Tobramycin hydrochlorideProduct ingredient for Tobramycin

Name
Tobramycin hydrochloride
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

Accession Number
DBSALT002273
Structure
Synonyms
Not Available
UNII
01IX3OU168
CAS Number
95188-93-5
Weight
Average: 503.98
Monoisotopic: 503.2358055
Chemical Formula
C18H38ClN5O9
InChI Key
CVDADWBWFLWJNQ-TWDWGCDDSA-N
InChI
InChI=1S/C18H37N5O9.ClH/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;1H/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 hydrochloride
SMILES
Cl.NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O
ChemSpider
32697392
Predicted Properties
PropertyValueSource
Water Solubility53.7 mg/mLALOGPS
logP-3ALOGPS
logP-6.5Chemaxon
logS-0.94ALOGPS
pKa (Strongest Acidic)12.54Chemaxon
pKa (Strongest Basic)9.66Chemaxon
Physiological Charge5Chemaxon
Hydrogen Acceptor Count14Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area268.17 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity106.69 m3·mol-1Chemaxon
Polarizability46.74 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon