Tobramycin

Tobramycin
Clinical data
Trade namesNebcin, Tobrex, Tobi, others
Other names47663, SPRC-AB01
AHFS/Drugs.comMonograph
MedlinePlusa682660
License data
Pregnancy
category
Routes of
administration		Intravenous, intramuscular, inhalation, ophthalmic
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein bindingNot bound[8]
MetabolismNot metabolized
Elimination half-life2–3 hrs
ExcretionExclusively via kidneys
Identifiers
  • (2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.046.642 Edit this at Wikidata
Chemical and physical data
FormulaC18H37N5O9
Molar mass467.520 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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 checkY
  • Key:NLVFBUXFDBBNBW-PBSUHMDJSA-N checkY
  (verify)

Tobramycin is an aminoglycoside antibiotic derived from Streptomyces tenebrarius that is used to treat various types of bacterial infections, particularly Gram-negative infections. It is especially effective against species of Pseudomonas.[9]

It was patented in 1965, and approved for medical use in 1974.[10] It is on the World Health Organization's List of Essential Medicines.[11] In 2021, it was the 299th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.[12][13]

  1. ^ "Tobramycin Use During Pregnancy". Drugs.com. 11 November 2019. Retrieved 28 April 2020.
  2. ^ "Tobramycin ophthalmic Use During Pregnancy". Drugs.com. 24 December 2019. Retrieved 28 April 2020.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  5. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  6. ^ "Tobramycin 40mg/mL Injection – Summary of Product Characteristics (SmPC)". (emc). 9 October 2018. Retrieved 28 April 2020.
  7. ^ "Tobi Podhaler EPAR". European Medicines Agency (EMA). 17 March 2003. Retrieved 10 August 2024.
  8. ^ Haberfeld H, ed. (2021). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Tobramycin B. Braun 1 mg/mL Infusionslösung.
  9. ^ "Tobramycin" (PDF). Toku-E. 12 January 2010. Retrieved 11 June 2012.
  10. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 507. ISBN 978-3-527-60749-5.{{cite book}}: CS1 maint: overridden setting (link)
  11. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  12. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  13. ^ "Tobramycin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.