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Bekanamycin

Bekanamycin Structure
CAS No.
4696-76-8
Chemical Name:
Bekanamycin
Synonyms
kdm;NK-1006;NK 1006;KANAMYCIN B;Bekanamycin;nebramycinv;kanendomycin;Kanamycine B;Kanamycin B base;nebramycinfactor5
CBNumber:
CB7432846
Molecular Formula:
C18H37N5O10
Molecular Weight:
483.51
MOL File:
4696-76-8.mol
MSDS File:
SDS
Modify Date:
2024/8/7 19:09:42

Bekanamycin Properties

Melting point 178-182° (dec)
alpha D18 +130° (c = 0.5 in water); D21 +114° (c = 0.98 in water)
Boiling point 580.49°C (rough estimate)
Density 1.3771 (rough estimate)
refractive index 1.7600 (estimate)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
solubility Aqueous Acid (Slightly), Methanol (Slightly, Heated, Sonicated)
form Solid
pka 13.07±0.70(Predicted)
color Crystals
Stability Hygroscopic

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315; H319; H335
Precautionary statements  P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501
Toxicity LD50 i.v. in mice: 136 mg/kg (Wakazawa)
NFPA 704
0
2 0

Bekanamycin Chemical Properties,Uses,Production

Description

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.

Uses

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

Antimicrobial activity

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.

Safety Profile

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

Purification Methods

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.]

Bekanamycin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 141)Suppliers
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Orgamine Chemicals(I) Pvt Ltd +91-9820080281 +91-9820080281 Maharashtra, India 451 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
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Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6773 58 Inquiry
SynZeal Research Pvt Ltd +1 226-802-2078 Gujarat, India 6522 58 Inquiry
Shaanxi Dideu Medichem Co. Ltd 18192627656 China 3002 58 Inquiry
career henan chemical co +86-0371-86658258 +8613203830695 China 29899 58 Inquiry
Chongqing Chemdad Co., Ltd +86-023-6139-8061 +86-86-13650506873 China 39916 58 Inquiry
CONIER CHEM AND PHARMA LIMITED +8618523575427 China 49403 58 Inquiry
Hefei TNJ Chemical Industry Co.,Ltd. +86-0551-65418671 +8618949823763 China 34571 58 Inquiry
d-streptamine,o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(2,6-diamino-2, kanendomycin kdm nebramycinfactor5 nebramycinv (2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4-diol Bekanamycin NK 1006 NK-1006 KANAMYCIN B Kanamycin b (intermediates) 2’-amino-2’-deoxykanamycin aminodeoxykanamycin O-3-AMINO-3-DEOXY-D-GLUCOPYRANOSYL-(1,AT THE RATE4)-O-(2,6-DIAMINO-2,3,6TRIDEOXY-D-PER kanamycin/kanamycin sulfate Bekanamycin, >98% D-Streptamine, O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy- Tobramycin Impurity 1 (Tobramycin EP Impurity A) (Kanamycin B) (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-(((1R,2S,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol Bekanamycin USP/EP/BP Kanamycin Impurity B Kanamycin B base Tobramycin EP Impurity A Kanamycine B Kanamycin Impurity 3 4-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-6-O-(2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl)-L-streptamine (kanamycin B) Kanamycin B, EvoPure? 4696-76-8 C18H37N5O10 Inhibitors Pharmaceutical Intermediates API