Active Ingredient History

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Amikacin, USP (as the sulfate) is a semi-synthetic aminoglycoside antibiotic derived from kanamycin. Amikacin "irreversibly" binds to specific 30S-subunit proteins and 16S rRNA. Amikacin inhibits protein synthesis by binding to the 30S ribosomal subunit to prevent the formation of an initiation complex with messenger RNA. Specifically Amikacin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes. Amikacin is used for short-term treatment of serious infections due to susceptible strains of Gram-negative bacteria, including Pseudomonas species, Escherichia coli, species of indole-positive and indole-negative Proteus, Providencia species, Klebsiella-Enterobacter-Serratia species, and Acinetobacter (Mima-Herellea) species. Amikacin may also be used to treat Mycobacterium avium and Mycobacterium tuberculosis infections. Amikacin was used for the treatment of gram-negative pneumonia.   NCATS

  • SMILES: NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O
  • InChIKey: LKCWBDHBTVXHDL-RMDFUYIESA-N
  • Mol. Mass: 585.61
  • ALogP: -8.42
  • ChEMBL Molecules:
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Drug Pricing (per unit)

United States

$5.6450 - $279.5289
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Note: This drug pricing data is preliminary, incomplete, and may contain errors.

1-n-(l(-)-gamma-amino-alpha-hydroxybutyryl)kanamycin a | amicacin | amiglyde | amiglyde-v | amikacillin | amikacin | amikacina | amikacine | amikacin hydrate | amikacin sulfate | amikacin sulphate | amikacinum | amikavet | amikin | arikace | bb-k8 | briclin | liposomal amikacin | lukadin | o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1->4)-o-(6-amino-6-deoxy-alpha-d-glucopyranosyl-(1->6))-n(3)-(4-amino-l-2-hydroxybutyryl)-2-deoxy-l-streptamine

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