Kasugamycin hydrochloride Chemical Properties

Melting point:

202-204 °C (decomp)

vapor pressure 

<1.3x l0^-8 Pa (25 °C)

storage temp. 

Sealed in dry,2-8°C

solubility 

H₂O: soluble

pka

3.23 (carboxyl), 7.73 and 11.0 (bases)

Water Solubility 

125 g l^-1 (25 °C)

form 

Solid

color 

white to off-white

Stability:

Hygroscopic

CAS DataBase Reference

19408-46-9(CAS DataBase Reference)

EPA Substance Registry System

Kasugamycin monohydrochloride (19408-46-9)

Safety Information

Safety Statements 

22-24/25-26

WGK Germany 

2

RTECS 

NM7521800

Kasugamycin hydrochloride Usage And Synthesis

Description

Kasugamycin is an aminoglycosidic antibiotic isolated from S. kasugaensis. It blocks the initiation of translation, preventing initiation complex formation on 30S ribosomes in bacteria.

Uses

antifungal

Uses

kasugamycin, derived from Streptomyces kasuguensis, is also used to control rice blast.It acts by inhibiting protein synthesis by interfering with the binding of aminoacyl-tRNA to the mRNA-30s ribosomal subunit complex (Yamaguchi, 1998).

Uses

Kasugamycin Hydrochloride is an aminoglycoside antibiotic that inhibits the initiation of translation. It is also a type of fungicide that controls leaf and neck blast disease caused by Pyricularia oryzae and increases rice yields.

in vitro

kasugamycin could inhibit protein synthesis by interacting with the 30s ribosomal subunit. the mechanism of inhibition of protein synthesis appeared to be different from that of other aminoglycosides, such as kanamycin, streptomycin, neomycin, gentamicin. the initiation complex formation on 30s ribosomes could be inhibited by kasugamycin but not by streptomycin, kanamycin or gentamicin, though the binding of fmet-trna to 70s ribosomes was inhibited by both streptomycin and by kasugamycin. [1].

in vivo

five groups, each consisting of five guinea pigs, were infected with shibaura strain; two groups were treated by injection with kasugamycin. all animals treated with 1 mcg/g were killed showing an average survival period of 7.4 days, which was close to the average survival period of 6.2 days in the control group; while all animals treated with 5 mcg/g survived. the other two groups were treated with kasugamycin from the icteric stage to the 10th day after infection. two animals of the 5 mcg/g group survived, showing no leptospira in the kidney; the other three died in an average of 7.7 days. three animals of the 10 mcg/g group survived; while the other two animals died in 6.5 days on an average . the total amounts of kasugamycin administered to the infected guinea pigs from the febrile stage were 10.8 mg (the 1 mcg/g group) and 54.0 mg (the 5 mcg/g group) [2].

Metabolic pathway

kasugamycin hydrochloride hydrate is a relatively stable antibiotic. There is limited published information on its metabolism and environmental fate but it is extensively degraded in plants and soil as indicated in Scheme 1.

Degradation

kasugamycin hydrochloride hydrate is very stable at room temperature. It is stable in weak acids but unstable in strong acids and under basic conditions. Its DT₅₀ values at 50 °C are 47 and 14 days at pH 5 and 9, respectively (PM).

References

[1] okuyama, a. ,machiyama, n.,kinoshita, t., et al. inhibition by kasugamycin of initiation complex formation on 30s ribosomes. biochemical and biophysical research communications 43(1), 196-199 (1971).
[2] kitaoka m, mori m, arimitsu y. in vitro and in vivo effects of kasugamycin on leptospira icterohaemorrhagiae. jpn j med sci biol. 1975 oct-dec;28(5-6):285-90.

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