Netilmicin

Netilmicin

Clinical data
Trade names	Netromycin
Other names	1-N-Ethylsisomicin
AHFS/Drugs.com	Monograph
MedlinePlus	a605011
Routes of administration	Topical
ATC code	J01GB07 ( WHO ) S01AA23 ( WHO )
Legal status
Legal status	CA: ℞-only [1] UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	~0%
Elimination half-life	2.5 hours
Identifiers
IUPAC name (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	56391-56-1  Y
PubChem CID	41859
DrugBank	DB00955  Y
ChemSpider	38195  Y
UNII	4O5J85GJJB
KEGG	D08268  Y
ChEMBL	ChEMBL1572  N
CompTox Dashboard (EPA)	DTXSID1048542
ECHA InfoCard	100.054.661
Chemical and physical data
Formula	C21H41N5O7
Molar mass	475.587 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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 Y Key:CIDUJQMULVCIBT-KALHTFJLSA-N Y
NY  (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. Archived from the original on 24 October 2021. 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.