Neomycin

Structural formula
General
Non-proprietary name	Neomycin ( INN )
other names	O -2,6-diamino-2,6-dideoxy- α - D -glucopyranosyl- (1 → 4) - O - [ O -2,6-diamino-2,6-dideoxy- β - L -idopyranosyl- ( 1 → 3) - β - D -ribofuranosyl- (1 → 5)] - 2-deosxy- D -streptamine (2 S , 3 R , 4 R , 5 R , 6 R ) -5-Amino-2- (aminomethyl) -6 - [(2 R , 3 R , 4 R , 5 S ) -5 - [(1 S. , 2 R , 3 S , 5 R , 6 S ) -3,5-diamino-2 - [(2 R , 3 R , 4 R , 5 R , 6 R ) -3-amino-6- (aminomethyl) - 4,5-dihydroxy-oxan-2-yl] oxy-6-hydroxy-cyclohexyl] oxy-4-hydroxy-2- (hydroxymethyl) oxolan-3-yl] oxy-oxane-3,4-diol
Molecular formula	C 23 H 46 N 6 O 13
External identifiers / databases
CAS number 1404-04-2 EC number 215-766-3 ECHA InfoCard 100.014.333 PubChem 8378 ChemSpider 8075 DrugBank DB00994 Wikidata Q423098
Drug information
ATC code	J01 GB05 A01 AB08 A07 AA01 B05 CA09 B06 AC04 G01 AA14 R02 AB01 S01 AA03 S02 AA07 S03 AA01
Drug class	Antibiotic , aminoglycosides
properties
Molar mass	614.64 g mol −1
solubility	soluble in water (6 g l −1 as sulfate)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 361-373 P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Neomycin is a broad spectrum antibiotic from the aminoglycoside group, particularly against gram-negative but also gram-positive bacteria . It is very similar to the aminoglycoside antibiotic paromomycin .

chemistry

Neomycin was first isolated in 1949 in the group of Selman Waksman from Streptomycetes ( Streptomyces fradiae ). Neomycin consists of three components: Neomycin A ( Neamin ), Neomycin B ( Framycetin , Soframycin "Dembach-Roussel" "" from, first presented in 1947) and Neomycin C. (The first commercial forms of Neomycin were Bykomycin from Byk Gulden and Myacyne from OWG- Chemistry ). The main component Neomycin B and Neomycin C are stereoisomers . Neomycin A is an ineffective hydrolytic degradation product of both isomers.

Mechanism of action

Neomycin blocks protein synthesis in susceptible bacteria by attaching to the 30S subunit of the 70S ribosomes. There is complete cross-resistance with kanamycin , and in some cases with gentamicin .

Areas of application and preparations

Human medicine

Neomycin is used as a sulfate salt only locally for skin and mucous membrane infections , wounds and burns in the form of drops, creams and ointments. For the treatment of bladder and urinary tract infections with catheter wearers or after urological operations, sterile solutions are available for instillation into the urinary bladder . Neomycin can also be used to treat hepatic encephalopathy : When administered orally  , neomycin is effective in the intestine and kills ammonia-forming bacteria there. However, the severe side effects limit the therapy.

In addition to the use in monopreparations, it occurs in numerous combination preparations.

Veterinary medicine

In addition to treating skin diseases, mastitis and eye infections, neomycin is also used in domestic animals to treat diseases of the gastrointestinal tract , as only about 3% of it is absorbed in the intestine.

Contraindications and side effects

Neomycin is relatively toxic and must not be used in neomycin-sensitive patients or in larger wounds. A combination with other aminoglycoside and neurotoxic antibiotics should also be avoided.

Particularly noteworthy is the ototoxicity (damage to the inner ear) of locally and topically applied aminoglycoside antibiotics such as neomycin, kanamycin and framycetin. Even very small amounts that reach the inner ear and penetrate the hair cells of the cochlea can lead to an irreparable (!) Loss of sensory hair, with the result of hearing loss up to complete deafness and massive balance problems. Since z. B. Neomycin is used in ear drops, these drops must never be used in the ear canal with a perforated eardrum.

When applied superficially, allergic reactions can (rarely) occur.

Trade names

Monopreparations

Cysto-Myacyne (D), Myacyne (D), Uro-Nebacetin (D), Vagicillin (D)

Combination preparations

Baneocin (A), Baneopol (CH), Betnovate (CH), Cicatrx (CH), Cortidexason comp. (D), Cortifluid (CH), Dermamycin (D), Dexa-Polyspectran (D), Dispadex comp. (D), FML-Neo (CH), Isopto-Max (D), Jellin-Neomycin (D), Maxitrol (CH), Mycinopred (CH), Mycolog (CH), Nebacetin (D), Néocônes (CH), Neo-Hydro (CH), Neosporin (CH), Neotracin (CH), Otosporin (CH), Panotile (CH), Pivalone comp. (CH), POlydexa (CH), Polyspectran (D), Spersapolymyxin (CH), Synalar (CH), Topsym polyvalent (CH),

Individual evidence

1. ^ Entry on neomycin in the DrugBank of the University of Alberta .
2. ↑ There is not yet a harmonized classification for this substance . A labeling of neomycin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on February 3, 2020, is reproduced from a self-classification by the distributor .
3. ↑ Selman Abraham Waksman, HA Lechevalier: Neomycin, a New Antibiotic Active against Streptomycin-Resistant Bacteria, including Tuberculosis Organisms. In: Science. Vol. 109 (2830), 1949, pp. 305-307. PMID 17782716
4. ↑ Karl Wurm, AM Walter: Infectious Diseases. In: Ludwig Heilmeyer (ed.): Textbook of internal medicine. Springer-Verlag, Berlin / Göttingen / Heidelberg 1955; 2nd edition, ibid. 1961, pp. 9–223, here: p. 54.
5. ↑ Patidar, KR, & Bajaj, JS (2013). Antibiotics for the Treatment of Hepatic Encephalopathy. In: Metabolic Brain Disease. 28 (2), 307-312. PMC 3654040 (free full text)
6. ↑ Aktories, Förstermann, Hofmann Starke: General and special pharmacology and toxicology , 10th edition, p. 823.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !