Netilmicin

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)

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.

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

  1. ^ "Drug and medical device highlights 2019: Helping you maintain and improve your health". Health Canada. 18 November 2020. Retrieved 28 March 2024.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 508. ISBN 9783527607495.
  3. ^ "Netilmicin". SPS - Specialist Pharmacy Service. 2 June 2020. Retrieved 21 August 2020.
  4. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

Further reading

  • Wright J (1976). "Synthesis of 1-N-ethylsisomicin: a broad-spectrum semisynthetic aminoglycoside antibiotic". Journal of the Chemical Society, Chemical Communications (6): 206–208. doi:10.1039/C39760000206.
  • Hemsworth S, Nunn A, Selwood K, Osborne C, Jones A, Pizer B (2005). "Once-daily netilmicin for neutropenic pyrexia in paediatric oncology". Acta Paediatr. 94 (3): 268–74. doi:10.1080/08035250510025923. PMID 16028643.
  • Klingenberg C, Småbrekke L, Lier T, Flaegstad T (2004). "Validation of a simplified netilmicin dosage regimen in infants". Scand J Infect Dis. 36 (6–7): 474–9. doi:10.1080/00365540410020613. PMID 15307571. S2CID 29092705.
  • Brooks J, Marlow N, Reeves B, Millar M (2004). "Use of once-daily netilmicin to treat infants with suspected sepsis in a neonatal intensive care unit". Biol Neonate. 86 (3): 170–5. doi:10.1159/000079423. PMID 15237240. S2CID 37410607.