Editing Gentamicin (section)

{{Short description|Antibiotic medication}}
{{Use dmy dates|date=September 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443833957
| image = Gentamicin skeletal formula labelled.svg
| image_class = skin-invert-image
| alt = 
| image2 = Gentamicin C1 ball-and-stick model from xtal 2016.png
| alt2 = 

<!--Clinical data-->
| pronounce = {{IPAc-en|ˌ|dʒ|ɛ|n|t|ə|ˈ|m|aɪ|s|ə|n}}
| tradename = Cidomycin, Genticyn, Garamycin, others
| Drugs.com = {{drugs.com|monograph|gentamicin-sulfate}}
| MedlinePlus = a682275
| DailyMedID = Gentamicin
| pregnancy_AU      = D
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Gentamicin Use During Pregnancy | website=Drugs.com | date=28 February 2019 | url=https://www.drugs.com/pregnancy/gentamicin.html | access-date=11 February 2020}}</ref>
| routes_of_administration = [[Intravenous therapy|Intravenous]], [[Ophthalmic drug administration|eye drop]], [[Intramuscular injection]], [[Topical administration]], [[ear drop]]
| class        = [[Aminoglycoside antibiotic]]
| ATC_prefix = D06
| ATC_suffix = AX07
| ATC_supplemental =  {{ATC|J01|GB03}} {{ATC|S01|AA11}} {{ATC|S02|AA14}} {{ATC|S03|AA06}} {{ATCvet|A07|AA91}} {{ATCvet|G01|AA91}} {{ATCvet|G51|AA04}} {{ATCvet|J51|GB03}}

<!-- Legal status -->
| legal_AU          = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment  = 
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment  = 
| legal_CA          = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment  = 
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  = 
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  = 
| legal_UK          = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment  = 
| legal_US          = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US_comment  = 
| legal_EU = Rx-only
| legal_EU_comment = <ref>{{cite web |title = Active substance: gentamicin (systemic use) | url = https://www.ema.europa.eu/documents/psusa/gentamicin-list-nationally-authorised-medicinal-products-psusa/00009159/202003_en.pdf | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = 26 November 2020 }}</ref>
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  = 
| legal_status = Rx only

<!-- Pharmacokinetic data -->
| bioavailability = limited bioavailability by mouth
| protein_bound = 0–10%
| elimination_half-life = 2 h
| excretion = Kidney

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1403-66-3
| PubChem = 3467
| IUPHAR_ligand = 2427
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00798
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390067
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = T6Z9V48IKG
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08013
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27412
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 195892

<!--Chemical data-->
| IUPAC_name = (3''R'',4''R'',5''R'')-2-<nowiki/>{[(1''S'',2''S'',3''R'',4''S'',6''R'')-4,6-<br />diamino-3-<nowiki/>{[(2''R'',3''R'',6''S'')-<br />3-amino-6-[(1''R'')-<br />1-(methylamino)ethyl]oxan-2-yl]oxy}-<br />2-hydroxycyclohexyl]oxy}-5-methyl-<br />4-(methylamino)oxane-3,5-diol
| C=21 | H=43 | N=5 | O=7
| smiles = O[C@]3(C)[C@H](NC)[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]1O[C@H](C(NC)C)CC[C@H]1N)[C@@H]2O)OC3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CEAZRRDELHUEMR-URQXQFDESA-N
}}
{{Chembox
|container_only = yes
| Section3       = {{Chembox Hazards
| Hazards_ref = <ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/Gentamicin#section=GHS-Classification|title=Gentamicin|website=PubChem|publisher=National Library of Medicine|access-date=November 20, 2024}}</ref>
| GHSPictograms = {{GHS08|Health Hazard}}{{GHS07|Irritant}}{{GHS09|Environmental Hazard}}
| HPhrases = {{H-phrases|317|334|360|360D|372|410}}
| PPhrases = {{P-phrases|203|233|260|264|270|271|272|273|280|284|302|352|304|340|318|319|321|333|317|342|316|362|364|391|403|405|501}}
  }}
}}
<!-- Definition and uses -->
'''Gentamicin''' is an [[aminoglycoside]] [[antibiotic]] used to treat several types of [[bacterial infection]]s.<ref name=AHFS2015>{{cite web|title = Gentamicin sulfate|url = https://www.drugs.com/monograph/gentamicin-sulfate.html|publisher = The American Society of Health-System Pharmacists|access-date = 15 August 2015|url-status = live|archive-url = https://web.archive.org/web/20150816010048/http://www.drugs.com/monograph/gentamicin-sulfate.html|archive-date = 16 August 2015}}</ref> This may include [[osteomyelitis|bone infections]], [[endocarditis]], [[pelvic inflammatory disease]], [[meningitis]], [[pneumonia]], [[urinary tract infections]], and [[sepsis]] among others.<ref name=AHFS2015/> It is not effective for [[gonorrhea]] or [[chlamydia infection]]s.<ref name=AHFS2015/> It can be given [[Intravenous therapy|intravenously]], by [[intramuscular injection]], or [[topical]]ly.<ref name=AHFS2015/> Topical formulations may be used in burns or for infections of the outside of the eye.<ref>{{cite book| vauthors = Bartlett J |title=Clinical Ocular Pharmacology|date=2013|publisher=Elsevier|isbn=9781483193915|page=214|edition=s|url=https://books.google.com/books?id=kA8lBQAAQBAJ&pg=PA214|url-status=live|archive-url=https://web.archive.org/web/20151222132453/https://books.google.ca/books?id=kA8lBQAAQBAJ&pg=PA214|archive-date=22 December 2015}}</ref> It is often only used for two days until [[bacterial culture]]s determine what specific antibiotics the infection is sensitive to.<ref name="ap01">{{cite journal | vauthors = Moulds R, Jeyasingham M |journal=Australian Prescriber |title=Gentamicin: a great way to start |date=October 2010 |volume=33 |issue=5 |pages=134–135 |doi=10.18773/austprescr.2010.062 |doi-access=free }}</ref> The dose required should be monitored by blood testing.<ref name=AHFS2015/>

<!-- Side effects and mechanism -->
Gentamicin can cause [[ototoxic|inner ear problems]] and [[nephrotoxic|kidney problems]].<ref name=AHFS2015/> The inner ear problems can include problems with balance and [[hearing loss]].<ref name=AHFS2015/> These problems may be permanent.<ref name=AHFS2015/> If used during [[pregnancy]], it can cause harm to the developing fetus.<ref name=AHFS2015/> However, it appears to be safe for use during [[breastfeeding]].<ref name=GenB>{{cite web|title=Gentamicin use while breastfeeding|url=https://www.drugs.com/breastfeeding/gentamicin.html|access-date=15 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150906222610/http://www.drugs.com/breastfeeding/gentamicin.html|archive-date=6 September 2015}}</ref> Gentamicin is a type of aminoglycoside <ref name=AHFS2015/> and works by disrupting the ability of the bacteria to make proteins, which typically [[bactericidal|kills the bacteria]].<ref name=AHFS2015/>

<!-- Society and culture -->
Gentamicin is naturally produced by the bacterium ''[[Micromonospora purpurea]]'',<ref name="pmid14184912">{{cite journal | vauthors = Weinstein MJ, Luedemann GM, Oden EM, Wagman GH, Rosselet JP, Marquez JA, Coniglio CT, Charney W, Herzog HL, Black J | title = Gentamicin, a new antibiotic complex from Micromonospora | journal = Journal of Medicinal Chemistry | volume = 6 | issue = 4 | pages = 463–464 | date = July 1963 | pmid = 14184912 | doi = 10.1021/jm00340a034 }}</ref><ref name=AHFS2015/> was patented in 1962, approved for medical use in 1964.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR  |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=507 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA507 }}</ref> The antibiotic is collected from the culture of the ''[[Micromonospora]]'' by perforating the cell wall of the bacterium. Current research is underway to understand the [[biosynthesis]] of this antibiotic in an attempt to increase expression and force secretion of gentamicin for higher [[titer]]. Gentamicin is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> The World Health Organization classifies gentamicin as critically important for human medicine.<ref>{{cite book | vauthors=((World Health Organization)) | year=2019 | title=Critically important antimicrobials for human medicine | edition=6th revision |  author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl=10665/312266 | id=License: CC BY-NC-SA 3.0 IGO | isbn=9789241515528 | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref>{{cite book| vauthors = Burchum J |title=Lehne's pharmacology for nursing care|date=2014|publisher=Elsevier Health Sciences|isbn=9780323340267|page=1051|url=https://books.google.com/books?id=C7_NBQAAQBAJ&pg=PA1052|url-status=live|archive-url=https://web.archive.org/web/20160311015121/https://books.google.ca/books?id=C7_NBQAAQBAJ&pg=PA1052|archive-date=11 March 2016}}</ref>