Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H36N4O11.H2O4S |
| Molecular Weight | 582.577 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.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=OOYGSFOGFJDDHP-KMCOLRRFSA-N
InChI=1S/C18H36N4O11.H2O4S/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;1-5(2,3)4/h4-18,23-29H,1-3,19-22H2;(H2,1,2,3,4)/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 |
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Chlorinated coumarins from the polypore mushroom Fomitopsis officinalis and their activity against Mycobacterium tuberculosis. | 2013-10-25 |
|
| Mitochondrial peroxiredoxin 3 regulates sensory cell survival in the cochlea. | 2013 |
|
| Potent activity against multidrug-resistant Mycobacterium tuberculosis of α-mangostin analogs. | 2013 |
|
| Dominant incidence of multidrug and extensively drug-resistant specific Mycobacterium tuberculosis clones in Osaka Prefecture, Japan. | 2012 |
|
| Conservation of endocochlear potential in mice with profound hearing loss induced by co-administration of kanamycin and furosemide. | 2011-04 |
|
| Amyloid-like protein inclusions in tobacco transgenic plants. | 2010-10-26 |
|
| [Drug-induced nephropathy and hemorrhagic cystitis as an adverse reaction to kanamycin]. | 1989-08 |
|
| Comparison of bactericidal activities of streptomycin, amikacin, kanamycin, and capreomycin against Mycobacterium avium and M. tuberculosis. | 1989-08 |
|
| [Prevention of neurosensory hearing disorders in antibiotic-induced ototoxicosis]. | 1989-03-01 |
|
| [Acute renal failure caused by ceporin, kanamycin and gentamicin]. | 1989-03-01 |
|
| New antibiotics, resorcinomycins A and B: antibacterial activity of resorcinomycin A against mycobacteria in vitro. | 1989-03 |
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| 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 |
|
| MIC as a quantitative measurement of the susceptibility of Mycobacterium avium strains to seven antituberculosis drugs. | 1988-08 |
|
| [Bilateral deafness after intra-lumbar administration of kanamycin]. | 1988-07-01 |
|
| Qualitative and quantitative drug-susceptibility tests in mycobacteriology. | 1988-05 |
|
| Action of antituberculous and beta-lactam drugs (including imipenem) against extra- and intra-cellularly growing Mycobacterium avium-intracellulare. | 1988-03-01 |
|
| [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]. | 1988-02 |
|
| In vitro susceptibility of Mycobacterium avium complex to antibacterial agents. | 1987-11 |
|
| Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex. | 1987 |
|
| Mycobacterial plasmids: screening and possible relationship to antibiotic resistance in Mycobacterium avium/Mycobacterium intracellulare. | 1986 |
|
| [Measurement of an auditory impairment induced by aminoglycosides using a shuttle box method in newborn rats]. | 1985-12 |
|
| Reflex modification as a test for sensory function. | 1985-11-01 |
|
| Furosemide ototoxicity: clinical and experimental aspects. | 1985-09 |
|
| In vitro antituberculosis activity of a new antibacterial substance ofloxacin (DL8280). | 1985-03 |
|
| Nephrotoxic effects of aminoglycoside treatment on renal protein reabsorption and accumulation. | 1984 |
|
| [Detection of auditory impairment in the offsprings caused by drug treatment of the dams]. | 1982-12 |
|
| In vitro susceptibility of Mycobacterium avium complex and Mycobacterium tuberculosis strains to a spiro-piperidyl rifamycin. | 1982-09 |
|
| Potentiation of neuromuscular weakness in infant botulism by aminoglycosides. | 1979-12 |
|
| Quantitative relationships of the ototoxic interaction of kanamycin and ethacrynic acid. | 1979-05 |
|
| Auditory thresholds and kanamycin-induced hearing loss in the guinea pig assessed by a positive reinforcement procedure. | 1978-02 |
|
| [Amikacin and kanamycin. Comparative experimental studies on nephrotoxicity]. | 1978 |
|
| Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms. | 1977-03-12 |
|
| [On the mechanism of kanamycin ototoxicity (II): --Alteration of glucose metabolism in cochlea and kidney (author's transl)]. | 1977-01-20 |
|
| Proceedings: The use of conditioned tone discrimination to study kanamycin ototoxicity in the rat. | 1975-12 |
|
| The quantification of kanamycin ototoxicity in the rat using conditioned tone discrimination. | 1975-12 |
|
| Nephropathy, an underestimated complication of methicillin therapy. | 1974-06 |
|
| Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains. | 1973-09 |
|
| Laboratory testing for ototoxic effects of drugs. | 1973-06 |
|
| Acute renal failure in general surgical patients. | 1971-06 |
|
| [Biochemical studies on nephrotoxicity of kanamycin]. | 1971-02 |
|
| [Severe hearing disorders caused by kanamycin]. | 1970-09 |
|
| [Hearing damages in prolonged kanamycin therapy]. | 1970-08 |
|
| [Studies on nephrotoxicity of combined administration of kanamycin and sodium alginate]. | 1970-06 |
|
| Kanamycin ototoxicity--possible potentiation by other drugs. | 1970-05 |
|
| [Recovery after hemodialysis in 2 cases of acute renal insufficiency during treatment with kanamycin and colistin methanesulfonate]. | 1970-04-27 |
|
| [Clinical studies of cochleotoxicosis due to viomycin and kanamycin during tuberculostatic treatment (a prophylactic attempt)]. | 1968 |
|
| 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. | 1967-07 |
|
| Unusual neurotoxicity of kanamycin. | 1967-05-01 |
|
| Rifampicin: a new rifamycin. II. Laboratory studies on the antituberculous activity and preliminary clinical observations. | 1967-05 |
|
| [Clinical use of vitamin K-1 in hearing disorders caused by kanamycin]. | 1966-04 |
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
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Edited
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| Record UNII |
J80EX28SMQ
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Validated (UNII)
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C2363
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CFR |
21 CFR 522.1204
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ACTIVE MOIETY |
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