Tobramycin sulfateProduct ingredient for Tobramycin

Name

Tobramycin sulfate

Drug Entry

Tobramycin

Aminoglycosides, many of which are derived directly from Streptomyces spp., are concentration-dependent bactericidal antibiotics with a broad spectrum of activity against Gram-positive and Gram-negative organisms.¹ Inhaled tobramycin is notable for its use in treating chronic Pseudomonas aeruginosa infections in cystic fibrosis patients, as P. aeruginosa is notoriously inherently resistant to many antibiotics.^1,2,13 However, tobramycin can also be administered intravenously and topically to treat a variety of infections caused by susceptible bacteria.^14,15 Its use is limited in some cases by characteristic toxicities such as nephrotoxicity and ototoxicity, yet it remains a valuable option in the face of growing resistance to front-line antibiotics such as β-lactams and cephalosporins.^1,12,13,15

Tobramycin was approved by the FDA in 1975 and is currently available in a variety of forms for administration by inhalation, injection, and external application to the eye (ophthalmic).^13,14,15

See full entry for Tobramycin

Accession Number

DBSALT000317

Structure

Similar Structures

Synonyms

Not Available

UNII

HJT0RXD7JK

CAS Number

49842-07-1

Weight

Average: 565.593
Monoisotopic: 565.226507049

Chemical Formula

C₁₈H₃₉N₅O₁₃S

InChI Key

ZEUUPKVZFKBXPW-TWDWGCDDSA-N

InChI

InChI=1S/C18H37N5O9.H2O4S/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;1-5(2,3)4/h5-18,24-28H,1-4,19-23H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;/m0./s1

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; sulfuric acid

SMILES

OS(O)(=O)=O.[H][C@@]1(N)C[C@]([H])(O)[C@@]([H])(CN)O[C@]1([H])O[C@]1([H])[C@@]([H])(N)C[C@@]([H])(N)[C@]([H])(O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(N)[C@@]2([H])O)[C@@]1([H])O

External Links

PubChem Compound: 62005
ChemSpider: 55853
ChEBI: 774731
ChEMBL: CHEMBL1200780
Wikipedia: Tobramycin

Predicted Properties

Property	Value	Source
Water Solubility	53.7 mg/mL	ALOGPS
logP	-3	ALOGPS
logP	-6.5	Chemaxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	12.54	Chemaxon
pKa (Strongest Basic)	9.66	Chemaxon
Physiological Charge	5	Chemaxon
Hydrogen Acceptor Count	14	Chemaxon
Hydrogen Donor Count	10	Chemaxon
Polar Surface Area	268.17 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	106.69 m³·mol^-1	Chemaxon
Polarizability	47.11 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Tobramycin sulfateProduct ingredient for Tobramycin

Structure for Tobramycin sulfate (DBSALT000317)