Netilmicin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 462259703

| 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

| image = Netilmicin structure.svg

| tradename = Netromycin

| Drugs.com = {{drugs.com|monograph|streptomycin-sulfate}}

| MedlinePlus = a605011

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| routes_of_administration = Topical

| ATC_prefix = J01

| ATC_suffix = GB07

| ATC_supplemental = {{ATC|S01|AA23}}

| legal_AU =

| legal_CA = Rx-only

| legal_CA_comment = {{cite web | title=Drug and medical device highlights 2019: Helping you maintain and improve your health | website=Health Canada | date=18 November 2020 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/drug-medical-device-highlights-2019.html | access-date=28 March 2024}}

| legal_UK = POM

| legal_US =

| legal_status =

| bioavailability = ~0%

| protein_bound =

| metabolism =

| elimination_half-life = 2.5 hours

| excretion =

| synonyms = 1-N-Ethylsisomicin

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 56391-56-1

| PubChem = 41859

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00955

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 38195

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4O5J85GJJB

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08268

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1572

| C=21 | H=41 | N=5 | O=7

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CIDUJQMULVCIBT-KALHTFJLSA-N

}}

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.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=508 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA508 |language=en}} It was approved for medical use in the UK in December 2019, for the treatment of external infections of the eye.{{cite web | title=Netilmicin | website=SPS - Specialist Pharmacy Service | date=2 June 2020 | url=https://www.sps.nhs.uk/medicines/netilmicin/ | access-date=21 August 2020}} It is on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}

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