Netilmicin

Chemical compound From Wikipedia, the free encyclopedia

Netilmicin (1-N-ethylsisomicin) is a semisynthetic aminoglycoside antibiotic, and a derivative of sisomicin, produced by Micromonospora inyoensis. Aminoglycoside antibiotics have the ability to kill a wide variety of bacteria. Netilmicin is not absorbed from the gut and is therefore only given by injection or infusion. It is only used in the treatment of serious infections particularly those resistant to gentamicin.

Trade namesNetromycin
Other names1-N-Ethylsisomicin
AHFS/Drugs.comMonograph
MedlinePlusa605011
Quick facts Clinical data, Trade names ...
Netilmicin
Clinical data
Trade namesNetromycin
Other names1-N-Ethylsisomicin
AHFS/Drugs.comMonograph
MedlinePlusa605011
Routes of
administration		Topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~0%
Elimination half-life2.5 hours
Identifiers
  • (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4-Amino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.054.661 Edit this at Wikidata
Chemical and physical data
FormulaC21H41N5O7
Molar mass475.587 g·mol−1
3D model (JSmol)
  • O[C@]3(C)[C@H](NC)[C@@H](O)[C@@H](O[C@H]2[C@H](NCC)C[C@H](N)[C@@H](OC1O\C(=C/CC1N)CN)[C@@H]2O)OC3
  • InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11?,12-,13+,14-,15+,16+,17-,18+,19?,20+,21-/m0/s1 checkY
  • Key:CIDUJQMULVCIBT-KALHTFJLSA-N checkY
 ☒NcheckY (what is this?)  (verify)
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It was patented in 1973 and approved for medical use in 1981.[2] It was approved for medical use in the UK in December 2019, for the treatment of external infections of the eye.[3] It is on the World Health Organization's List of Essential Medicines.[4]

Comparison with drugs

According to the British National Formulary (BNF), netilmicin has similar activity to gentamicin, but less ototoxicity in those needing treatment for longer than 10 days. Netilmicin is active against a number of gentamicin-resistant Gram-negative bacteria but is less active against Pseudomonas aeruginosa than gentamicin or tobramycin.[citation needed]

References

Further reading

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