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Revision as of 13:48, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456705714 of page Netilmicin for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').  Latest revision as of 15:04, 14 November 2024 edit Marbletan (talk | contribs)Extended confirmed users5,350 editsNo edit summary 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 400324840 | verifiedrevid = 462259703
| IUPAC_name = (2''R'',3''R'',4''R'',5''R'')-​2-​{oxy}-​6-​(ethylamino)-​2-​hydroxycyclohexyl]oxy}-​5-​methyl-​4-​(methylamino)oxane-​3,5-diol | IUPAC_name = (2''R'',3''R'',4''R'',5''R'')-2-{oxy}-6-(ethylamino)-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
| image = Netilmicin structure.svg | image = Netilmicin structure.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Netromycin
| Drugs.com = {{drugs.com|monograph|streptomycin-sulfate}} | Drugs.com = {{drugs.com|monograph|streptomycin-sulfate}}
| MedlinePlus = a605011 | MedlinePlus = a605011
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| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
⚫ | routes_of_administration = ]
⚫ | ATC_prefix = J01
⚫ | ATC_suffix = GB07
⚫ | ATC_supplemental = {{ATC|S01|AA23}}

| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_CA = Rx-only
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_CA_comment = <ref>{{cite web | title=Drug and medical device highlights 2019: Helping you maintain and improve your health | website=] | 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}}</ref>
| legal_UK = POM
| legal_US = <!-- OTC / Rx-only --> | legal_US = <!-- OTC / Rx-only -->
| legal_status = | legal_status =
⚫ | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = 2.5 hours | elimination_half-life = 2.5 hours
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| synonyms = 1-''N''-Ethylsisomicin
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 56391-56-1 | CAS_number = 56391-56-1
⚫ | ATC_prefix = J01
⚫ | ATC_suffix = GB07
⚫ | ATC_supplemental = {{ATC|S01|AA23}}
| PubChem = 41859 | PubChem = 41859
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00955 | DrugBank = DB00955
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 38195 | ChemSpiderID = 38195
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4O5J85GJJB | UNII = 4O5J85GJJB
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08268 | KEGG = D08268
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1572 --> | ChEMBL = 1572

<!--Chemical data-->
| C=21 | H=41 | N=5 | O=7 | C=21 | H=41 | N=5 | O=7
| molecular_weight = 475.58 g/mol
| smiles = O3(C)(NC)(O)(O2(NCC)C(N)(OC1O\C(=C/CC1N)CN)2O)OC3 | smiles = O3(C)(NC)(O)(O2(NCC)C(N)(OC1O\C(=C/CC1N)CN)2O)OC3
| InChI = 1/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
| InChIKey = CIDUJQMULVCIBT-KALHTFJLBI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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
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| StdInChIKey = CIDUJQMULVCIBT-KALHTFJLSA-N | StdInChIKey = CIDUJQMULVCIBT-KALHTFJLSA-N
}} }}
'''Netilmicin''' ('''1-''N''-ethylsisomicin''') is a semisynthetic ] ], and a derivative of ], produced by '']''. Aminoglycoside antibiotics have the ability to kill a wide variety of ]. Netilmicin is not absorbed from the ] and is therefore only given by injection or infusion. It is only used in the treatment of serious ]s particularly those resistant to ].

<!-- Society and culture -->
It was patented in 1973 and approved for medical use in 1981.<ref name=Fis2006>{{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}}</ref> It was approved for medical use in the UK in December 2019, for the treatment of external infections of the eye.<ref>{{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}}</ref> It is on the ].<ref name="WHO22nd">{{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 }}</ref>
__TOC__

== Comparison with drugs ==
According to the ] (BNF), netilmicin has similar activity to gentamicin, but less ] in those needing treatment for longer than 10 days. Netilmicin is active against a number of gentamicin-resistant ] but is less active against '']'' than gentamicin or ].{{cn|date=March 2023}}

==References==
{{Reflist}}

== Further reading ==
{{refbegin}}
* {{cite journal |vauthors=Wright J | title = Synthesis of 1-N-ethylsisomicin: a broad-spectrum semisynthetic aminoglycoside antibiotic. | journal = Journal of the Chemical Society, Chemical Communications | issue = 6 | pages = 206–208 | year = 1976 | doi = 10.1039/C39760000206}}
* {{cite journal |vauthors=Hemsworth S, Nunn A, Selwood K, Osborne C, Jones A, Pizer B | title = Once-daily netilmicin for neutropenic pyrexia in paediatric oncology. | journal = Acta Paediatr | volume = 94 | issue = 3 | pages = 268–74 | year = 2005 | pmid = 16028643 | doi = 10.1080/08035250510025923}}
* {{cite journal |vauthors=Klingenberg C, Småbrekke L, Lier T, Flaegstad T | title = Validation of a simplified netilmicin dosage regimen in infants. | journal = Scand J Infect Dis | volume = 36 | issue = 6–7 | pages = 474–9 | year = 2004 | pmid = 15307571 | doi = 10.1080/00365540410020613| s2cid = 29092705 }}
* {{cite journal |vauthors=Brooks J, Marlow N, Reeves B, Millar M | title = Use of once-daily netilmicin to treat infants with suspected sepsis in a neonatal intensive care unit. | journal = Biol Neonate | volume = 86 | issue = 3 | pages = 170–5 | year = 2004 | pmid = 15237240 | doi = 10.1159/000079423| s2cid = 37410607 }}
{{refend}}

{{Protein synthesis inhibitor antibiotics}}
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