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CAS 51736-77-7

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6′′-O-Carbamoyltobramycin

Description:
6′′-O-Carbamoyltobramycin is a semi-synthetic derivative of tobramycin, an aminoglycoside antibiotic primarily used to treat bacterial infections, particularly those caused by Pseudomonas aeruginosa. This compound features a carbamoyl group at the 6′′ position of the tobramycin structure, which enhances its pharmacological properties. It exhibits antibacterial activity by inhibiting protein synthesis in susceptible bacteria, binding to the 30S ribosomal subunit. The modification at the 6′′ position may improve its stability and efficacy against certain resistant strains. Like other aminoglycosides, it is generally administered parenterally due to poor oral bioavailability. The compound's solubility, stability, and spectrum of activity can vary based on its chemical structure, making it a subject of interest in medicinal chemistry for developing new antibiotics. Safety and toxicity profiles are important considerations, as aminoglycosides can have nephrotoxic and ototoxic effects. Overall, 6′′-O-Carbamoyltobramycin represents a significant advancement in antibiotic development aimed at combating resistant bacterial infections.
Formula:C19H38N6O10
InChI:InChI=1S/C19H38N6O10/c20-3-9-8(26)2-7(23)17(32-9)34-15-5(21)1-6(22)16(14(15)29)35-18-13(28)11(24)12(27)10(33-18)4-31-19(25)30/h5-18,26-29H,1-4,20-24H2,(H2,25,30)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
InChI key:InChIKey=YPPFEJHOHNPKLT-PBSUHMDJSA-N
SMILES:O([C@H]1O[C@H](COC(N)=O)[C@@H](O)[C@H](N)[C@H]1O)[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](CN)[C@@H](O)C[C@H]3N)[C@@H](N)C[C@H]2N
Synonyms:
  • O-3-Amino-6-O-(aminocarbonyl)-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,3,6-trideoxy-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-D-streptamine
  • D-Streptamine, O-3-amino-6-O-(aminocarbonyl)-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,3,6-trideoxy-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-
  • Nebramycin V'
  • 6′′-O-Carbamoyltobramycin
  • Nebramycin factor 5′
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