Neomycin

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Neomycin
Neomycin B C.svg
Neomycin ball-and-stick.png
Systematic (IUPAC) name
(2RS,3S,4S,5R)-5-amino-2-(aminomethyl)-6-((2R,3S,4R,5S)-5-((1R,2R,5R,6R)-3,5-diamino-2-((2R,3S,4R,5S)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yloxy)-6-hydroxycyclohexyloxy)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yloxy)tetrahydro-2H-pyran-3,4-diol
Clinical data
Trade names Neo-rx
AHFS/Drugs.com monograph
MedlinePlus a682274
Pregnancy
category
  • US: D (Evidence of risk)
Legal status
Routes of
administration		 Topical, oral
Pharmacokinetic data
Bioavailability None
Protein binding N/A
Metabolism N/A
Biological half-life 2 to 3 hours
Identifiers
CAS Number 1404-04-2 YesY
ATC code A01AB08 (WHO) A07AA01, B05CA09, D06AX04, J01GB05, R02AB01, S01AA03, S02AA07, S03AA01
PubChem CID: 8378
IUPHAR/BPS 709
DrugBank DB00994 YesY
ChemSpider 8075 YesY
UNII I16QD7X297 YesY
KEGG D08260 YesY
ChEBI CHEBI:7508 YesY
ChEMBL CHEMBL449118 N
Chemical data
Formula C23H46N6O13
Molecular mass 614.644 g/mol
  • O([C@H]3[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@H]1O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]1N)[C@H]2O)[C@@H](O)[C@H](N)C[C@@H]3N)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4N)CN
  • InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7+,8?,9+,10+,11-,12+,13+,14-,15+,16-,17+,18-,19+,20-,21+,22-,23-/m0/s1 N
  • Key:PGBHMTALBVVCIT-DPNHOFNISA-N N
 NYesY (what is this?)  (verify)

Neomycin is an aminoglycoside antibiotic found in many topical medications such as creams, ointments, and eyedrops. The discovery of neomycin dates back to 1949. It was discovered in the lab of Selman Waksman, who was later awarded the Nobel Prize in Physiology or Medicine in 1951. Neomycin belongs to aminoglycoside class of antibiotics that contain two or more aminosugars connected by glycosidic bonds.

Uses

Neomycin is typically used as a topical preparation, such as Neosporin. It can also be given orally, where it is usually combined with other antibiotics. Neomycin is not absorbed from the gastrointestinal tract and has been used as a preventive measure for hepatic encephalopathy and hypercholesterolemia. By killing bacteria in the intestinal tract, it keeps ammonia levels low and prevents hepatic encephalopathy, especially prior to GI surgery. It has also been used to treat small intestinal bacterial overgrowth. It is not given via injection, as neomycin is extremely nephrotoxic (causes kidney damage), even when compared to other aminoglycosides. The exception is when neomycin is included, in very small quantities, as a preservative in some vaccines – typically 0.025 mg per dose.[1]

Molecular biology

Neomycin resistance is conferred by either one of two aminoglycoside phosphotransferase genes.[2] A neo gene is commonly included in DNA plasmids used by molecular biologists to establish stable mammalian cell lines expressing cloned proteins in culture; many commercially available protein expression plasmids contain neo as a selectable marker. Non-transfected cells will eventually die off when the culture is treated with neomycin or similar antibiotic. Neomycin or kanamycin can be used for prokaryotes, but geneticin (G418) is, in general, needed for eukaryotes.

Spectrum

Similar to other aminoglycosides, neomycin has excellent activity against Gram-negative bacteria, and has partial activity against Gram-positive bacteria. It is relatively toxic to humans, and many people have allergic reactions to it.[3] See: Hypersensitivity. Physicians sometimes recommend using antibiotic ointments without neomycin, such as Polysporin.[4] The following represents MIC susceptibility data for a few medically significant Gram-negative bacteria.[5]

  • Enterobacter cloacae: >16 μg/ml
  • Escherichia coli: 1 μg/ml
  • Proteus vulgaris: 0.25 μg/ml

Composition

Standard grade neomycin is composed of a number of related compounds including neomycin A (neamine), neomycin B (framycetin), neomycin C, and a few minor compounds found in much lower quantities. Neomycin B is the most active component in neomycin followed by neomycin C and neomycin A. Neomycin A is an inactive degradation product of the C and B isomers.[6] The quantities of these components in neomycin vary from lot-to-lot depending on the manufacturer and manufacturing process.[7]

Safety

In 2005–06, neomycin was the fifth-most-prevalent allergen in patch test results (10.0%).[8]

History

Neomycin was discovered in 1949 by the microbiologist Selman Waksman and his student Hubert Lechevalier at Rutgers University. It is produced naturally by the bacterium Streptomyces fradiae.[9] Synthesis requires specific nutrient conditions in either stationary or submerged aerobic conditions. The compound is then isolated and purified from the bacterium.[10]

DNA binding

Aminoglycosides such as neomycin are known for their ability to bind to duplex RNA with high affinity. The association constant for neomycin with A-site RNA has been found to be in the 109 M−1 range.[11] However, more than 50 years after its discovery, its DNA-binding properties were still unknown. Neomycin has been shown to induce thermal stabilization of triplex DNA, while having little or almost no effect on the B-DNA duplex stabilization.[12] Neomycin was also shown to bind to structures that adopt A-form structure, triplex DNA being one of them. Neomycin also includes DNA:RNA hybrid triplex formation.[13]

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ DermNet dermatitis/neomycin-allergy
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ http://www.toku-e.com/Assets/MIC/Neomycin%20sulfate%20EP.pdf
  6. ↑ Cammack, R. Attwood, T. K. Campbell, P. N. Parish, J. H. Smith, A. D. Stirling, J. L. Vella, F. (2006). "Oxford Dictionary of Biochemistry and Molecular Biology (2nd Edition) – neomycin." Oxford University Press. (2006): 453. Knovel.com. Web. 18 Nov. 2014.
  7. ↑ Tsuji, Kiyoshi, and John H. Robertson. "Comparative Study of Responses to Neomycins B and C by Microbiological and Gas-Liquid Chromatographic Assay Methods."Applied Microbiology 18.3 (1969): 396–98. Nih.gov. Web. 23 Oct. 2013.
  8. ↑ Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS, Mathias CG, Deleo VA, Rietschel RL, Marks J. Patch-test results of the North American Contact Dermatitis Group 2005–2006. Dermatitis. 2009 May–Jun;20(3):149-60.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ "Neomycin." Pharmaceutical Manufacturing Encyclopedia (3rd edition) Volume 3. (2007): 2415–2416. Knovel.com. Web. 18 Nov. 2014.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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