Array ( [0] => {{Short description|Chemical compound}} [1] => {{Use dmy dates|date=January 2024}} [2] => {{Infobox drug [3] => | verifiedrevid = 470611185 [4] => | image = Tobramycin.svg [5] => | width = 200 [6] => | alt = [7] => | image2 = Tobramycin 1lc4.png [8] => | width2 = [9] => | alt2 = [10] => | caption = [11] => [12] => [13] => | pronounce = [14] => | tradename = Nebcin, Tobrex, Tobi, others [15] => | Drugs.com = {{drugs.com|monograph|tobramycin-sulfate}} [16] => | MedlinePlus = a682660 [17] => | DailyMedID = Tobramycin [18] => | pregnancy_AU = D [19] => | pregnancy_AU_comment ={{cite web | title=Tobramycin Use During Pregnancy | website=Drugs.com | date=11 November 2019 | url=https://www.drugs.com/pregnancy/tobramycin.html | access-date=28 April 2020}}{{cite web | title=Tobramycin ophthalmic Use During Pregnancy | website=Drugs.com | date=24 December 2019 | url=https://www.drugs.com/pregnancy/tobramycin-ophthalmic.html | access-date=28 April 2020}} [20] => | pregnancy_category = [21] => | routes_of_administration = [[intravenous infusion|Intravenous]], [[intramuscular injection|intramuscular]], [[inhalation]], [[Ophthalmic drug administration|ophthalmic]] [22] => | class = [23] => | ATC_prefix = J01 [24] => | ATC_suffix = GB01 [25] => | ATC_supplemental = {{ATC|S01|AA12}} [26] => [27] => [28] => | legal_AU = S4 [29] => | legal_AU_comment = {{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}} [30] => | legal_BR = [31] => | legal_BR_comment = [32] => | legal_CA = Rx-only [33] => | legal_CA_comment = {{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}} [34] => | legal_DE = [35] => | legal_DE_comment = [36] => | legal_NZ = [37] => | legal_NZ_comment = [38] => | legal_UK = POM [39] => | legal_UK_comment = {{cite web | title=Tobramycin 40mg/ml Injection – Summary of Product Characteristics (SmPC) | website=(emc) | date=9 October 2018 | url=https://www.medicines.org.uk/emc/medicine/6566#INDICATIONS | access-date=28 April 2020}} [40] => | legal_US = Rx-only [41] => | legal_US_comment = [42] => | legal_EU = Rx-only [43] => | legal_EU_comment = [44] => | legal_UN = [45] => | legal_UN_comment = [46] => | legal_status = Rx-only [47] => [48] => [49] => | bioavailability = [50] => | protein_bound = Not bound{{cite book|title=Austria-Codex|veditors = Haberfeld H|at=Tobramycin B. Braun 1 mg/ml Infusionslösung|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2021|language=German}} [51] => | metabolism = Not metabolized [52] => | metabolites = [53] => | onset = [54] => | elimination_half-life = 2–3 hrs [55] => | duration_of_action = [56] => | excretion = Exclusively via kidneys [57] => [58] => [59] => | CAS_number_Ref = {{cascite|correct|??}} [60] => | CAS_number = 32986-56-4 [61] => | CAS_supplemental = [62] => | PubChem = 36294 [63] => | IUPHAR_ligand = [64] => | DrugBank_Ref = {{drugbankcite|correct|drugbank}} [65] => | DrugBank = DB00684 [66] => | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} [67] => | ChemSpiderID = 33377 [68] => | UNII_Ref = {{fdacite|correct|FDA}} [69] => | UNII = VZ8RRZ51VK [70] => | KEGG_Ref = {{keggcite|correct|kegg}} [71] => | KEGG = D00063 [72] => | KEGG2_Ref = {{keggcite|correct|kegg}} [73] => | KEGG2 = C00397 [74] => | ChEBI_Ref = {{ebicite|correct|EBI}} [75] => | ChEBI = 28864 [76] => | ChEMBL_Ref = {{ebicite|correct|EBI}} [77] => | ChEMBL = 1747 [78] => | NIAID_ChemDB = [79] => | PDB_ligand = TOY [80] => | synonyms = 47663, SPRC-AB01 [81] => [82] => [83] => | IUPAC_name = (2''S'',3''R'',4''S'',5''S'',6''R'')-4-amino-2-{[(1''S'',2''S'',3''R'',4''S'',6''R'')-4,6-diamino-3-{[(2''R'',3''R'',5''S'',6''R'')-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol [84] => | C=18 | H=37 | N=5 | O=9 [85] => | SMILES = C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H](C[C@@H]([C@H](O3)CN)O)N)N [86] => | Jmol = [87] => | StdInChI_Ref = {{stdinchicite|correct|chemspider}} [88] => | StdInChI = 1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1 [89] => | StdInChI_comment = [90] => | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} [91] => | StdInChIKey = NLVFBUXFDBBNBW-PBSUHMDJSA-N [92] => | density = [93] => | density_notes = [94] => | melting_point = [95] => | melting_high = [96] => | melting_notes = [97] => | boiling_point = [98] => | boiling_notes = [99] => | solubility = [100] => | sol_units = [101] => | specific_rotation = [102] => }} [103] => [104] => [105] => '''Tobramycin''' is an [[aminoglycoside]] [[antibiotic]] derived from ''[[Streptomyces tenebrarius]]'' that is used to treat various types of [[bacteria]]l infections, particularly [[Gram-negative]] infections. It is especially effective against species of ''[[Pseudomonas]]''.{{ cite web | title = Tobramycin | url = http://www.toku-e.com/Upload/Products/PDS/20120515001224.pdf | publisher = Toku-E | date = 12 January 2010 | access-date = 11 June 2012 }} [106] => [107] => [108] => It was patented in 1965, and approved for medical use in 1974.{{cite book | vauthors = Fischer J, Ganellin CR | name-list-style = vanc |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=507 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA507 |language=en}} It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }} In 2021, it was the 299th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}{{cite web | title = Tobramycin - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Tobramycin | access-date = 14 January 2024}} [109] => [110] => == Medical uses == [111] => Like all aminoglycosides, tobramycin does not pass the [[gastro-intestinal tract]], so for [[Systemic administration|systemic]] use it can only be given [[Intravenous therapy|intravenously]] or by [[Intramuscular injection|injection into a muscle]]. Eye drops and ointments (tobramycin only, Tobrex, or combined with [[dexamethasone]], sold as Tobradex) and [[nebuliser|nebulised]] formulations both have low [[Absorption (pharmacokinetics)|systemic absorption]]. The formulation for injection is branded Nebcin. The nebulised formulation (brand name Tobi) is indicated in the treatment of [[exacerbation]]s of chronic infection with ''[[Pseudomonas aeruginosa]]'' in people diagnosed with [[cystic fibrosis]].{{cite web | title=Tobi- tobramycin solution | website=DailyMed | date=5 October 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=94f9e516-6bf6-4e30-8dde-8833c25c2560 | access-date=28 April 2020}}{{cite web | title=Tobi Podhaler | website=[[European Medicines Agency]] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/tobi-podhaler | access-date=28 April 2020}} {{PD-notice}} [112] => [113] => Tobramycin eye drops (with or without dexamethasone) are indicated in the treatment of superficial infections of the eye, such as [[conjunctivitis|bacterial conjunctivitis]].{{cite web | title=Tobrex- tobramycin ointment | website=DailyMed | date=16 September 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cdd423c5-a231-47d4-bf51-00b5c29e6a60 | access-date=28 April 2020}}{{cite web | title=Tobradex Eye Drops – Summary of Product Characteristics (SmPC) | website=(emc) | date=21 January 2020 | url=https://www.medicines.org.uk/emc/product/1324/smpc | access-date=28 April 2020}}{{cite web | title=Tobradex- tobramycin and dexamethasone ointment | website=DailyMed | date=11 September 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5538d748-215c-4e3e-b940-ac9baf07d8a1 | access-date=28 April 2020}}{{cite web | title=Tobradex- tobramycin and dexamethasone suspension/ drops | website=DailyMed | date=9 September 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=22b59456-d26a-4f23-b052-3d73e00181eb | access-date=28 April 2020}} [114] => [115] => Tobramycin, in its injectable form, is also indicated for various severe or life-threatening infections caused by susceptible strains: [[sepsis]], [[meningitis]], [[lower respiratory tract infection]]s, [[intra-abdominal infection]]s, [[skin infection]]s, [[Osteomyelitis|bone infections]], and [[Skin and skin structure infection|skin structure infections]], complicated and recurrent [[urinary tract infection]]s.{{cite web | title=Tobramycin- tobramycin sulfate injection, powder, for solution | website=DailyMed | date=11 October 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d62ff359-912b-4be1-9fc2-2dde8777eefb | access-date=28 April 2020}} [116] => [117] => === Spectrum of susceptibility === [118] => Tobramycin has a narrow spectrum of activity and is active against Gram-positive ''[[Staphylococcus aureus]]'' and various Gram-negative bacteria. Clinically, tobramycin is frequently used to eliminate ''[[Pseudomonas aeruginosa]]'' in [[cystic fibrosis]] patients. {{cn|date=March 2023}}The following represents the [[minimum inhibitory concentration]] (MIC) susceptibility data for a few strains of ''Pseudomonas aeruginosa'': [119] => * ''Pseudomonas aeruginosa'' - <0.25 µg/mL – 92 µg/mL{{medical citation needed|date=February 2024}} [120] => * ''Pseudomonas aeruginosa'' (non-mucoid) – 0.5 µg/mL - >512 µg/mL{{medical citation needed|date=February 2024}} [121] => * ''Pseudomonas aeruginosa'' (ATCC 27853) – 0.5 µg/mL – 2 µg/mL{{cite web | title = Tobramycin Susceptibility and Minimum Inhibitory Concentration (MIC) Data | url = http://www.toku-e.com/Assets/MIC/Tobramycin.pdf | work = Toku-E }} [122] => The MIC for ''[[Klebsiella pneumoniae]], KP-1'', is 2.3±0.2 µg/mL at 25 °C [unpublished]{{clarify|date=February 2024}}.{{medical citation needed|date=February 2024}} [123] => [124] => == Contraindications == [125] => Tobramycin is contraindicated in people with [[hypersensitivity]] against aminoglycoside antibiotics.{{cite book|title=Austria-Codex|veditors = Haberfeld H|at=Tobrex Augentropfen|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2021|language=German}} The Infusion is also contraindicated in people with [[myasthenia gravis]]. [126] => [127] => == Side effects == [128] => Like other aminoglycosides, a major side effect for tobramycin is [[ototoxicity]] or a loss of [[equilibrioception]], or both in genetically susceptible individuals.{{cite journal | vauthors = Lerner AM, Reyes MP, Cone LA, Blair DC, Jansen W, Wright GE, Lorber RR | title = Randomised, controlled trial of the comparative efficacy, auditory toxicity, and nephrotoxicity of tobramycin and netilmicin | journal = Lancet | volume = 1 | issue = 8334 | pages = 1123–6 | date = May 1983 | pmid = 6133153 | doi = 10.1016/S0140-6736(83)92864-7 | s2cid = 8303933 }} Other side effects include nephrotoxicity, neuromuscular toxicity, and hypersensitivity reactions.{{cite journal | vauthors = Neu HC | title = Tobramycin: an overview | journal = The Journal of Infectious Diseases | volume = 134 | issue = Suppl | pages = S3–19 | date = August 1976 | pmid = 787451 | doi = 10.1093/infdis/134.supplement_1.s3 | jstor = 30106949 }} Nephrotoxicity can be particularly worrisome when multiple doses accumulate over the course of a treatment{{cite journal | vauthors = Pedersen SS, Jensen T, Osterhammel D, Osterhammel P | title = Cumulative and acute toxicity of repeated high-dose tobramycin treatment in cystic fibrosis | journal = Antimicrobial Agents and Chemotherapy | volume = 31 | issue = 4 | pages = 594–9 | date = April 1987 | pmid = 3606063 | pmc = 174783 | doi = 10.1128/AAC.31.4.594 }} or when the kidney concentrates urine by increasing [[Renal physiology|tubular reabsorption]] during sleep. Adequate hydration may help prevent excess nephrotoxicity and subsequent loss of renal function.{{Cite book | vauthors = Reyhanoglu G, Reddivari AK | chapter = Tobramycin| chapter-url = https://www.ncbi.nlm.nih.gov/books/NBK551695/| title = StatPearls | location = Treasure Island (FL) | publisher = StatPearls Publishing | date = January 2022 | pmid = 31869159 }} For these reasons [[wikt:parenteral|parenteral]] tobramycin needs to be carefully dosed by [[body weight]], and its serum concentration monitored. Tobramycin is thus said to be a drug with a narrow [[therapeutic index]].{{cn|date=March 2023}} [129] => [130] => == Interactions == [131] => [[Muscle relaxant]]s and [[diethylether]] can add to the [[Neuromuscular-blocking drug|neuromuscular blocking]] effects of tobramycin. [132] => [133] => [[Methoxyflurane]], when used as an [[inhalational anesthetic]], can aggravate the nephrotoxic effects of injected tobramycin. Likewise, combining injected tobramycin with other nephrotoxic or ototoxic drugs can lead to more adverse effects; examples include [[amphotericin B]], [[ciclosporin]], [[cisplatin]], [[vancomycin]], and the [[diuretic]] [[furosemide]]. Other diuretics can also increase the risk for side effects because they raise tobramycin concentrations in the body fluids. [134] => [135] => Combining tobramycin with [[betalactam antibiotic]]s can be desirable because of their synergistic effects. However, when they are given through the same drip, as well as in people with reduced kidney function, they can react with each other to form antibiotically inactive [[amide]]s. [136] => [137] => == Pharmacology == [138] => === Mechanism of action === [139] => Tobramycin works by binding to a site on the bacterial [[30S]] and [[50S]] [[ribosome]], preventing formation of the 70S complex.{{cite journal | vauthors = Yang G, Trylska J, Tor Y, McCammon JA | title = Binding of aminoglycosidic antibiotics to the oligonucleotide A-site model and 30S ribosomal subunit: Poisson-Boltzmann model, thermal denaturation, and fluorescence studies | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 18 | pages = 5478–90 | date = September 2006 | pmid = 16942021 | doi = 10.1021/jm060288o }} As a result, [[mRNA]] cannot be [[Translation (biology)|translated]] into protein, and cell death ensues.{{cite journal | vauthors = Haddad J, Kotra LP, Llano-Sotelo B, Kim C, Azucena EF, Liu M, Vakulenko SB, Chow CS, Mobashery S | display-authors = 6 | title = Design of novel antibiotics that bind to the ribosomal acyltransfer site | journal = Journal of the American Chemical Society | volume = 124 | issue = 13 | pages = 3229–37 | date = April 2002 | pmid = 11916405 | doi = 10.1021/ja011695m }} Tobramycin also binds to RNA-[[aptamer]]s,{{cite journal | vauthors = Kotra LP, Haddad J, Mobashery S | title = Aminoglycosides: perspectives on mechanisms of action and resistance and strategies to counter resistance | journal = Antimicrobial Agents and Chemotherapy | volume = 44 | issue = 12 | pages = 3249–56 | date = December 2000 | pmid = 11083623 | pmc = 90188 | doi = 10.1128/aac.44.12.3249-3256.2000 }} artificially created molecules to bind to certain targets. However, there seems to be no indication that Tobramycin binds to natural [[RNA]]s or other [[nucleic acid]]s.{{cn|date=March 2023}} [140] => [141] => The effect of tobramycin can be inhibited by metabolites of the [[Citric acid cycle|Krebs (TCA) cycle]], such as [[Glyoxylic acid|glyoxylate]]. These metabolites protect against tobramycin lethality by diverting carbon flux away from the TCA cycle, collapsing [[cellular respiration]], and thereby inhibiting Tobramycin uptake and thus lethality.{{cite journal | vauthors = Meylan S, Porter CB, Yang JH, Belenky P, Gutierrez A, Lobritz MA, Park J, Kim SH, Moskowitz SM, Collins JJ | display-authors = 6 | title = Carbon Sources Tune Antibiotic Susceptibility in Pseudomonas aeruginosa via Tricarboxylic Acid Cycle Control | journal = Cell Chemical Biology | volume = 24 | issue = 2 | pages = 195–206 | date = February 2017 | pmid = 28111098 | pmc = 5426816 | doi = 10.1016/j.chembiol.2016.12.015 }} [142] => [143] => === Pharmacokinetics === [144] => Tobramycin is not absorbed in the gut. When given as infusion, it is distributed in the extracellular fluid. It can accumulate in the kidney's [[tubular cells]] and in the lymph of the inner ear. Only low concentrations reach the [[central nervous system]] and breast milk. Tobramycin passes the placenta: in the fetus, 20% of the mother's concentrations have been measured. [145] => [146] => The substance is neither bound to [[plasma protein]]s, nor is it metabolized. It is excreted in unchanged form via the kidneys with a [[biological half-life]] of about 2 to 3 hours. Elimination from deep [[compartment (pharmacokinetics)|compartments]] such as the [[renal cortex]] follows after 8 to 12 hours. In newborns the half-life is 4.6 hours on average; in those with a low birth weight it is as long as 8.7 hours on average. People with reduced kidney function also have a longer half-life for tobramycin, while in those with severe [[burn]]s it can be shorter. [147] => [148] => == Society and culture == [149] => Tobramycin was patented in 1965, and approved for medical use in 1974. [150] => [151] => Tobramycin in the form of eye drops is available in Bulgaria, Hungary, the United States, and Canada by prescription only, whereas in the other countries it may be available over the counter.{{cn|date=February 2024}} [152] => [153] => Tobrex eye drops are a 0.3% tobramycin sterile ophthalmic solution produced by [[Alcon]] Pharmaceuticals. [[Benzalkonium chloride]] 0.01% is added to Tobrex as a preservative.{{cn|date=February 2024}} [154] => [155] => In Egypt, tobramycin (in the form of eye drops) is sold under the brand Tobrin, produced by [[EIPICo]].{{cn|date=February 2024}} [156] => [157] => Tobramycin is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]]. [158] => [159] => In 2021, tobramycin was the 299th most commonly prescribed medication in the United States, with more than 500,000 prescriptions. [160] => [161] => == References == [162] => {{Reflist}} [163] => [164] => == Further reading == [165] => * {{cite journal | vauthors = Davis BD | title = Mechanism of bactericidal action of aminoglycosides | journal = Microbiological Reviews | volume = 51 | issue = 3 | pages = 341–50 | date = September 1987 | pmid = 3312985 | pmc = 373115 | doi = 10.1128/MMBR.51.3.341-350.1987 }} [166] => [167] => {{AminoglycosideAntiBiotics}} [168] => {{Portal bar | Medicine}} [169] => [170] => [[Category:Aminoglycoside antibiotics]] [171] => [[Category:Drugs developed by Novartis]] [] => )
good wiki

Tobramycin

{{Infobox drug | verifiedrevid = 470611185 | image = Tobramycin. svg | width = 200 | alt = | image2 = Tobramycin 1lc4.

More about us

About

Expert Team

Vivamus eget neque lacus. Pellentesque egauris ex.

Award winning agency

Lorem ipsum, dolor sit amet consectetur elitorceat .

10 Year Exp.

Pellen tesque eget, mauris lorem iupsum neque lacus.

You might be interested in

Antibiotic

Antibiotics are a class of drugs that are used to treat and prevent bacterial infections in humans and animals.

Bacteria

Bacteria are single-celled microorganisms that have a wide range of shapes and sizes.

Cisplatin

Cisplatin is an anticancer medication that is commonly used in the treatment of various types of cancer, including testicular, ovarian, bladder, and lung cancer.

MRNA

Messenger RNA (mRNA) is a single-stranded molecule that plays a crucial role in the process of protein synthesis.

Ribosome

The Wikipedia page on Ribosome provides an in-depth description of this essential cellular component responsible for protein synthesis.

RNA

RNA (Ribonucleic acid) is a molecule that is essential for life and plays a crucial role in protein synthesis, gene regulation, and other cellular processes.

Sepsis

Sepsis is a life-threatening condition that occurs when the body's response to an infection damages its own tissues and organs.

Vancomycin

Vancomycin is a widely used antibiotic medication that is primarily used for the treatment of serious bacterial infections, particularly those caused by methicillin-resistant Staphylococcus aureus (MRSA) and other resistant bacteria.