Gentamicin - wikipedia Gentamicin Gentamicin Clinical data Pronunciation / ˌdʒɛntəˈmaɪsən / Trade names Cidomycin, Septopal, Genticyn, Garamycin, others AHFS / Drugs.com Monograph MedlinePlus a682275 Pregnancy category Routes of administration IV, eye drop, IM, topical ATC code D06AX07 ( WHO ) J01GB03 ( WHO ) S01AA11 ( WHO ) S02AA14 ( WHO ) S03AA06 ( WHO ) QA07AA91 ( WHO ) QG01AA91 ( WHO ) QG51AA04 ( WHO ) QJ51GB03 ( WHO ) Legal status Legal status In general : ℞ ( Prescription only ) Pharmacokinetic data Bioavailability limited bioavailability by mouth Protein binding 0 -- 10 % Biological half - life 2 h Excretion renal Identifiers IUPAC name ( 3R, 4R, 5R ) - 2 - ( ( ( 1S, 2S, 3R, 4S, 6R ) - 4, 6 - diamino - 3 - ( ( ( 2R, 3R, 6S ) - 3 - amino - 6 - ( ( 1R ) - 1 - ( methylamino ) ethyl ) oxan - 2 - yl ) oxy ) - 2 - hydroxycyclohexyl ) oxy ) - 5 - methyl - 4 - ( methylamino ) oxane - 3, 5 - diol CAS Number 1403 - 66 - 3 PubChem CID 3467 IUPHAR / BPS 2427 DrugBank DB00798 ChemSpider 390067 UNII T6Z9V48IKG KEGG D08013 ChEBI CHEBI : 27412 ChEMBL CHEMBL195892 ECHA InfoCard 100.014. 332 Chemical and physical data Formula Molar mass 477.596 g / mol 3D model ( JSmol ) Interactive image 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 InChI InChI = 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 Key : CEAZRRDELHUEMR - URQXQFDESA - N ( what is this ? ) ( verify ) Gentamicin, sold under brand names Garamycin among others, is an antibiotic used to treat several types of bacterial infections. This may include bone infections, endocarditis, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, and sepsis among others. It is not effective for gonorrhea or chlamydia infections. It can be given intravenously, by injection into a muscle, or topically. Topical formulations may be used in burns or for infections of the outside of the eye. In the developed world it is often only used for two days until bacterial cultures determine what antibiotics the infection is sensitive to. The dose required should be monitored by blood testing. Gentamicin can cause inner ear problems and kidney problems. The inner ear problems can include problems with balance and problems with hearing. These problems may be permanent. If used during pregnancy it can cause harm to the baby. It appears to be safe for use during breastfeeding. Gentamicin is a type of aminoglycoside. It works by stopping the bacteria from making protein, which typically kills the bacteria. Gentamicin was discovered in 1963. It is made from the bacteria Micromonospora purpurea. Gentamicin is on the World Health Organization 's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The injectable 's wholesale cost in the developing world in 2014 was between US $ 0.05 and US $0.58 per ml. Contents 1 Medical uses 2 Adverse effects 2.1 Kidney damage 2.2 Inner ear 3 Mechanism of action 3.1 Components 4 Contraindications 5 Special populations 5.1 Pregnancy and breastfeeding 5.2 Geriatrics 5.3 Pediatrics 6 History 7 Research 8 References Medical uses Active against a wide range of bacterial infections, mostly Gram - negative bacteria including Pseudomonas, Proteus, Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes, Serratia, and the Gram - positive Staphylococcus. Gentamicin is used in the treatment of respiratory tract infections, urinary tract infections, blood, bone and soft tissues infections of these susceptible bacteria. Gentamicin is not used for Neisseria gonorrhoeae, Neisseria meningitidis or Legionella pneumophila bacterial infections ( because of the risk of the person going into shock from lipid A endotoxin found in certain Gram - negative organisms ). Gentamicin is also useful against Yersinia pestis, its relatives, and Francisella tularensis ( the organism responsible for Tularemia seen often in hunters and / or trappers ). Some Enterobacteriaceae, Pseudomonas spp., Enterococci, Staphylococcus aureus and other Staphylococci are resistant to gentamicin sulfate, to varying degrees. Adverse effects Adverse effects of gentamicin can range from less severe reactions such as nausea and vomiting to more severe reactions such as : Low blood counts Allergic responses Neuromuscular problems Nerve damage Kidney damage ( nephrotoxicity ) Ear disorders ( ototoxicity ) Nephrotoxicity and ototoxicity are thought to be dose related with higher doses causing greater chance of toxicity. These two toxicities may have delayed presentation, sometimes not appearing until after completing treatment. Kidney damage Kidney damage is a problem in 10 - 25 % of people who receive aminoglycosides, and gentamicin is one of the most nephrotoxic of the class. Oftentimes acute nephrotoxicity is reversible, but it may be fatal. The risk of nephrotoxicity can be affected by the dose, frequency, duration of therapy, and concurrent use of certain medications such as NSAIDs, diuretics, cisplatin, ciclosporin, cephalosporin, amphotericin, iodide contrast media, and vancomycin. Factors that increase risk of nephrotoxicity include : Increased age Reduced renal function Pregnancy Hypothyroidism Hepatic dysfunction Volume depletion Metabolic acidosis Sodium depletion Kidney dysfunction is monitored by measuring creatinine in the blood, electrolyte levels, low urine output, foamy urine, and concentrations of other chemicals in the blood. Inner ear 11 % of the population who receives aminoglycosides experience damage to their inner ear. The common symptoms of inner ear damage are : tinnitus, hearing loss, vertigo, trouble with coordination, dizziness. 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 inner ear vestibular apparatus can lead to balance problems. To reduce the risk of ototoxicity it is recommended to stay hydrated. Factors that increase risk of inner ear damage include : High blood uric acid levels Kidney dysfunction Liver dysfunction Higher doses Long courses of therapy Elderly Also taking strong diuretics ( e.g. furosemide ) Mechanism of action Gentamicin is a bactericidal antibiotic that works by irreversibly binding the 30S subunit of the bacterial ribosome, interrupting protein synthesis. This mechanism of action is similar to other aminoglycosides. Components Gentamicin is composed of a number of related gentamicin components and fractions which have varying degrees of antimicrobial potency. The main components of gentamicin include members of the gentamicin C complex : gentamicin C1, gentamicin C1a, and gentamicin C2 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. 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. Contraindications Gentamicin should not be used if a person has a history of hypersensitivity such as anaphylaxis shock or other serious toxic reaction to gentamicin or any other aminoglycosides. Special populations Pregnancy and breastfeeding Gentamicin is not recommended in pregnancy unless the benefits outweigh the risks for the mother. Gentamicin can cross the placenta and several reports of irreversible bilateral congenital deafness in children have been seen. Intramuscular injection of gentamicin in mothers can cause muscle weakness in the newborn. 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. Geriatrics Renal function should be assessed before beginning therapy and during in elderly due to a decline in glomerular filtration rate. This population can have longer than usual gentamicin levels in the body. Use cautiously in persons with renal, auditory, vestibular, or neuromuscular dysfunction. Pediatrics Gentamicin may not be appropriate to use in children, including newborns and infants. Studies have shown higher serum levels and a longer half - life in this population. Check renal function periodically during therapy. Hypocalcemia, hypokalemia, and muscle weakness have been reported after gentamicin injection. History Gentamicin for injection Gentamicin is produced by the fermentation of Micromonospora purpurea. It was discovered in 1963 by Weinstein, Wagman et al. at Schering Corporation in Bloomfield, N.J. working with source material ( soil samples ) provided by Rico Woyciesjes. Subsequently, it was purified and the structures of its three components determined by Cooper, et al., also at the Schering Corporation. It was initially used as a topical treatment for burns at the Atlanta and San Antonio burn units and was introduced into IV usage in 1971. It remains a mainstay for use in sepsis. It is synthesized by Micromonospora, a genus of Gram - positive bacteria widely present in the environment ( water and soil ). To highlight their specific biological origins, gentamicin and other related antibiotics produced by this genus ( verdamicin, mutamicin, sisomicin, netilmicin, and retymicin ) generally have their spellings ending in ~ micin and not in ~ mycin. Research Gentamicin is also used in molecular biology 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 autoclaving, which makes it particularly useful in the preparation of some microbiological growth media. References ^ Jump up to : `` Gentamicin sulfate ''. The American Society of Health - System Pharmacists. Archived from the original on 2015 - 08 - 16. Retrieved Aug 15, 2015. Jump up ^ Bartlett, Jimmy ( 2013 ). Clinical Ocular Pharmacology ( s ed. ). Elsevier. p. 214. ISBN 9781483193915. Archived from the original on 2015 - 12 - 22. Jump up ^ Moulds, Robert ; Jeyasingham, Melanie ( October 2010 ). `` Gentamicin : a great way to start ''. Australian Prescriber ( 33 ) : 134 -- 135. Archived from the original on 2011 - 03 - 13. Jump up ^ `` Gentamicin use while breastfeeding ''. Archived from the original on 6 September 2015. Retrieved 15 August 2015. Jump up ^ Pucci, edited by Thomas Dougherty, Michael J. ; Weinstein, Marvin J. ( 2011 ). Handbook of antibiotic discovery and development ( 2012 ed. ). New York : Springer. p. 238. ISBN 9781461413998. Archived from the original on 2016 - 03 - 11. CS1 maint : Extra text : authors list ( link ) Jump up ^ `` WHO Model List of Essential Medicines ( 19th List ) '' ( PDF ). World Health Organization. April 2015. Archived ( PDF ) from the original on 13 December 2016. Retrieved 8 December 2016. Jump up ^ Burchum, Jacqueline ( 2014 ). Lehne 's pharmacology for nursing care. Elsevier Health Sciences. p. 1051. ISBN 9780323340267. Archived from the original on 2016 - 03 - 11. Jump up ^ `` Gentamicin sulfate ''. International Drug Price Indicator Guide. Retrieved 15 August 2015. ^ Jump up to : `` Gentamicin '' ( PDF ). Baxter Corporation. Archived ( PDF ) from the original on 4 March 2016. Retrieved 2 November 2015. ^ Jump up to : `` Product Monograph '' ( PDF ). Sandoz Canada Inc. Archived ( PDF ) from the original on 12 April 2015. Retrieved 2 November 2015. Jump up ^ Goljan, Edward F. ( 2011 ). Rapid Review Pathology ( 3rd ed. ). Philadelphia, Pennsylvania : Elsevier. p. 241. ISBN 978 - 0 - 323 - 08438 - 3. Jump up ^ `` Gentamicin spectrum of bacterial susceptibility and Resistance '' ( PDF ). Archived ( PDF ) from the original on 20 February 2015. Retrieved 15 May 2012. ^ Jump up to : Lopez - Novoa, Jose M ; Quiros, Yaremi ; Vicente, Laura ; Morales, Ana I ; Lopez - Hernandez, Francisco J ( Jan 2011 ). `` New insights into the mechanism of aminoglycoside nephrotoxicity : an integrative point of view ''. Kidney International. 79 ( 1 ) : 33 -- 45. PMID 20861826. doi : 10.1038 / ki. 2010.337. Archived from the original on 2016 - 03 - 10. Jump up ^ East, JE ; Foweraker, JE ; Murgatroyd, FD ( 2005 - 05 - 01 ). `` Gentamicin induced ototoxicity during treatment of enterococcal endocarditis : resolution with substitution by netilmicin ''. Heart. 91 ( 5 ) : e32. ISSN 1355 - 6037. PMC 1768868. PMID 15831617. doi : 10.1136 / hrt. 2003.028308. ^ Jump up to : Selimoglu, Erol ( 2007 - 01 - 01 ). `` Aminoglycoside - induced ototoxicity ''. Current Pharmaceutical Design. 13 ( 1 ) : 119 -- 126. ISSN 1873 - 4286. PMID 17266591. doi : 10.2174 / 138161207779313731. Jump up ^ `` DrugBank - Gentamicin ''. Archived from the original on 2013 - 10 - 04. Jump up ^ Weinstein, Marvin J. ( 1967 ). `` Biological Activity of the Antibiotic Components of the Gentamicin Complex ''. Journal of Bacteriology. 94.3 : 789 -- 790. access - date = requires url = ( help ) Jump up ^ Vydrin, A.F. ( 2003 ). `` Component Composition of Gentamicin Sulfate Preparations ''. Pharmaceutical Chemistry Journal. 37.8 : 448 -- 449. access - date = requires url = ( help ) Jump up ^ Isoherranen, Nina ; Eran, Lavy ( 2000 ). `` Pharmacokinetics of Gentamicin C, C, and C in Beagles after a Single Intravenous Dose ''. Antimicrobial Agents and Chemotherapy. 44.6 : 1443 -- 1447. doi : 10.1128 / aac. 44.6. 1443 - 1447.2000. Jump up ^ Weinstein, Marvin ; Wagman ( 1963 ). `` Gentamicin, A New Antimicrobial Complex from Micromonospora ''. J Med Chem. 6 : 463 -- 464. doi : 10.1021 / jm00340a034. Antibiotics and chemotherapeutics for dermatological use ( D06 ) Antibiotics Tetracycline and derivatives Demeclocycline Chlortetracycline Oxytetracycline Tetracycline Others Amphenicol : Chloramphenicol Aminoglycosides : Neomycin Gentamicin Amikacin Quinolone : Nadifloxacin Streptogramin : Virginiamycin Rifamycin : Rifaximin other : Fusidic acid Bacitracin Tyrothricin Mupirocin Chemotherapeutics Sulfonamides Silver sulfadiazine Sulfathiazole Mafenide Sulfamethizole Sulfanilamide Sulfamerazine Antivirals Aciclovir Penciclovir Idoxuridine Edoxudine Imiquimod Resiquimod Podophyllotoxin Docosanol Tromantadine Inosine Lysozyme Ibacitabine Lysine Other Ingenol mebutate Metronidazole Antibacterials : protein synthesis inhibitors ( J01A, J01B, J01F, J01G, QJ01XQ ) 30S Aminoglycosides ( initiation inhibitors ) - mycin ( Streptomyces ) Streptomycin Dihydrostreptomycin Neomycin Framycetin Paromomycin Ribostamycin Kanamycin Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin Hygromycin B Paromomycin - micin ( Micromonospora ) Gentamicin Netilmicin Sisomicin Plazomicin Isepamicin Verdamicin Astromicin Tetracycline antibiotics ( tRNA binding ) Tetracyclines Doxycycline Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline Glycylcyclines Tigecycline Fluorocyclines Eravacycline 50S Oxazolidinone ( initiation inhibitors ) Eperezolid Linezolid Posizolid Radezolid Ranbezolid Sutezolid Tedizolid Peptidyl transferase Amphenicols Chloramphenicol Azidamfenicol Thiamphenicol Florfenicol Pleuromutilins Retapamulin Tiamulin Valnemulin MLS ( transpeptidation / translocation ) Macrolides Azithromycin Clarithromycin Dirithromycin Erythromycin Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin Lincosamides Clindamycin Lincomycin Pirlimycin Streptogramins Pristinamycin Quinupristin / dalfopristin Virginiamycin EF - G Steroid antibacterials Fusidic acid WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Drugs used for diseases of the ear ( S02 ) Infection Acetic acid Aluminium acetotartrate Aluminium triacetate ( Burow 's solution ) Boric acid Chloramphenicol Chlorhexidine Ciprofloxacin Clioquinol Gentamicin Hydrogen peroxide Miconazole Neomycin Nitrofurazone Ofloxacin Polymyxin B Rifamycin Tetracycline Corticosteroids Betamethasone Dexamethasone Fluocinolone acetonide Hydrocortisone Prednisolone Analgesics and anesthetics Lidocaine Cocaine Phenazone Retrieved from `` https://en.wikipedia.org/w/index.php?title=Gentamicin&oldid=800494105 '' Categories : Aminoglycoside antibiotics World Health Organization essential medicines Toxicology Otologicals Hidden categories : CS1 maint : Extra text : authors list Pages using citations with accessdate and no URL Template : drugs.com link with non-standard subpage Drugs with non-standard legal status Articles with changed DrugBank identifier ECHA InfoCard ID from Wikidata Drugboxes which contain changes to verified fields All articles with unsourced statements Articles with unsourced statements from September 2015 RTT Talk Contents About Wikipedia Български Bosanski Català Čeština Deutsch Español فارسی Français Galego Hrvatski Italiano Kreyòl ayisyen Magyar Македонски Nederlands 日本 語 ଓଡ଼ିଆ پښتو Polski Português Русский Српски / srpski Srpskohrvatski / српскохрватски తెలుగు ไทย Українська 中文 Edit links This page was last edited on 13 September 2017, at 22 : 13. 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Question: gentamicin belongs to which class of antibacterial agents
Answer: aminoglycoside