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
NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
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 |
|---|---|---|
| [Clinical use of vitamin K-1 in hearing disorders caused by kanamycin]. | 1966 Apr |
|
| Experimental studies on therapeutic effects of various combinations of antituberculosis drugs. II. Comparison of various regimens in treatment of experimental mouse tuberculosis infected with SM- and INH-resistant Schacht strain. | 1967 Jul |
|
| Unusual neurotoxicity of kanamycin. | 1967 May 1 |
|
| [Clinical studies of cochleotoxicosis due to viomycin and kanamycin during tuberculostatic treatment (a prophylactic attempt)]. | 1968 |
|
| [Recovery after hemodialysis in 2 cases of acute renal insufficiency during treatment with kanamycin and colistin methanesulfonate]. | 1970 Apr 27 |
|
| [Hearing damages in prolonged kanamycin therapy]. | 1970 Aug |
|
| [Studies on nephrotoxicity of combined administration of kanamycin and sodium alginate]. | 1970 Jun |
|
| Kanamycin ototoxicity--possible potentiation by other drugs. | 1970 May |
|
| [Severe hearing disorders caused by kanamycin]. | 1970 Sep |
|
| [Biochemical studies on nephrotoxicity of kanamycin]. | 1971 Feb |
|
| Acute renal failure in general surgical patients. | 1971 Jun |
|
| Laboratory testing for ototoxic effects of drugs. | 1973 Jun |
|
| Nephropathy, an underestimated complication of methicillin therapy. | 1974 Jun |
|
| The quantification of kanamycin ototoxicity in the rat using conditioned tone discrimination. | 1975 Dec |
|
| [On the mechanism of kanamycin ototoxicity (II): --Alteration of glucose metabolism in cochlea and kidney (author's transl)]. | 1977 Jan 20 |
|
| Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms. | 1977 Mar 12 |
|
| [Amikacin and kanamycin. Comparative experimental studies on nephrotoxicity]. | 1978 |
|
| Auditory thresholds and kanamycin-induced hearing loss in the guinea pig assessed by a positive reinforcement procedure. | 1978 Feb |
|
| Potentiation of neuromuscular weakness in infant botulism by aminoglycosides. | 1979 Dec |
|
| Quantitative relationships of the ototoxic interaction of kanamycin and ethacrynic acid. | 1979 May |
|
| [Detection of auditory impairment in the offsprings caused by drug treatment of the dams]. | 1982 Dec |
|
| In vitro susceptibility of Mycobacterium avium complex and Mycobacterium tuberculosis strains to a spiro-piperidyl rifamycin. | 1982 Sep |
|
| Nephrotoxic effects of aminoglycoside treatment on renal protein reabsorption and accumulation. | 1984 |
|
| In vitro antituberculosis activity of a new antibacterial substance ofloxacin (DL8280). | 1985 Mar |
|
| MIC as a quantitative measurement of the susceptibility of Mycobacterium avium strains to seven antituberculosis drugs. | 1988 Aug |
|
| [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 |
|
| Qualitative and quantitative drug-susceptibility tests in mycobacteriology. | 1988 May |
|
| Nephrotoxicity of dactimicin, a novel pseudo-disaccharide aminoglycoside possessing the N-formimidoyl group, compared with that of astromicin, amikacin and other aminoglycoside antibiotics in animals. | 1989 |
|
| Comparison of bactericidal activities of streptomycin, amikacin, kanamycin, and capreomycin against Mycobacterium avium and M. tuberculosis. | 1989 Aug |
|
| New antibiotics, resorcinomycins A and B: antibacterial activity of resorcinomycin A against mycobacteria in vitro. | 1989 Mar |
|
| [Acute renal failure caused by ceporin, kanamycin and gentamicin]. | 1989 Mar-Apr |
|
| Therapeutic efficacy of liposome-encapsulated kanamycin against Mycobacterium intracellulare infection induced in mice. | 1991 Sep |
|
| Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs? | 1992 Dec |
|
| Mutant prevention concentration as a measure of antibiotic potency: studies with clinical isolates of Mycobacterium tuberculosis. | 2000 Sep |
|
| Kanamycin susceptibility testing of Mycobacterium tuberculosis using Mycobacterium Growth Indicator Tube and a colorimetric method. | 2001 Jun |
|
| Overexpression of copper/zinc-superoxide dismutase protects from kanamycin-induced hearing loss. | 2001 May-Jun |
|
| Reversible anosmia after amikacin therapy. | 2003 Dec |
|
| Improved neural representation of vowels in electric stimulation using desynchronizing pulse trains. | 2003 Oct |
|
| [The relationship between the fragment deletion of mtDNA in old rat and the sensitivity to aminoglycoside antibiotic induced deafness]. | 2004 Nov |
|
| Molecular analysis of cross-resistance to capreomycin, kanamycin, amikacin, and viomycin in Mycobacterium tuberculosis. | 2005 Aug |
|
| Selection of gonadotrophin surge attenuating factor phage antibodies by bioassay. | 2005 Sep 26 |
|
| Cochlear repair by transplantation of human cord blood CD133+ cells to nod-scid mice made deaf with kanamycin and noise. | 2008 |
|
| Deafferentation-associated changes in afferent and efferent processes in the guinea pig cochlea and afferent regeneration with chronic intrascalar brain-derived neurotrophic factor and acidic fibroblast growth factor. | 2008 Apr 1 |
|
| Limited functional conservation of a global regulator among related bacterial genera: Lrp in Escherichia, Proteus and Vibrio. | 2008 Apr 11 |
|
| Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids. | 2008 Feb |
|
| [A case of multi-drug resistant tuberculosis showing psychiatric adverse effect by cycloserine]. | 2008 Jan |
|
| A plasmacytoid dendritic cell (CD123+/CD11c-) based assay system to predict contact allergenicity of chemicals. | 2009 Oct 1 |
|
| Ototoxic drugs: difference in sensitivity between mice and guinea pigs. | 2010 Mar 1 |
|
| 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
Mon Mar 31 18:15:40 GMT 2025
by
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on
Mon Mar 31 18:15:40 GMT 2025
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| Record UNII |
EQK9Q303C5
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| Record Status |
Validated (UNII)
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| Record Version |
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C2363
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m6599
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C76151
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