Kanamycin

Base Information

• Chemical Name: Kanamycin
• CAS No.: 59-01-8
• Deprecated CAS: 11025-65-3,19079-03-9,64013-69-0,936337-76-7,717087-69-9,1807443-02-2,19079-03-9,64013-69-0,936337-76-7
• Molecular Formula: C18H36 N4 O11
• Molecular Weight: 484.504
• European Community (EC) Number: 200-411-7,232-512-7,684-844-0
• UNII: EQK9Q303C5
• DSSTox Substance ID: DTXSID3023184
• Nikkaji Number: J4.492J
• Wikipedia: Kanamycin_A
• Wikidata: Q27094615
• NCI Thesaurus Code: C65997,C65998,C76151,C76152
• RXCUI: 6099
• Metabolomics Workbench ID: 43390
• ChEMBL ID: CHEMBL1384
• Mol file: 59-01-8.mol

Synonyms:Kanamycin;Kanamycin A;Kanamycin Sulfate;Kantrex

Chemical Property of Kanamycin

Chemical Property:

• Vapor Pressure: 2.47E-30mmHg at 25°C
• Refractive Index: 1.669
• Boiling Point: 809.5°Cat760mmHg
• PKA: pKa 6.40/7.55/8.40/9.40(H2O) (Uncertain)
• Flash Point: 443.4°C
• PSA: 282.61000
• Density: 1.62g/cm³
• LogP: -4.49020
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: -6.9
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 484.23805798
• Heavy Atom Count: 33
• Complexity: 638

Purity/Quality:

99% ^*data from raw suppliers

Kanamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)O)O)OC3C(C(C(C(O3)CO)O)N)O)N
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N
• Recent ClinicalTrials: The Evaluation of a Standard Treatment Regimen of Anti-tuberculosis Drugs for Patients With MDR-TB
• Recent NIPH Clinical Trials: Preoperative less painful mechanical bowel preparation in elective resection colorectal cancer surgery: a multicenter randomized non-Inferiority study
• Description: Kanamycin is a well-known bactericidal antibiotic. It belongs to the aminoglycoside antibiotic group. It can be used for the treatment of various pathogens including E. coli, Proteus species (both indole-positive and indole-negative), Enterobacter aerogenes, Klebsiella pneumoniae, Serratia marcescens and Acinetobacter species1-4. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate5. Aminoglycoside-type drug take actions through “irreversibly” binding to the 30S subunit of the ribosome, further blocking the protein synthesis. Kanamycin kills bacteria cells binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes5.
• Uses: Kanamycin A is an antibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil. Comprised of three components, kanamycin A, the major component, and kanamycins B and C, two minor congeners. Antibacterial.
• Indications: Kanamycin, O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-deoxy- 6-amino-α-D-glucopyranosyl-(1→4)]–2-deoxy-D-streptamine (32.4.6), is isolated from a culture fluid of the actinomycete Streptomyces kanamyceticus, which produces three antibiotics—kanamycins A, B, and C.Kanamycin A is similar to streptomycin and neomycines, and it possesses a broad spectrum of antimicrobial action. It is active with respect to most Gram-positive and Gramnegative microorganisms (staphylococci, colon bacillus, klebisella, Fridlender’s bacillus, proteus, shigella, salmonella).It is used to treat sepsis, meningitis, osteomyelitis, peritonitis, pneumonia, pyelonephritis, pyelocystitis, infected wounds, and post-operational, purulent complications that are caused by microorganisms sensitive to this drug. Kanamycin is used to treat tuberculosis of the lungs and other organs upon resistance to other antituberculosis drugs. Synonyms of this drug are karmycin, kamaxin, resistomycin, and many others.
• Clinical Use: Formerly used for severe infection with susceptible organisms, it has largely been superseded by other aminoglycosides.

Technology Process of Kanamycin

There total 13 articles about Kanamycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

Kanamycin A sulfate (3847-27-6,25389-94-0,64013-70-3,81129-79-5,84278-20-6,94108-19-7,94237-36-2,133-92-6) → kanamycin A (59-01-8)

Guidance literature:

With Amberlite IRA-400-OH; In water;

Reference yield: 83.0%

C34H46N4O16 → kanamycin A (59-01-8) + 1-deamino-1-dehydro-1-hydroxyiminokanamycin A

Guidance literature:

With hydrogen; acetic acid; palladium; In water; for 2h; under 760 Torr; Ambient temperature;

DOI:10.1246/bcsj.56.1807

Reference yield:

C22H43N5O13*2H2O4S → kanamycin A (59-01-8)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 20h; Reagent/catalyst; Solvent; Temperature;

upstream raw materials:

6'-N-hydroxykanamicyn A (sulfate)

di-tert-butyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,4S,5S,6R)-6-(((tert-butoxycarbonyl)amino)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate

3,6'-bis(N-benzyloxycarbonyl)-3-N-(trifluoroacetyl)kanamycin A

Kanamycin A sulfate

Downstream raw materials:

tetra-N-hepta-O-acetylkanamycin A

1,3,6',2''-tetra-N-benzyloxycarbonyl-kanamycin A

3,6'-di-N-p-methoxybenzyloxycarbonyl kanamycin A

kanamycin A 3'-phosphate

Refernces

• 1、 -. "Method for recovering kanamycin A from amikacin synthesis solution". Paragraph 0055-0060; 0066-0071; 0078-0083; 0090-0095; 0101. . Retrieved 2019/01/23.
• 2、 -. "COMPOUNDS AND METHODS OF TREATING RNA-MEDIATED DISEASES". Paragraph 00350; 00351. . Retrieved 2017/12/27.