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
| 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 | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
|---|---|---|
| [Clinical studies of cochleotoxicosis due to viomycin and kanamycin during tuberculostatic treatment (a prophylactic attempt)]. | 1968 |
|
| [Biochemical studies on nephrotoxicity of kanamycin]. | 1971 Feb |
|
| Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation. | 1975 Dec |
|
| In vitro susceptibility of Mycobacterium avium complex to antibacterial agents. | 1987 Nov |
|
| 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 |
|
| 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 |
|
| Therapeutic efficacy of liposome-encapsulated kanamycin against Mycobacterium intracellulare infection induced in mice. | 1991 Sep |
|
| Temporal bone studies of the human peripheral vestibular system. Aminoglycoside ototoxicity. | 2000 May |
|
| Rapamycin and less immunosuppressive analogs are toxic to Candida albicans and Cryptococcus neoformans via FKBP12-dependent inhibition of TOR. | 2001 Nov |
|
| Bactericidal activities of commonly used antiseptics against multidrug-resistant mycobacterium tuberculosis. | 2002 |
|
| Antitubercular cassane furanoditerpenoids from the roots of Caesalpinia pulcherrima. | 2003 Aug |
|
| Reversible anosmia after amikacin therapy. | 2003 Dec |
|
| New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
|
| [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 |
|
| Kanamycin ototoxicity in glutamate transporter knockout mice. | 2005 Jun 3 |
|
| Selection of gonadotrophin surge attenuating factor phage antibodies by bioassay. | 2005 Sep 26 |
|
| Rac/Rho pathway regulates actin depolymerization induced by aminoglycoside antibiotics. | 2006 Jun |
|
| Prosurvival and proapoptotic intracellular signaling in rat spiral ganglion neurons in vivo after the loss of hair cells. | 2007 Aug 20 |
|
| Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids. | 2008 Feb |
|
| Ototoxic drugs: difference in sensitivity between mice and guinea pigs. | 2010 Mar 1 |
|
| 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 |
|
| Mitochondrial peroxiredoxin 3 regulates sensory cell survival in the cochlea. | 2013 |
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 14:57:44 GMT 2023
by
admin
on
Fri Dec 15 14:57:44 GMT 2023
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| Record UNII |
01N552709G
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| Record Status |
Validated (UNII)
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| Record Version |
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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 |
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ANHYDROUS->SOLVATE |
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PARENT -> IMPURITY |
Amount Not Specified.
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ACTIVE MOIETY |
