Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H36N4O11 |
| Molecular Weight | 484.4986 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]3(O[C@H]1[C@H](N)C[C@H](N)[C@@H](O[C@@]2([H])O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O)O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O
InChI
InChIKey=SBUJHOSQTJFQJX-NOAMYHISSA-N
InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1
| Molecular Formula | C18H36N4O11 |
| Molecular Weight | 484.4986 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Kanamycin A is aminoglycoside anti-bacterial agent. Active against many strains of Gram-negative bacteria and Gram-positive Staphylococcus aureus and epidermis. Some strains of Mycobacterium bacterium are sensitive. Most active in alkaline solution. It binds to bacterial ribosomes and reduces mRNA translation hence reduces protein biosynthesis. However, it also exhibits some toxic effects towards mammalian cells.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Studies on nephrotoxicity of combined administration of kanamycin and sodium alginate]. | 1970 Jun |
|
| [Biochemical studies on nephrotoxicity of kanamycin]. | 1971 Feb |
|
| Nephropathy, an underestimated complication of methicillin therapy. | 1974 Jun |
|
| The quantification of kanamycin ototoxicity in the rat using conditioned tone discrimination. | 1975 Dec |
|
| Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation. | 1975 Dec |
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| Further studies on effects of irrigation solutions on rat bladders. | 1976 Dec |
|
| Potentiation of neuromuscular weakness in infant botulism by aminoglycosides. | 1979 Dec |
|
| [Detection of auditory impairment in the offsprings caused by drug treatment of the dams]. | 1982 Dec |
|
| Reflex modification as a test for sensory function. | 1985 Nov-Dec |
|
| MIC as a quantitative measurement of the susceptibility of Mycobacterium avium strains to seven antituberculosis drugs. | 1988 Aug |
|
| [Experimental study of drug-induced acute renal failure. Recovery after renal impairment caused by the administration of low molecular weight dextran and kanamycin in water-deprived rats]. | 1988 Feb |
|
| [Bilateral deafness after intra-lumbar administration of kanamycin]. | 1988 Jul-Aug |
|
| Action of antituberculous and beta-lactam drugs (including imipenem) against extra- and intra-cellularly growing Mycobacterium avium-intracellulare. | 1988 Mar-Apr |
|
| Expression of glutamate receptors in the cochlea of the normal and kanamycin-deaf rats. | 2000 |
|
| Mutant prevention concentration as a measure of antibiotic potency: studies with clinical isolates of Mycobacterium tuberculosis. | 2000 Sep |
|
| Overexpression of copper/zinc-superoxide dismutase protects from kanamycin-induced hearing loss. | 2001 May-Jun |
|
| Bactericidal activities of commonly used antiseptics against multidrug-resistant mycobacterium tuberculosis. | 2002 |
|
| Protective effect of calcium channel blocker verapamil on morphological and functional state of hair cells of the organ of corti in experimental kanamycin-induced ototoxicity. | 2002 Apr |
|
| Hearing loss and nephrotoxicity in long-term aminoglycoside treatment in patients with tuberculosis. | 2002 Jul |
|
| Reversible anosmia after amikacin therapy. | 2003 Dec |
|
| Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice. | 2003 Jan |
|
| Improved neural representation of vowels in electric stimulation using desynchronizing pulse trains. | 2003 Oct |
|
| Desynchronization of electrically evoked auditory-nerve activity by high-frequency pulse trains of long duration. | 2003 Oct |
|
| New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
|
| Adeno-associated virus-mediated Bcl-xL prevents aminoglycoside-induced hearing loss in mice. | 2007 Jul 20 |
|
| Cochlear repair by transplantation of human cord blood CD133+ cells to nod-scid mice made deaf with kanamycin and noise. | 2008 |
|
| Direct drug application to the round window: a comparative study of ototoxicity in rats. | 2009 Nov |
|
| Ototoxic drugs: difference in sensitivity between mice and guinea pigs. | 2010 Mar 1 |
|
| Novel cathelicidin-derived antimicrobial peptides from Equus asinus. | 2010 May |
|
| Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. | 2010 Oct |
|
| Amyloid-like protein inclusions in tobacco transgenic plants. | 2010 Oct 26 |
|
| The multifunctional host defense peptide SPLUNC1 is critical for homeostasis of the mammalian upper airway. | 2010 Oct 7 |
|
| Dominant incidence of multidrug and extensively drug-resistant specific Mycobacterium tuberculosis clones in Osaka Prefecture, Japan. | 2012 |
|
| Mitochondrial peroxiredoxin 3 regulates sensory cell survival in the cochlea. | 2013 |
|
| Potent activity against multidrug-resistant Mycobacterium tuberculosis of α-mangostin analogs. | 2013 |
|
| Chlorinated coumarins from the polypore mushroom Fomitopsis officinalis and their activity against Mycobacterium tuberculosis. | 2013 Oct 25 |
Sample Use Guides
Rabbit reticulocyte ribosomes were used to investigate the activities of kanamycin A on higher eukaryotic ribosomes. The drug-mediated inhibition of
protein synthesis by determining IC50 values in translation of luciferase mRNA was assessed. The IC50 for Kanamycin A is 126.85 uM.
eukaryotic protein synthesis.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:59:37 GMT 2023
by
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on
Fri Dec 15 15:59:37 GMT 2023
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| Record UNII |
EQK9Q303C5
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| Record Status |
Validated (UNII)
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C2363
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SALT/SOLVATE -> PARENT |
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PARENT -> IMPURITY |
Amikacin is a semi-synthetic product derived from a fermentation product, kanamycin A. Amikacin contains not less than 96.5% and not more than 102.0% (Assay, Method A) or not less than 98.5% and not more than 101.0% (Assay, Method B) of amikacin (C22H43N5O13), calculated with reference to the anhydrous substance.
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PARENT -> IMPURITY |
Amikacin sulfate is a semi-synthetic product derived from a fermentation product, kanamycin A. Amikacin sulfate (1:2) contains not less than 96.5% and not more than 102.0% of amikacin sulfate (C22H43N5O13,2H2SO4), calculated with reference to the dried substance. Amikacin sulfate (1:1.8) contains not less than 96.5% and not more than 102.0% of amikacin sulfate (C22H43N5O13,1.8H2SO4), calculated with reference to the dried substance.
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ACTIVE MOIETY |
