Netilmicin

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.

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
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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]}