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Revision as of 08:22, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 05:44, 23 January 2025 edit undoDMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators187,055 edits subsumed rule
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			{{Short description|Antibiotic medication}}
			{{Use dmy dates|date=September 2024}}
			{{cs1 config|name-list-style=vanc|display-authors=6}}
	{{Drugbox		{{Drugbox
			| Verifiedfields = changed
	| verifiedrevid = 407832838
			| verifiedrevid = 443833957
	| IUPAC_name = (3''R'',4''R'',5''R'')-2-{oxan-2-yl]oxy}-<br />2-hydroxycyclohexyl]oxy}-5-methyl-<br />4-(methylamino)oxane-3,5-diol
	| image = Gentamicin C2.svg		| image = Gentamicin C2.svg
			| image_class = skin-invert-image
	| width = 350
			| alt =
	| image2 = Gentamicin.png		| image2 = Gentamicin.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 = ], ], ], ], ]
			| class = ]
			| 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_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 390067		| ChemSpiderID = 390067
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = T6Z9V48IKG		| UNII = T6Z9V48IKG
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| InChI = 1/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
			| KEGG = D08013
	| InChIKey = CEAZRRDELHUEMR-URQXQFDEBJ
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| smiles = O3(C)(NC)(O)(O2(N)C(N)(O1O(C(NC)C)CC1N)2O)OC3
			| ChEBI = 27412
	| CASNo_Ref = {{cascite|correct|CAS}}
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 195892		| ChEMBL = 195892
			<!--Chemical data-->
			| IUPAC_name = (3''R'',4''R'',5''R'')-2-<nowiki/>{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 = O3(C)(NC)(O)(O2(N)C(N)(O1O(C(NC)C)CC1N)2O)OC3
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| 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		| 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_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = CEAZRRDELHUEMR-URQXQFDESA-N		| StdInChIKey = CEAZRRDELHUEMR-URQXQFDESA-N
	| CAS_number = 1403-66-3
	| 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}}
	| ChEBI = 27412
	| PubChem = 3467
	| IUPHAR_ligand = 2427
	| DrugBank = APRD00214
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D08013
	| C=21 | H=43 | N=5 | O=7
	| molecular_weight = 477.596 g/mol
	| bioavailability = limited oral bioavailability
	| protein_bound = 0-10%
	| metabolism =
	| elimination_half-life = 2 hrs
	| excretion = renal
	| pregnancy_category = D
	| legal_status =
	| routes_of_administration = ], ], ]
	}}		}}
			{{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 ] ] used to treat several types of ]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 ], ], ], ], ], ], and ] among others.<ref name=AHFS2015/> It is not effective for ] or ]s.<ref name=AHFS2015/> It can be given ], by ], or ]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 ]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''' is an ] ], used to treat many types of ]l infections, particularly those caused by ] organisms.<ref name="ap01">{{cite journal |author=Moulds, Robert and Jeyasingham, Melanie |journal=Australian Prescriber |title=Gentamicin: a great way to start |year=2010 |month=October |issue=33 |pages=134–135 |url=http://www.australianprescriber.com/magazine/33/5/134/5}}</ref> However, gentamicin is not used for '']'', '']'' or '']''. Gentamicin is also ] and ], with this toxicity remaining a major problem in clinical use.<ref name="ap01" />
			Gentamicin can cause ] and ].<ref name=AHFS2015/> The inner ear problems can include problems with balance and ].<ref name=AHFS2015/> These problems may be permanent.<ref name=AHFS2015/> If used during ], it can cause harm to the developing fetus.<ref name=AHFS2015/> However, it appears to be safe for use during ].<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 ].<ref name=AHFS2015/>
			<!-- Society and culture -->
	It is synthesized by '']'', a genus of ] widely present in the environment (water and soil). To highlight their specific biological origins, gentamicin and other related antibiotics produced by this genus (], ], ], ], ]) generally have their spellings ending in ''~micin'' and not in ''~mycin''. Gentamicin is a ] antibiotic that works by binding the ] subunit of the bacterial ], interrupting protein synthesis.
			Gentamicin is naturally produced by the bacterium '']'',<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 '']'' by perforating the cell wall of the bacterium. Current research is underway to understand the ] of this antibiotic in an attempt to increase expression and force secretion of gentamicin for higher ]. Gentamicin is on the ].<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 ].<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>
			==Medical uses==
	Like all aminoglycosides, when gentamicin is given orally, it is not systemically active. This is because it is not absorbed to any appreciable extent from the ]. It is administered ], ] or ]ly to treat infections. It appears to be completely eliminated unchanged in the urine. Urine must be collected for many days to recover all of a given dose because the drug binds avidly to certain tissues.
			Gentamicin is active against a wide range of bacterial infections, mostly Gram-negative bacteria including '']'', '']'', '']'', '']'', ''Enterobacter aerogenes'', '']'', and the Gram-positive '']''.<ref name="Baxter Corporation">{{Cite web|url = http://www.baxter.ca/en/downloads/product_information/GENTAMICIN(E)_PM_AUG282012_EN.pdf|title = Gentamicin|access-date = 2 November 2015|publisher = Baxter Corporation|url-status = dead|archive-url = https://web.archive.org/web/20160304124731/http://www.baxter.ca/en/downloads/product_information/GENTAMICIN(E)_PM_AUG282012_EN.pdf|archive-date = 4 March 2016}}</ref> Gentamicin is used in the treatment of respiratory tract infections, urinary tract infections, blood, bone and soft tissue infections of these susceptible bacteria.<ref name="Product Monograph">{{Cite web|url = http://www.sandoz.ca/cs/groups/public/@sge_ca/documents/document/n_prod_1301121.pdf|title = Gentamicin Injection USP | work = Product Monograph|access-date = 2 November 2015|publisher = Sandoz Canada Inc|url-status = dead|archive-url = https://web.archive.org/web/20150412102019/http://www.sandoz.ca/cs/groups/public/%40sge_ca/documents/document/n_prod_1301121.pdf|archive-date = 12 April 2015}}</ref>
			There is insufficient evidence to support gentamicin as the first line treatment of '']'' infection.<ref>{{cite journal | vauthors = Hathorn E, Dhasmana D, Duley L, Ross JD | title = The effectiveness of gentamicin in the treatment of Neisseria gonorrhoeae: a systematic review | journal = Systematic Reviews | volume = 3 | pages = 104 | date = September 2014 | pmid = 25239090 | pmc = 4188483 | doi = 10.1186/2046-4053-3-104 | doi-access = free }}</ref> Gentamicin is not used for '']'' or '']'' bacterial infections (because of the risk of the person going into shock from lipid A ] found in certain Gram-negative organisms). Gentamicin is also useful against '']'' (responsible for ]), its relatives, and '']'' (the organism responsible for ] often seen in hunters and trappers).<ref>{{cite book| vauthors = Goljan EF |title = Rapid Review Pathology|edition = 3rd|year = 2011|publisher = Elsevier|location = Philadelphia, Pennsylvania|isbn = 978-0-323-08438-3|pages = 241}}</ref>
	'']'' has shown some resistance to gentamicin, despite being Gram-negative. Reluctance to use gentamicin for empirical therapy has led to increased use of alternative broad-spectrum antibiotics, which some experts suggest has led to the prevalence of antibiotic-resistant bacterial infections by ] and other so-called "superbugs".<ref name="ap01" />
			Some '']'', ''] spp.'', ''] spp.'', '']'' and other ''Staphylococcus spp.'' have varying degrees of ] to gentamicin.<ref>{{cite web|title = Gentamicin spectrum of bacterial susceptibility and Resistance|url = http://www.toku-e.com/Upload/Products/PDS/20120604005203.pdf | publisher = TOKU-E |access-date = 15 May 2012|url-status = dead|archive-url = https://web.archive.org/web/20150220033338/http://www.toku-e.com/Upload/Products/PDS/20120604005203.pdf|archive-date = 20 February 2015}}</ref>
	Gentamicin is one of the few heat-stable antibiotics that remain active even after ], which makes it particularly useful in the preparation of some microbiological growth media. It is used during orthopaedic surgery when high temperatures are required for the setting of cements (e.g. hip replacements).<ref>{{cite journal | doi=10.1016/S0142-9612(03)00554-4 | author=Hendriks JGE, van Horn JR, van der Mei HC, and Busscher, HJ| title=Backgrounds of antibiotic-loaded bone cement and prosthesis-related infection| journal=Biomaterials | year=2004 | volume=25 | issue=3 | pages=545–556 | pmid=14585704}}</ref>
			===Special populations===
			====Pregnancy and breastfeeding====
			Gentamicin is not recommended in pregnancy unless the benefits outweigh the risks for the mother. Gentamicin can cross the ] and several reports of ] in children have been seen. ] injection of gentamicin in mothers can cause ] in the ].<ref name="Product Monograph" />
			The safety and efficacy for gentamicin in nursing mothers has not been established. Detectable gentamicin levels are found in human breast milk and in nursing babies.<ref name="Product Monograph" />
	==Spectrum of activity==
	Active against a wide range of human bacterial infections, mostly Gram-negative bacteria including '']'', '']'', '']'', and the Gram-positive '']''.<ref></ref> Gentamicin is not used for '']'', '']'' or '']'' bacterial infections (because of the risk of the patient going into shock from lipid A ] found in certain Gram-negative organisms). Gentamicin is also useful against '']'' and its relatives.
	==Side effects==		====Elderly====
			In the elderly, ] should be assessed before beginning therapy as well as during treatment due to a decline in glomerular filtration rate. Gentamicin levels in the body can remain higher for a longer period of time in this population. Gentamicin should be used cautiously in persons with ], ], ], or ] dysfunction.<ref name="Baxter Corporation" />
	These aminoglycosides are toxic to the sensory cells of the ear, but they vary greatly in their relative effects on hearing versus balance. Gentamicin is a vestibulotoxin, and can cause permanent loss of ], caused by damage to the vestibular apparatus of the inner ear, usually if taken at high doses or for prolonged periods of time, but there are well documented cases in which gentamicin completely destroyed the vestibular apparatus after three to five days.{{Citation needed|date=May 2010}} A small number of affected individuals have a normally harmless mutation in their mitochondrial RNA (m1555 A>G), that allows the gentamicin to affect their cells. The cells of the ] are particularly sensitive to this, sometimes causing complete hearing loss.<ref> at the American Hearing Research Foundation</ref> However, gentamicin is sometimes used intentionally for this purpose in severe ], to disable the ].
			====Children====
	Gentamicin can also be highly ], particularly if multiple doses accumulate over a course of treatment. For this reason gentamicin is usually dosed by ]. Various formulae exist for calculating gentamicin dosage. Also trough and peak serum levels of gentamicin are monitored during treatment, generally before and after the third dose is infused.
			Gentamicin may not be appropriate to use in children, including babies. Studies have shown higher ] levels and a longer ] in this population.<ref>{{cite journal | vauthors = Sato Y | title = Pharmacokinetics of antibiotics in neonates | journal = Acta Paediatrica Japonica | volume = 39 | issue = 1 | pages = 124–131 | date = February 1997 | pmid = 9124044 | doi = 10.1111/j.1442-200X.1997.tb03569.x | s2cid = 23564581 }}</ref> ] should be checked periodically during therapy. Long-term effects of treatment can include hearing loss and balance problems. ], ], and ] have been reported when used by injection.<ref name="Baxter Corporation" />
			==Contraindications==
	Gentamicin, like other ], causes ] by inhibiting protein synthesis in renal cells. This mechanism specifically causes necrosis of cells in the ], resulting in ] which can lead to ].<ref>Sundin DP, Sandoval R, Molitoris BA: Gentamicin Inhibits Renal Protein and Phospholipid Metabolism in Rats: Implications Involving Intracellular Trafficking. J Am Soc Nephrol 12:114-123, 2001</ref>
			Gentamicin should not be used if a person has a history of ], such as ], or other serious toxic reaction to gentamicin or any other ].<ref name="Product Monograph" /> Greater care is required in people with ] and other neuromuscular disorders as there is a risk of worsening weakness.<ref name=AHFS2015/> Gentamicin should also be avoided when prescribing empirical antibiotics in the setting of possible infant botulism (Ampicillin with Gentamicin is commonly used as empiric therapy in infants) also due to worsening of neuromuscular function.<ref>{{cite journal | vauthors = Santos JI, Swensen P, Glasgow LA | title = Potentiation of Clostridium botulinum toxin aminoglycoside antibiotics: clinical and laboratory observations | journal = Pediatrics | volume = 68 | issue = 1 | pages = 50–54 | date = July 1981 | doi = 10.1542/peds.68.1.50 | pmid = 7243509 | s2cid = 36001577 | url = https://pubmed.ncbi.nlm.nih.gov/7243509/ }}</ref>
			==Adverse effects==
	Side effects of gentamicin toxicity vary from patient to patient. Side effects may become apparent shortly after or up to months after gentamicin is administered. Symptoms of gentamicin toxicity include:
			Adverse effects of gentamicin can range from less severe reactions, such as nausea and vomiting, to more severe reactions including:<ref name="Baxter Corporation" />
	*Balance difficulty
			* Low blood cell counts
	*Bouncing, unsteady vision
			* ]
	*Ringing in the ears (])
			* ] problems
	*Difficulty multi-tasking, particularly when standing
			* ] (neuropathy)
			* ] (nephrotoxicity)
			* ] (ototoxicity)
			] and ] are thought to be dose related with higher doses causing greater chance of toxicity.<ref name="Baxter Corporation" /> These two toxicities may have delayed presentation, sometimes not appearing until after completing treatment.<ref name="Baxter Corporation" />
			===Kidney damage===
	Psychiatric symptoms related to gentamicin can occur. These include anorexia, confusion, depression, disorientation and visual hallucinations.<ref>AJ Giannini, HR Black. Psychiatric, Psychogenic and Somatopsychic Disorders Handbook. Garden City, NY. Medical Examination Publishing Co.,1978. Pp.136-137. ISBN 0-87488-596-5.</ref>
			] is a problem in 10–25% of people who receive aminoglycosides, and gentamicin is one of the most nephrotoxic drugs of this class.<ref name="Lopez-Novoa_2011" /> Oftentimes, acute nephrotoxicity is reversible, but it may be fatal.<ref name="Baxter Corporation" /> The risk of nephrotoxicity can be affected by the dose, frequency, duration of therapy, and concurrent use of certain medications, such as ], ], ], ], ], ], ], and ].<ref name="Lopez-Novoa_2011" />
	Immediate professional help should be sought if any of these symptoms or others appear after administration of aminoglycosides. General medical practitioners should refer patients with such symptoms to an ], commonly known as an 'ear, nose, and throat doctor', for comprehensive tests.
			Factors that increase risk of nephrotoxicity include:<ref name="Lopez-Novoa_2011" />
	A number of factors and determinants should be taken into account when using gentamicin, including differentiation between empirical and directed therapy which will affect dosage and treatment period.<ref name="ap01" /> Many medical practitioners freely administer gentamicin as an antibiotic without advising patients of the severe and permanent potential ramifications of its use. Gentamicin is well known to be a cheap, low cost yet old medicine as compared to modern alternatives, and is typically US$3–6 per dosage less than modern alternatives.
			* Increased age
			* Reduced ]
			* Pregnancy
			* ]
			* Hepatic dysfunction
			* Volume depletion
			* ]
			* Sodium depletion
			Kidney dysfunction is monitored by measuring ] in the blood, electrolyte levels, ], ], and concentrations of other chemicals, such as urea, in the blood.<ref name="Lopez-Novoa_2011">{{cite journal | vauthors = Lopez-Novoa JM, Quiros Y, Vicente L, Morales AI, Lopez-Hernandez FJ | title = New insights into the mechanism of aminoglycoside nephrotoxicity: an integrative point of view | journal = Kidney International | volume = 79 | issue = 1 | pages = 33–45 | date = January 2011 | pmid = 20861826 | doi = 10.1038/ki.2010.337 | doi-access = free }}</ref>
			===Inner ear===
	===Treatment and Recovery from Toxicity===
			About 11% of the population who receives aminoglycosides experience damage to their ].<ref>{{cite journal | vauthors = East JE, Foweraker JE, Murgatroyd FD | title = Gentamicin induced ototoxicity during treatment of enterococcal endocarditis: resolution with substitution by netilmicin | journal = Heart | volume = 91 | issue = 5 | pages = e32 | date = May 2005 | pmid = 15831617 | pmc = 1768868 | doi = 10.1136/hrt.2003.028308 }}</ref> The common symptoms of inner ear damage include ], hearing loss, ], ], and dizziness.<ref name="Selimoglu_2007" /> Chronic use of gentamicin can affect two areas of the ears. First, damage of the inner ear hair cells can result in irreversible hearing loss. Second, damage to the inner ear ] apparatus can lead to balance problems.<ref name="Selimoglu_2007">{{cite journal | vauthors = Selimoglu E | title = Aminoglycoside-induced ototoxicity | journal = Current Pharmaceutical Design | volume = 13 | issue = 1 | pages = 119–126 | date = 1 January 2007 | pmid = 17266591 | doi = 10.2174/138161207779313731 }}</ref> To reduce the risk of ototoxicity during treatment, it is recommended to stay hydrated.<ref name="Baxter Corporation" />
	Many people recover from gentamicin toxicity naturally over time if the drug is discontinued, but they recover slowly and usually incompletely.{{Citation needed|date=April 2009}} Sometimes the toxicity of gentamicin can still increase over months after the last dose. Upon cessation of gentamicin therapy symptoms such as tinnitus and imbalance may become less pronounced. Sensori-neural hearing loss caused by gentamicin toxicity is permanent however.
			Factors that increase the risk of inner ear damage include:<ref name="Baxter Corporation" /><ref name="Product Monograph" />
	==Production and usage in research==
			* Increased age
	Gentamicin is produced by a ] procedure. It was discovered by a Chinese microbiologist, Yue Wang. The majority of the world's gentamicin production takes place in ] and ]; the last European producer is ], part of ] group.
			* ]
			* Kidney dysfunction
			* Liver dysfunction
			* Higher doses
			* Long courses of therapy
			* Also taking strong diuretics (e.g., ])
			==Pharmacology==
	Gentamicin has been used since the early 1980s in ] research. The ] enables researchers to quantify the ability of ]ic bacteria to invade ] cells. It takes advantage of the fact that gentamicin is not able to penetrate eukaryotic cells.
			===Mechanism of action===
			Gentamicin is a ] antibiotic that works by binding the 30S subunit of the bacterial ribosome, negatively impacting ]. The primary mechanism of action is generally accepted to work through ablating the ability of the ribosome to discriminate on proper ] and ] interactions.<ref>{{cite web|url =http://www.drugbank.ca/drugs/DB00798|work = DrugBank | title = Gentamicin|url-status =live|archive-url =https://web.archive.org/web/20131004221814/http://www.drugbank.ca/drugs/DB00798|archive-date =4 October 2013}}</ref> Typically, if an incorrect tRNA pairs with an mRNA ] at the ] of the ribosome, ]s 1492 and 1493 are excluded from the interaction and retract, signaling the ribosome to reject the ]::] complex.<ref>{{cite journal | vauthors = Dao EH, Poitevin F, Sierra RG, Gati C, Rao Y, Ciftci HI, Akşit F, McGurk A, Obrinski T, Mgbam P, Hayes B, De Lichtenberg C, Pardo-Avila F, Corsepius N, Zhang L, Seaberg MH, Hunter MS, Liang M, Koglin JE, Wakatsuki S, Demirci H | title = Structure of the 30S ribosomal decoding complex at ambient temperature | journal = RNA | volume = 24 | issue = 12 | pages = 1667–1676 | date = December 2018 | pmid = 30139800 | pmc = 6239188 | doi = 10.1261/rna.067660.118 }}</ref> However, when gentamicin binds at helix 44 of the ], it forces the adenosines to maintain the position they take when there is a correct, or cognate, match between aa-tRNA and mRNA.<ref>{{cite journal | vauthors = Wilson DN | title = Ribosome-targeting antibiotics and mechanisms of bacterial resistance | journal = Nature Reviews. Microbiology | volume = 12 | issue = 1 | pages = 35–48 | date = January 2014 | pmid = 24336183 | doi = 10.1038/nrmicro3155 | s2cid = 9264620 }}</ref> This leads to the acceptance of incorrect aa-tRNAs, causing the ribosome to synthesize proteins with wrong ]s placed throughout (roughly every 1 in 500).<ref>{{cite book | vauthors = Garrett R, Douthwaite S, Liljas A, Matheson A, Moore P, Harry N |title=The Ribosome |date=2000 |publisher=ASM Press |isbn=978-1-55581-184-6 |pages=419–429 }}</ref> The non-functional, mistranslated proteins misfold and aggregate, eventually leading to death of the bacterium. Moreover, it has been observed that gentamicin can cause a substantial slowdown in the overall elongation rate of peptide chains in live bacterial cells, independent of the misincorporation of amino acids.<ref>{{cite journal | vauthors = Aguirre Rivera J, Larsson J, Volkov IL, Seefeldt AC, Sanyal S, Johansson M | title = Real-time measurements of aminoglycoside effects on protein synthesis in live cells | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 118 | issue = 9 | date = March 2021 | pmid = 33619089 | pmc = 7936356 | doi = 10.1073/pnas.2013315118 | bibcode = 2021PNAS..11813315A | doi-access = free }}</ref> This finding indicates that gentamicin not only induces errors in protein synthesis but also broadly hampers the efficiency of the translation process itself. An additional mechanism has been proposed based on crystal structures of gentamicin in a secondary binding site at helix 69 of the ], which interacts with helix 44 and ]. At this secondary site, gentamicin is believed to preclude interactions of the ribosome with ribosome recycling factors, causing the two subunits of the ribosome to stay complexed even after translation completes, creating a pool of inactive ribosomes that can no longer ] and translate new proteins.<ref>{{cite journal | vauthors = Borovinskaya MA, Pai RD, Zhang W, Schuwirth BS, Holton JM, Hirokawa G, Kaji H, Kaji A, Cate JH | title = Structural basis for aminoglycoside inhibition of bacterial ribosome recycling | journal = Nature Structural & Molecular Biology | volume = 14 | issue = 8 | pages = 727–732 | date = August 2007 | pmid = 17660832 | doi = 10.1038/nsmb1271 | s2cid = 31576287 }}</ref>
	==References==		==Chemistry==
			=== Structure ===
			]
			Since gentamicin is derived from the species '']'', the backbone for this ] is the aminocyclitol ].<ref name="Yu">{{cite journal | vauthors = Yu Y, Zhang Q, Deng Z | title = Parallel pathways in the biosynthesis of aminoglycoside antibiotics | journal = F1000Research | volume = 6 | pages = 723 | date = 18 May 2017 | pmid = 28620453 | pmc = 5461906 | doi = 10.12688/f1000research.11104.1 | doi-access = free }}</ref><ref name="Dewick">{{cite book | vauthors = Dewick PM |title=Medicinal natural products : a biosynthetic approach |date=2009 |location=Chichester, West Sussex, United Kingdom | publisher = Wiley |isbn=978-0-470-74167-2 |pages=738–750 |edition=3rd}}</ref> This six carbon ring is substituted at the ] 4 and 6 by the amino sugar molecules cyclic ] and ], respectively.<ref name="Kumar" /><ref name="Yu" /> The gentamicin complex, is differentiated into five major components (C<sub>1</sub>, C<sub>1a</sub>, C<sub>2</sub>, C<sub>2a</sub>, C<sub>2b</sub>) and multiple minor components by substitution at the 6' carbon of the purpurosamine unit indicated in the image to the right by R<sup>1</sup> and R<sup>2</sup>.<ref name="Kumar" /><ref name="Yu" /><ref name="Weinstein" /><ref name="Vydrin">{{cite journal | vauthors = Vydrin AF, Shikhaleev IV, Makhortov VL, Shcherenko NN, Kolchanova NV |title=Component Composition of Gentamicin Sulfate Preparations|journal=Pharmaceutical Chemistry Journal |date=2003 |volume=37 |issue=8 |pages=448–450 |doi=10.1023/a:1027372416983|s2cid=43731658 }}</ref> The R<sup>1</sup> and R<sup>2</sup> can have the follow substitutions for some of the species in the gentamicin complex.<ref name="Kumar" /><ref name="Daniels" /><ref name="Dewick" />
			{| class="wikitable"
			|+ Major component
			|-
			! C complex !! R<sup>1</sup> !! R<sup>2</sup>
			|-
			| C<sub>1</sub> || ] group || ] group
			|-
			| C<sub>1a</sub>|| ] || ]
			|-
			| C<sub>2</sub>|| ] || ] group
			|-
			| C<sub>2a</sub> || ] || ] group
			|-
			| C<sub>2b</sub> || ] group || ]
			|}
			Gentamicins consist of three ]: gentosamine/garosamine, 2-deoxystreptamine, and purpurosamine (see illustrations, from left to right).<ref>{{cite journal | vauthors = Benveniste R, Davies J | title = Structure-activity relationships among the aminoglycoside antibiotics: role of hydroxyl and amino groups | journal = Antimicrobial Agents and Chemotherapy | volume = 4 | issue = 4 | pages = 402–409 | date = October 1973 | pmid = 4598613 | pmc = 444567 | doi = 10.1128/AAC.4.4.402 }}</ref><ref>{{cite journal | vauthors = Vastola AP, Altschaefl J, Harford S | title = 5-epi-Sisomicin and 5-epi-Gentamicin B: substrates for aminoglycoside-modifying enzymes that retain activity against aminoglycoside-resistant bacteria | journal = Antimicrobial Agents and Chemotherapy | volume = 17 | issue = 5 | pages = 798–802 | date = May 1980 | pmid = 6967296 | pmc = 283878 | doi = 10.1128/AAC.17.5.798 }}</ref>
			{| class="wikitable centered"
			! colspan="10" class="hintergrundfarbe6" |Gentamicine
			|-
			!Name
			!Structure
			!]
			!]
			!Sum formula
			!Molar mass
			|-
			|
			* Gentamicin A
			|]
			|13291-74-2
			|{{PubChem|86474}}
			|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
			|468.50 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin A<sub>1</sub>
			|]
			|
			|
			|
			|
			|-
			|
			* Gentamicin A<sub>2</sub>
			|]
			|55715-66-7
			|{{PubChem|86489}}
			|C<sub>17</sub>H<sub>33</sub>N<sub>3</sub>O<sub>11</sub>
			|455.46 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin A<sub>3</sub>
			|]
			|55715-67-8
			|{{PubChem|86490}}
			|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
			|468.50 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin A<sub>4</sub>
			|]
			|
			|
			|
			|
			|-
			|
			* Gentamicin B
			* Betamicin
			|]
			|36889-15-3
			|{{PubChem|37569}}
			|C<sub>19</sub>H<sub>38</sub>N<sub>4</sub>O<sub>10</sub>
			|482.53 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin B<sub>1</sub>
			|]
			|36889-16-4
			|{{PubChem|3034288}}
			|C<sub>20</sub>H<sub>40</sub>N<sub>4</sub>O<sub>10</sub>
			|496.55 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin C<sub>1</sub>
			|]
			|25876-10-2
			|{{PubChem|441305}}
			|C<sub>21</sub>H<sub>43</sub>N<sub>5</sub>O<sub>7</sub>
			|477.59 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin C<sub>1a</sub>
			|]
			|26098-04-4
			|{{PubChem|72396}}
			|C<sub>19</sub>H<sub>39</sub>N<sub>5</sub>O<sub>7</sub>
			|449.54 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin C<sub>2</sub>
			|]
			|25876-11-3
			|{{PubChem|72397}}
			|C<sub>20</sub>H<sub>41</sub>N<sub>5</sub>O<sub>7</sub>
			|463.57 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin C<sub>2a</sub>
			|]
			|59751-72-3
			|
			|C<sub>20</sub>H<sub>41</sub>N<sub>5</sub>O<sub>7</sub>
			|463.57 g·mol<sup>−1</sup>
			|-
			|
			* Gentamicin C<sub>2b</sub>
			* Micronomicin
			|]
			|52093-21-7
			|{{PubChem|107677}}
			|C<sub>20</sub>H<sub>41</sub>N<sub>5</sub>O<sub>7</sub>
			|463.57 g·mol<sup>−1</sup>
			|-
			|}
			] and ] exhibit similar structures. ] is 4,5-dehydrogentamicin-C<sub>1a</sub>.
			===Components===
			Gentamicin is composed of a number of related gentamicin components and fractions which have varying degrees of antimicrobial potency.<ref>{{cite journal | vauthors = Weinstein MJ, Wagman GH, Oden EM, Marquez JA | title = Biological activity of the antibiotic components of the gentamicin complex | journal = Journal of Bacteriology | volume = 94 | issue = 3 | pages = 789–790 | date = September 1967 | pmid = 4962848 | pmc = 251956 | doi = 10.1128/JB.94.3.789-790.1967 }}</ref> The main components of gentamicin include members of the gentamicin C complex: gentamicin C<sub>1</sub>, gentamicin C<sub>1a</sub>, and gentamicin C<sub>2</sub> which compose approximately 80% of gentamicin and have been found to have the highest antibacterial activity. Gentamicin A, B, X, and a few others make up the remaining 20% of gentamicin and have lower antibiotic activity than the gentamicin C complex.<ref name="Vydrin" /> The exact composition of a given sample or lot of gentamicin is not well defined, and the level of gentamicin C components or other components in gentamicin may differ from lot-to-lot depending on the gentamicin manufacturer or manufacturing process. Because of this lot-to-lot variability, it can be difficult to study various properties of gentamicin including pharmacokinetics and microorganism susceptibility if there is an unknown combination of chemically related but different compounds.<ref>{{cite journal | vauthors = Isoherranen N, Lavy E, Soback S | title = Pharmacokinetics of gentamicin C(1), C(1a), and C(2) in beagles after a single intravenous dose | journal = Antimicrobial Agents and Chemotherapy | volume = 44 | issue = 6 | pages = 1443–1447 | date = June 2000 | pmid = 10817690 | pmc = 89894 | doi = 10.1128/aac.44.6.1443-1447.2000 }}</ref>
			===Biosynthesis===
			The complete ] of gentamicin is not entirely elucidated. The genes controlling the biosynthesis of gentamicin are of particular interest due to the difficulty in obtaining the antibiotic after production.<ref name="Vydrin" /><ref name="Weinstein">{{cite journal | vauthors = Weinstein MJ, Wagman GH, Oden EM, Marquez JA | title = Biological activity of the antibiotic components of the gentamicin complex | journal = Journal of Bacteriology | volume = 94 | issue = 3 | pages = 789–790 | date = September 1967 | pmid = 4962848 | pmc = 251956 | doi = 10.1128/jb.94.3.789-790.1967 }}</ref><ref name="Daniels" /><ref name="Wagman" /><ref name="Chu" >{{cite journal | vauthors = Chu J, Zhang S, Zhuang Y, Chen J, Li Y |title=Factors affecting the biosynthesis and secretion of gentamicin |journal=Process Biochemistry |date=December 2002 |volume=38 |issue=5 |pages=815–820 |doi=10.1016/S0032-9592(02)00230-3}}</ref> Since gentamicin is collected at the cell surface and the cell surface must be perforated somehow to obtain the antibiotic.<ref name="Vydrin" /><ref name="Weinstein" /><ref name="Daniels" /><ref name="Wagman" /><ref name="Chu"/> Many propose the amount of gentamicin collected after production could increase if the genes are identified and re-directed to secrete the antibiotic instead of collecting gentamicin at the cell surface.<ref name="Vydrin" /><ref name="Weinstein" /><ref name="Daniels" /><ref name="Wagman" /><ref name="Chu"/> Literature also agrees with the gentamicin biosynthesis pathway starting with D-] being ], ], ] and finally ] with D-] to generate ] inside ''] echinospora''.<ref name="Kumar" /> The addition of D-] leads to the first intermediate of the gentamicin C complex pathway, gentamicin A2.<ref name="Kumar" /><ref name="TestaII" /> Gentamicin A2 is C-methylated and ]ized into gentamicin X<sub>2</sub>, the first branch point of this biosynthesis pathway<ref name="TestaII">{{cite journal | vauthors = Testa RT, Tilley BC | title = Biotransformation, a new approach to aminoglycoside biosynthesis: II. Gentamicin | journal = The Journal of Antibiotics | volume = 29 | issue = 2 | pages = 140–146 | date = February 1976 | pmid = 931800 | doi = 10.7164/antibiotics.29.140 | doi-access = free }}</ref>
			When X<sub>2</sub> is acted on by the ]-dependent ] ] enzyme GenK, the ] 6' is methylated to form the pharmacologically active intermediate G418<ref name="Kim">{{cite journal | vauthors = Kim HJ, McCarty RM, Ogasawara Y, Liu YN, Mansoorabadi SO, LeVieux J, Liu HW | title = GenK-catalyzed C-6' methylation in the biosynthesis of gentamicin: isolation and characterization of a cobalamin-dependent radical SAM enzyme | journal = Journal of the American Chemical Society | volume = 135 | issue = 22 | pages = 8093–8096 | date = June 2013 | pmid = 23679096 | pmc = 3796153 | doi = 10.1021/ja312641f }}</ref><ref name="TestaII" /><ref name="Kumar" /><ref name="Hong">{{cite journal | vauthors = Hong W, Yan L | title = Identification of gntK, a gene required for the methylation of purpurosamine C-6' in gentamicin biosynthesis | journal = The Journal of General and Applied Microbiology | volume = 58 | issue = 5 | pages = 349–356 | date = 2012 | pmid = 23149679 | doi = 10.2323/jgam.58.349 | doi-access = free }}</ref> G418 then undergoes ] and ] at the C6' position by the dehydrogenase gene, GenQ, to generate the pharmacologically active JI-20B, although another intermediate, 6'-dehydro-6'oxo-G418 (6'DOG) is proposed to be in-between this step and for which the gene GenB1 is proposed as the ] gene.<ref name="Kumar" /><ref name="Guo">{{cite journal | vauthors = Guo J, Huang F, Huang C, Duan X, Jian X, Leeper F, Deng Z, Leadlay PF, Sun Y | title = Specificity and promiscuity at the branch point in gentamicin biosynthesis | journal = Chemistry & Biology | volume = 21 | issue = 5 | pages = 608–618 | date = May 2014 | pmid = 24746560 | pmc = 4039129 | doi = 10.1016/j.chembiol.2014.03.005 }}</ref> JI-20B is ] and ]ized to first component of the gentamicin C complex, gentamicin C2a which then undergoes an epimerization by GenB2 and then a N-methylation by an unconfirmed gene to form the final product in this branch point, gentamicin C1.<ref name="TestaII" /><ref name="Guo" /><ref name="Kumar" /><ref name="Chen" />
			When X<sub>2</sub> bypasses GenK and is directly ] and ] by the GenQ enzyme, the other pharmacologically relevant intermediate JI-20A is formed.<ref name="Kumar" /><ref name="Guo"/> Although, there has been identification of an intermediate for this step, 6'-dehydro-6'-oxo-gentamicin X2 (6'-DOX), for which the enzyme GenB1 is purposed as the ] enzyme.<ref name="Guo" /> JI-20A is then ] into the first component of the gentamicin C complex for this branch, gentamicin C1a via a catalytic reaction with GenB4.<ref name="Chen">{{cite journal | vauthors = Chen X, Zhang H, Zhou S, Bi M, Qi S, Gao H, Ni X, Xia H | title = The bifunctional enzyme, GenB4, catalyzes the last step of gentamicin 3',4'-di-deoxygenation via reduction and transamination activities | journal = Microbial Cell Factories | volume = 19 | issue = 1 | pages = 62 | date = March 2020 | pmid = 32156271 | pmc = 7063804 | doi = 10.1186/s12934-020-01317-0 | doi-access = free }}</ref> C1a then undergoes an N-methylation by an unconfirmed enzyme to form the final component, gentamicin C2b.<ref name="Guo" /><ref name="TestaII" /><ref name="Kumar" /><ref name="Chen" />
			====Fermentation====
			Gentamicin is only synthesized via submerged ] and inorganic sources of nutrients have been found to reduce production.<ref name="Kumar">{{cite journal | vauthors = Kumar CG, Himabindu M, Jetty A | title = Microbial biosynthesis and applications of gentamicin: a critical appraisal | journal = Critical Reviews in Biotechnology | volume = 28 | issue = 3 | pages = 173–212 | date = January 2008 | pmid = 18937107 | doi = 10.1080/07388550802262197 | s2cid = 83784820 }}</ref> Traditional fermentation used yeast beef broth,<ref name="Weinstein" /> but there has been research into optimizing the ] for producing gentamicin C complex due to the C complex currently being the only pharmaceutically relevant component.<ref name="Kumar" /> The main components of the growth medium are carbon sources, mainly sugars, but several studies found increased gentamicin production by adding vegetable and fish oils and decreased gentamicin production with the addition of ], ] and several ]s.<ref name="Kumar" /> ] and various forms of yeast and yeast derivatives are traditionally used as the nitrogen source in the growth medium, but several ], ], ], ], and ] have proven to be beneficial additives.<ref name="Kumar" /><ref name ="Daniels">{{cite journal | vauthors = Daniels PJ, Luce C, Nagabhushan TL | title = The gentamicin antibiotics. 6. Gentamicin C2b, an aminoglycoside antibiotic produced by Micromonospora purpurea mutant JI-33 | journal = The Journal of Antibiotics | volume = 28 | issue = 1 | pages = 35–41 | date = January 1975 | pmid = 1092638 | doi = 10.7164/antibiotics.28.35 | doi-access = free }}</ref> ]s, ] (] and a few others at low concentration), various vitamins (mostly ]), ] are also supplemented into the growth medium to increase gentamicin production, but the margin of increase is dependent on the species of ''Micromonospora'' and the other components in the growth medium.<ref name="Kumar" /><ref name ="Wagman">{{cite journal | vauthors = Wagman GH, Testa RT, Marquez JA | title = Antibiotic 6640. II. Fermentation, isolation, and properties | journal = The Journal of Antibiotics | volume = 23 | issue = 11 | pages = 555–558 | date = November 1970 | pmid = 5487130 | doi = 10.7164/antibiotics.23.555 | doi-access = free }}</ref> With all of these aforementioned additives, ] and ] are key determining factors for the amount of gentamicin produced.<ref name="Kumar" /><ref name="Daniels" /> A range of pH from 6.8 to 7.5 is used for gentamicin biosynthesis and the aeration is determined by independent experimentation reliant on type of growth medium and species of ''Micromonospora''.<ref name="Kumar" /><ref name="Daniels" />
			==History==
			]
			Gentamicin is produced by the fermentation of '']''. It was discovered in 1963 by Weinstein, Wagman et al. at Schering Corporation in Bloomfield, N.J. while working with source material (soil samples) provided by Rico Woyciesjes.<ref name="pmid14184912" /> When ''M.&nbsp;purpurea'' grows in culture it is a vivid purple colour similar to the colour of the dye ] and hence this was why Gentamicin took then name it did. Subsequently, it was purified and the structures of its three components were determined by Cooper, et al., also at the Schering Corporation. It was initially used as a topical treatment for burns at burn units in Atlanta and San Antonio and was introduced into IV usage in 1971. It remains a mainstay for use in ].{{cn|date=March 2023}}
			It is synthesized by '']'', a genus of ] widely present in the environment (water and soil). According to the ] Committee on Generic Names, antibiotics not produced by ''Streptomyces'' should not use ''y'' in the ending of the name, and to highlight their specific biological origins, gentamicin and other related antibiotics produced by this genus (], ], ], ], and ]) have their spellings ending in ''~micin'' and not in ''~mycin''.<ref>{{cite journal | vauthors = Waisbren BA | title = Experiences with the new antibiotic gentamicin | journal = The Journal of Infectious Diseases | volume = 119 | issue = 4 | pages = 518–536 | date = 1 April 1969 | pmid = 4306977 | doi = 10.1093/infdis/119.4-5.528 }}</ref>
			==Research==
			Gentamicin is also used in ] research as an antibacterial agent in tissue and cell culture, to prevent contamination of sterile cultures. Gentamicin is one of the few heat-stable antibiotics that remain active even after ], which makes it particularly useful in the preparation of some microbiological growth media.{{citation needed|date=September 2015}}
			== References ==
	{{Reflist}}		{{Reflist}}
	*
			== Further reading ==
	*
			{{refbegin}}
			* {{cite book | title=Medical Genetics Summaries | chapter=Gentamicin Therapy and MT-RNR1 Genotype | chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK285956/ | veditors=Pratt VM, McLeod HL, Rubinstein WS, Scott SA, Dean LC, Kattman BL, Malheiro AJ | publisher=] (NCBI) | year=2015 | pmid=28520359 | id=Bookshelf ID: NBK285956 | vauthors=Dean L | url=https://www.ncbi.nlm.nih.gov/books/NBK61999/ }}
			{{refend}}
	{{Antibiotics and chemotherapeutics for dermatological use}}		{{Antibiotics and chemotherapeutics for dermatological use}}
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