Tobramycin

Tobramycin
Clinical data
Trade names	Nebcin, Tobrex, Tobi, others
Other names	47663, SPRC-AB01
AHFS/Drugs.com	Monograph
MedlinePlus	a682660
License data	US DailyMed: Tobramycin;
Pregnancy; category	AU: D;
Routes of; administration	Intravenous, intramuscular, inhalation, ophthalmic
ATC code	J01GB01 (WHO) S01AA12 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	Not bound
Metabolism	Not metabolized
Elimination half-life	2–3 hrs
Excretion	Exclusively via kidneys
Identifiers
	IUPAC name (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	32986-56-4 ;
PubChem CID	36294;
DrugBank	DB00684 ;
ChemSpider	33377 ;
UNII	VZ8RRZ51VK;
KEGG	D00063 ; C00397 ;
ChEBI	CHEBI:28864 ;
ChEMBL	ChEMBL1747 ;
PDB ligand	TOY (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8023680 ;
ECHA InfoCard	100.046.642
Chemical and physical data
Formula	C18H37N5O9
Molar mass	467.520 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI 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 ; Key:NLVFBUXFDBBNBW-PBSUHMDJSA-N ;
	(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.^[8]

It was patented in 1965, and approved for medical use in 1974.^[9] It is on the World Health Organization's List of Essential Medicines.^[10] In 2022, it was the 281st most commonly prescribed medication in the United States, with more than 600,000 prescriptions.^[11]^[12]

^ "Tobramycin Use During Pregnancy". Drugs.com. 11 November 2019. Retrieved 28 April 2020.
^ "Tobramycin ophthalmic Use During Pregnancy". Drugs.com. 24 December 2019. Retrieved 28 April 2020.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ "Tobramycin 40mg/mL Injection – Summary of Product Characteristics (SmPC)". (emc). 9 October 2018. Retrieved 28 April 2020.
^ "Tobi Podhaler EPAR". European Medicines Agency (EMA). 17 March 2003. Retrieved 10 August 2024.
^ Haberfeld H, ed. (2021). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Tobramycin B. Braun 1 mg/mL Infusionslösung.
^ "Tobramycin" (PDF). Toku-E. 12 January 2010. Retrieved 11 June 2012.
^ 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)
^ 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.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Tobramycin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[Drugs.com_pregnancy-1] "Tobramycin Use During Pregnancy". Drugs.com. 11 November 2019. Retrieved 28 April 2020.

[Drugs.com_pregnancy_ophthalmic-2] "Tobramycin ophthalmic Use During Pregnancy". Drugs.com. 24 December 2019. Retrieved 28 April 2020.

[3] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[4] "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.

[Tobramycin_SmPC-5] "Tobramycin 40mg/mL Injection – Summary of Product Characteristics (SmPC)". (emc). 9 October 2018. Retrieved 28 April 2020.

[6] "Tobi Podhaler EPAR". European Medicines Agency (EMA). 17 March 2003. Retrieved 10 August 2024.

[AC-7] Haberfeld H, ed. (2021). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Tobramycin B. Braun 1 mg/mL Infusionslösung.

[8] "Tobramycin" (PDF). Toku-E. 12 January 2010. Retrieved 11 June 2012.

[Fis2006-9] 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)

[WHO23rd-10] 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.

[Top_300_of_2022-11] "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.

[12] "Tobramycin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

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