Neomycin

Neomycin
Systematic (IUPAC) name
(1R,2R,3S,4R,6S)-4,6-diamino-2-
Clinical data
Trade names Neo-rx
AHFS/Drugs.com monograph
MedlinePlus a682274
Pregnancy cat.  ?
Legal status OTC
Routes Topical, Oral
Pharmacokinetic data
Half-life 2 to 3 hours
Identifiers
CAS number 1404-04-2
ATC code A01AB08 A07AA01, B05CA09, D06AX04, J01GB05, R02AB01, S01AA03, S02AA07, S03AA01
PubChem CID 8378
IUPHAR ligand 709
DrugBank DB00994
ChemSpider 8075
UNII I16QD7X297 YesY
KEGG D08260
ChEBI CHEBI:7508
ChEMBL CHEMBL449118
Chemical data
Formula C23H46N6O13 
Mol. mass 614.644 g/mol
SMILES eMolecules & PubChem

Neomycin is an aminoglycoside antibiotic that is 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 and medicine in 1951. Neomycin, belongs to aminoglycoside class of antibiotics which contain two or more aminosugars connected by glycosidic bonds. Neamine (two rings), Ribostamycin (three rings), Paromomycin (four rings) and Lividomycin (five rings) are some other examples of aminoglycosides. They have shown tremendous potential as antibacterials. One of them, Gentamicin has been used extensively in clinical practice. Due to the inherent oto and nephrotoxicity of these substances, systemic use has declined as safer alternatives have become available.

Contents

Uses

Neomycin is overwhelmingly 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 intravenously, as neomycin is extremely nephrotoxic (causes kidney damage), especially 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]

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.[5]

Neomycin as a DNA binder

Neomycin belongs to the family of aminoglycosides. This family includes many other medicinally important drugs: streptomycin, paromomycin and kanamycin . Aminoglycosides are known for their ability to bind to duplex RNA with high affinity. A study done by Daniel Pilch, Associate Professor Dept. of Pharmacology at Rutgers University, and his coworkers determined the association constant for neomycin with A-site RNA was found to be in the ~109 range. However, more than 50 years after its discovery, its DNA-binding properties were still unknown. In 2000, Dev P. Arya, currently Director of the Laboratory of Medicinal Chemistry at Clemson University, and his coworkers discovered that neomycin induces enormous thermal stabilization of triplex DNA while having little or almost no effect on the DNA duplex stabilization. They also showed that neomycin binds to structures that adopt A-form structure, triplex DNA being one of them. They later went on to show that neomycin even induces DNA:RNA hybrid triplex formation. [6]

References



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Look at other dictionaries:

  • Neomycin — См. Неомицин (Источник: «Словарь терминов микробиологии») …   Словарь микробиологии

  • neomycin — neomycin. См. неомицин. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • neomycin — [nē΄ō mī′sin, nē΄əmī′sin] n. [ NEO + MYCIN] a broad spectrum antibiotic obtained from an actinomycete (Streptomyces fradiae) and used in the treatment of various infections, esp. of the skin and eye …   English World dictionary

  • Neomycin — Strukturformel Allgemeines Freiname Neomycin Andere Namen …   Deutsch Wikipedia

  • neomycin — Either of two aminoglycosides (B and C) produced by Streptomyces fradiae that have generalized antibiotic activity. Neomycin A (Ineamine) contains 2 deoxy 1,3 diamino inositol combined with the aminoglycoside …   Dictionary of molecular biology

  • Neomycin — Ne|o|my|cin [↑ neo (1) u. mycin], das; s, e: aus Streptomyceskulturen isolierbares u. gegen bakterielle Infektionen lokal einsetzbares Gemisch von Aminoglykosid Antibiotika. * * * NeoMycin,   ein medizinisches Expertensystem …   Universal-Lexikon

  • neomycin — neo·my·cin .nē ə mīs ən n a broad spectrum highly toxic mixture of aminoglycoside antibiotics produced by a bacterium of the genus Streptomyces (S. fradiae) specif a commercial preparation that is composed chiefly of two stereoisomers of neomycin …   Medical dictionary

  • neomycin — noun Date: 1949 a broad spectrum highly toxic antibiotic or mixture of antibiotics produced by a streptomyces (Streptomyces fradiae) and used medically especially to treat local infections …   New Collegiate Dictionary

  • neomycin — /nee oh muy sin/, n. Pharm. an antibiotic produced by an actinomycete, Streptomyces fradiae, administered orally or locally, used chiefly for skin, urinary tract, and eye infections and as a surgical antiseptic. [1945 50; NEO + MYCIN] * * * …   Universalium

  • neomycin — noun A broad spectrum aminoglycoside antibiotic that is found in many topical medications …   Wiktionary


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