(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编号: 566
• 分子式: C18H37N5O9
• 平均质量: 467.51448
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: tobramycin
• 商标名: 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
• 别名: 3'-Deoxykanamycin B; Tobramycin Sulfate; tobramycin solution for inhalation; SPRC-AB01; Tobramycin

登记号

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

理论计算性质

JChem

• Acid pKa: 12.542545
• 质子受体: 14
• 质子供体: 10
• LogD (pH = 5.5): -20.344318
• LogD (pH = 7.4): -13.627587
• Log P: -6.4775004
• 摩尔折射率: 106.6949 cm^3
• 极化性: 45.42405 Å^3
• 极化表面积: 268.17 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -2.98
• LOG S: -0.94
• 溶解度: 5.37e+01 g/l

分子性质

理化性质

• 溶解度: 1E+003 mg/ml
• 疏水性(logP): -5.8

详细说明

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