Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H36N4O11.H2O.H2O4S |
| Molecular Weight | 600.592 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OS(O)(=O)=O.[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=VWSPLXPERFFCLK-KNQICTBBSA-N
InChI=1S/C18H36N4O11.H2O4S.H2O/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);1H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-;;/m1../s1
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 |
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| 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 |
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| Rifampicin: a new rifamycin. II. Laboratory studies on the antituberculous activity and preliminary clinical observations. | 1967 May |
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| Unusual neurotoxicity of kanamycin. | 1967 May 1 |
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| [Clinical studies of cochleotoxicosis due to viomycin and kanamycin during tuberculostatic treatment (a prophylactic attempt)]. | 1968 |
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| [Recovery after hemodialysis in 2 cases of acute renal insufficiency during treatment with kanamycin and colistin methanesulfonate]. | 1970 Apr 27 |
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| [Hearing damages in prolonged kanamycin therapy]. | 1970 Aug |
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| [Studies on nephrotoxicity of combined administration of kanamycin and sodium alginate]. | 1970 Jun |
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| Kanamycin ototoxicity--possible potentiation by other drugs. | 1970 May |
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| [Biochemical studies on nephrotoxicity of kanamycin]. | 1971 Feb |
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| Acute renal failure in general surgical patients. | 1971 Jun |
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| Laboratory testing for ototoxic effects of drugs. | 1973 Jun |
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| Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains. | 1973 Sep |
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| Nephropathy, an underestimated complication of methicillin therapy. | 1974 Jun |
|
| Proceedings: The use of conditioned tone discrimination to study kanamycin ototoxicity in the rat. | 1975 Dec |
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| The quantification of kanamycin ototoxicity in the rat using conditioned tone discrimination. | 1975 Dec |
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| Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms. | 1977 Mar 12 |
|
| Auditory thresholds and kanamycin-induced hearing loss in the guinea pig assessed by a positive reinforcement procedure. | 1978 Feb |
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| 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 |
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| 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 |
|
| [Measurement of an auditory impairment induced by aminoglycosides using a shuttle box method in newborn rats]. | 1985 Dec |
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| In vitro antituberculosis activity of a new antibacterial substance ofloxacin (DL8280). | 1985 Mar |
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| Reflex modification as a test for sensory function. | 1985 Nov-Dec |
|
| Furosemide ototoxicity: clinical and experimental aspects. | 1985 Sep |
|
| Mycobacterial plasmids: screening and possible relationship to antibiotic resistance in Mycobacterium avium/Mycobacterium intracellulare. | 1986 |
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| Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex. | 1987 |
|
| In vitro susceptibility of Mycobacterium avium complex to antibacterial agents. | 1987 Nov |
|
| 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 |
|
| 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 |
|
| [Drug-induced nephropathy and hemorrhagic cystitis as an adverse reaction to kanamycin]. | 1989 Aug |
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| Comparison of bactericidal activities of streptomycin, amikacin, kanamycin, and capreomycin against Mycobacterium avium and M. tuberculosis. | 1989 Aug |
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| New antibiotics, resorcinomycins A and B: antibacterial activity of resorcinomycin A against mycobacteria in vitro. | 1989 Mar |
|
| [Prevention of neurosensory hearing disorders in antibiotic-induced ototoxicosis]. | 1989 Mar-Apr |
|
| [Acute renal failure caused by ceporin, kanamycin and gentamicin]. | 1989 Mar-Apr |
|
| 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 |
|
| Conservation of endocochlear potential in mice with profound hearing loss induced by co-administration of kanamycin and furosemide. | 2011 Apr |
|
| 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.
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01N552709G
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56841873
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KANAMYCIN A SULFATE MONOHYDRATE
Created by
admin on Fri Dec 15 14:57:45 GMT 2023 , Edited by admin on Fri Dec 15 14:57:45 GMT 2023
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PRIMARY | Description: White or almost white, crystalline powder. Solubility: Freely soluble in water, practically insoluble in acetone R or ethanol (~750 g/l) TS. Category: Antibacterial. Storage: Kanamycin monosulfate should be kept in a tightly closed container, or if sterile, in a hermetically closed container. Labeling: The label states; - the content in terms of IU per mg, calculated with reference to the dried substance, - where applicable, that the substances is free from bacterial endotoxins, - where applicable, that the substance is sterile. Definition: Kanamycin monosulfate is produced by the growth of certain strains of Streptomyces kanamyceticus. Kanamycin monosulfate contains not less than 750 International Units per mg, with reference to the dried substance. | ||
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DTXSID20208329
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58207-20-8
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5965-95-7
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1413-65-6
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SUPERSEDED |
ACTIVE MOIETY
SUBSTANCE RECORD
