzyme lactamase breaks the β-lactam ring open, deactivating the molecule's antibacterial properties.

<span class="mw-page-title-main">Gram-negative bacteria</span> Group of bacteria that do not retain the Gram stain used in bacterial differentiation

Gram-negative bacteria are bacteria that unlike gram-positive bacteria do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is their cell envelope, which consists of a thin peptidoglycan cell wall sandwiched between an inner (cytoplasmic) membrane and an outer membrane. These bacteria are found in all environments that support life on Earth.

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<span class="mw-page-title-main">Colistin</span> Antibiotic

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<span class="mw-page-title-main">Bacterial pneumonia</span> Disease of the lungs

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<span class="mw-page-title-main">Ceftazidime</span> Antibiotic medication

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<span class="mw-page-title-main">Kanamycin A</span> Antibiotic

Kanamycin A, often referred to simply as kanamycin, is an antibiotic used to treat severe bacterial infections and tuberculosis. It is not a first line treatment. It is used by mouth, injection into a vein, or injection into a muscle. Kanamycin is recommended for short-term use only, usually from 7 to 10 days. Since antibiotics only show activity against bacteria, it is ineffective in viral infections.

<span class="mw-page-title-main">Tigecycline</span> Chemical compound

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<span class="mw-page-title-main">Cefotaxime</span> Chemical compound

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<span class="mw-page-title-main">Azlocillin</span> Antibiotic

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<span class="mw-page-title-main">Enrofloxacin</span> Chemical compound

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<span class="mw-page-title-main">Ecthyma gangrenosum</span> Medical condition

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<span class="mw-page-title-main">Ceftolozane/tazobactam</span> Antibiotic

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<span class="mw-page-title-main">Cefiderocol</span> Antibiotic

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References

  1. "Health product highlights 2021: Annexes of products approved in 2021". Health Canada . 3 August 2022. Retrieved 25 March 2024.
  2. 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.
  3. "Apramycin". KnowledgeBase: The Antimicrobial Index.
  4. Aguirre Rivera, Javier; Larsson, Jimmy; Volkov, Ivan L.; Seefeldt, A. Carolin; Sanyal, Suparna; Johansson, Magnus (2021-03-02). "Real-time measurements of aminoglycoside effects on protein synthesis in live cells". Proceedings of the National Academy of Sciences. 118 (9). Bibcode:2021PNAS..11813315A. doi: 10.1073/pnas.2013315118 . ISSN   0027-8424. PMC   7936356 . PMID   33619089.