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	UK: POM (Prescription only); US: WARNINGRx-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 ;
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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.

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

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