Neomycin

Neomycin

Clinical data
Trade names	Neo-rx
AHFS/Drugs.com	Monograph
MedlinePlus	a682274
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Topical, oral
ATC code	A01AB08 (WHO) A07AA01 (WHO), B05CA09 (WHO), D06AX04 (WHO), J01GB05 (WHO), R02AB01 (WHO), S01AA03 (WHO), S02AA07 (WHO), S03AA01 (WHO)
Legal status
Legal status	US: ℞-only but OTC in Neosporin and similar ointments
Pharmacokinetic data
Bioavailability	None
Protein binding	N/A
Metabolism	N/A
Biological half-life	2 to 3 hours
Identifiers
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
CAS Number	1404-04-2 Y
PubChem CID	8378
IUPHAR/BPS	709
DrugBank	DB00994 Y
ChemSpider	8075 Y
UNII	I16QD7X297
KEGG	D08260 Y
ChEBI	CHEBI:7508 Y
ChEMBL	CHEMBL449118 N
ECHA InfoCard	100.014.333
Chemical and physical data
Formula	C23H46N6O13
Molar mass	614.644 g/mol
3D model (Jmol)	Interactive image
SMILES 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 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
NY (what is this?)

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. Neomycin belongs to aminoglycoside class of antibiotics that contain two or more aminosugars connected by glycosidic bonds.

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.

Neomycin resistance is conferred by either one of two aminoglycoside phosphotransferase genes. 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.