Kanamycin A Sulfate

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Cat Number

API0232297

CAS Number

3847-27-6

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CAS Number

3847-27-6

EINECS

223-347-1

Storage

Store at 2-8°C

Synonyms

Kanamycin monosulfate; Kantrex; Kanamycin (sulfate); Kanamycin A monosulfate; DTXSID1047524; J80EX28SMQ

Molecular Formula

C18H38N4O15S

Molecular Weight

582.6

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.OS(=O)(=O)O

Appearance

White to off-white solid powder

Melting Point

250°C

Boiling Point

809.5°C at 760 mmHg

Relative Density

1.3619 (Estimate)

General Description

Kanamycin A sulfate is an aminoglycoside antibiotic produced by Streptomyces kanamyceticus, with a deoxystreptamine ring and two sugar moieties. Its chemical structure is a 2-deoxystreptamine derivative with kanosamine and kanamycin B. Kanamycin A is a white to off-white powder, soluble in water. It is a potent bactericidal agent with a broad spectrum of activity.

Mechanism of Action

Kanamycin binds to the 30S ribosomal subunit of susceptible bacteria, specifically to the 16S rRNA, interfering with the initiation complex and causing misreading of the genetic code. This leads to the production of abnormal proteins and the inhibition of protein synthesis, resulting in bacterial cell death. The drug is bactericidal and exhibits concentration-dependent activity.

Application

Kanamycin is indicated for the treatment of serious infections caused by gram-negative bacteria, including Escherichia coli, Klebsiella, and Proteus, and for the treatment of tuberculosis, particularly multidrug-resistant tuberculosis. It is also used for the treatment of infections caused by Staphylococcus species.

This study combined molecular docking, dynamics, fluorescence, ITC, and CD to characterize kanamycin binding to E. coli TolC. Binding induced concentration-dependent quenching with a 7‑nm blue shift and was endothermic, entropy-driven, with a single site. Secondary structure remained largely unchanged, but tertiary rearrangements occurred, supported by RMSD, Rg, and RMSF data. Hydrogen bonds and hydrophobic contacts stabilized the complex. The experimental and computational findings correlate well, revealing that kanamycin recognition by TolC may maintain an open conformation conducive to efflux, offering molecular-level insight into cross-resistance mechanisms and potential strategies to disrupt antibiotic export.

Fig. 1 Two-dimensional representation of TolC-kanamycin interaction complex analysis. (Pattanayak BS, et al., 2021)

References

Pattanayak BS, et al. Kanamycin-Mediated Conformational Dynamics of Escherichia coli Outer Membrane Protein TolC. Front Mol Biosci. 2021;8:636286.

Hydroxyapatite coatings embedded with kanamycin and fibroblast growth factor 2 were developed for bone implants. The coatings were cytocompatible, promoted osteoblast adhesion and spreading, and significantly inhibited bacterial biofilm formation for at least 2 days, especially against Gram‑positive pathogens. These multifunctional coatings may reduce device‑associated infections while improving osseointegration.

Fig. 2 IR maps assigned to the distribution of phosphate (a1,b1) and methylene (a2,b2) groups and IR spectra of dropcast (a3) and HAp/KAN/FGF2 (fibroblast growth factor 2) coatings obtained at 300 mJ/cm2 laser fluence (b3). (Gherasim O, et al., 2021)

References

Gherasim O, et al. Bioactive Coatings Based on Hydroxyapatite, Kanamycin, and Growth Factor for Biofilm Modulation. Antibiotics (Basel). 2021;10(2):160.

Does Kanamycin A Sulfate require refrigerated storage as an aminoglycoside antibiotic?

Yes, it must be stored at 2–8°C. At room temperature, degradation via hydrolysis of the glycosidic bonds and oxidation occurs.

Is Kanamycin A Sulfate sensitive to light and moisture during storage?

Yes, it is both photosensitive and hygroscopic. Store in original, tightly sealed, light‑resistant containers with desiccant under refrigeration.

What is the stability of Kanamycin A Sulfate after reconstitution for injectable use?

Reconstituted solutions are stable for up to 24 hours under refrigeration.

How is the impurity kanamycin B (a process‑related impurity) monitored?

This impurity is quantified using a stability‑indicating HPLC method with pulsed amperometric detection (PAD), ensuring it remains within pharmacopoeial limits.