(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

• ChemBase ID: 566
• Molecular Formular: C18H37N5O9
• Molecular Mass: 467.51448
• Monoisotopic Mass: 467.25912779
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@H](O1)O[C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@H]1O[C@@H]([C@H](C[C@H]1N)O)CN)N)N)O)N)O)CO
• Canonical SMILES: NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@H]([C@@H]([C@H]2O)O[C@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)N)O)N)[C@@H](C[C@@H]1O)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
• InChIKey: NLVFBUXFDBBNBW-PBSUHMDJSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: tobramycin
• Brand Name: Aktob; Distobram; Gernebcin; NF 6; Nebcin; Nebramycin; Nebramycin 6; Nebramycin Factir 6; Nebramycin Factor 6; Nebramycin Vi; Obracin; Obramycin; Tenebrimycin; Tenemycin; Tobi; Tobracin; Tobradex; Tobradistin; Tobramaxin; Tobramitsetin; Tobramycetin; Tobrasone; Tobrex; Sybryx
• Synonyms: 3'-Deoxykanamycin B; Tobramycin Sulfate; tobramycin solution for inhalation; SPRC-AB01; Tobramycin

Database IDs

• CAS Number: 32986-56-4
• PubChem SID: 160964029; 46507662
• PubChem CID: 36294

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.542545
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -20.344318
• LogD (pH = 7.4): -13.627587
• Log P: -6.4775004
• Molar Refractivity: 106.6949 cm^3
• Polarizability: 45.42405 Å^3
• Polar Surface Area: 268.17 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.98
• LOG S: -0.94
• Solubility (Water): 5.37e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1E+003 mg/ml
• Hydrophobicity(logP): -5.8

DETAILS

DrugBank - DB00684

• Drug Groups: approved; investigational
• Description: An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the pseudomonas species. It is a 10% component of the antibiotic complex, nebramycin, produced by the same species. [PubChem]
• Indication: For the treatment of pseudomonas aeruginosa lung infections. Also being investigated for use in the treatment of sinus infections.
• Pharmacology: Tobramycin, an aminoglycoside antibiotic obtained from cultures of Streptomyces tenebrarius, is used in combination with other antibiotics to treat urinary tract infections, gynecologic infections, peritonitis, endocarditis, pneumonia, bacteremia and sepsis, respiratory infections including those associated with cystic fibrosis, osteomyelitis, and diabetic foot and other soft-tissue infections. It acts primarily by disrupting protein synthesis, leading to altered cell membrane permeability, progressive disruption of the cell envelope, and eventual cell death. Tobramycin has in vitro activity against a wide range of gram-negative organisms including Pseudomonas aeruginosa.
• Toxicity: LD₅₀=441mg/kg (s.c. in mice)
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: The bioavailability of tobramycin may vary because of individual differences in nebulizer performance and airway pathology.
• Half Life: The elimination half-life of tobramycin from serum is approximately 2 hours after intravenous (IV) administration.
• External Links: Wikipedia; RxList; Drugs.com