Беканамицин

Описание

Bekanamycin, kanamycin B, was found in the culture broth of Streptomyces kanamyceticus by Umezawa et al. in 1957. It shows the same antibacterial spectrum as kanamycin but with stronger activity. The total synthesis of bekanamycin was completed by Umezawa et al. in 1968 and the knowledge gained from its synthesis was successfully applied to the synthesis of dibekacin.

Использование

Kanamycin B (cas# 4696-76-8) is a compound useful in organic synthesis.

Антимикробная активность

A component of the mixture of kanamycins produced by Streptomyces kanamyceticus. It is approximately twice as active as kanamycin A and is twice as toxic. It is not active against amikacin-resistant strains of MRSA. It is poorly active against Ps. aeruginosa.
The pharmacokinetics and uses are similar to those of kanamycin. A 0.5% ophthalmic solution has been used to treat gonococcal ophthalmia neonatorum. It is available in Japan.

Профиль безопасности

Poison by intravenous route.Moderately toxic by intraperitoneal and subcutaneousroutes. When heated to decomposition it emits toxicfumes of NOx.

Методы очистки

A small quantity of kanamycin B (24mg) can be purified on a small Dowex-1 x 2 column (6 x 50mm); the required fraction is evaporated to dryness and the residue crystallised from EtOH containing a small amount of H2O. [Umezawa et al. Bull Chem Soc Jpn 42 537 1969.] It has been crystallised from H2O by dissolving ~1g in H2O (3mL), adding Me2NCHO (3mL) and setting aside at 4o overnight. The needles are collected and dried to constant weight at 130o. It has also been recrystallised from aqueous EtOH. It is slightly soluble in CHCl3 and isoPrOH. [IR: Wakazawa et al. J Antibiot 14A 180, 187 1961, Ito et al. J Antibiot 17 A 189 1964, Beilstein 18 III/IV 7631.]