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Bekanamycin

Product Name
Bekanamycin
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
Formula Weight
483.51
MOL File
4696-76-8.mol
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Bekanamycin Property

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
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Safety

Toxicity
LD50 i.v. in mice: 136 mg/kg (Wakazawa)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
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N-Bromosuccinimide Price

TRC
Product number
K137523
Product name
KanamycinB
Packaging
250mg
Price
$165
Updated
2021/12/16
TRC
Product number
K137523
Product name
KanamycinB
Packaging
500mg
Price
$260
Updated
2021/12/16
Usbiological
Product number
257329
Product name
Kanamycin B
Packaging
1g
Price
$410
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0003070
Product name
KANAMYCIN B
Purity
95.00%
Packaging
100MG
Price
$583.82
Updated
2021/12/16
AK Scientific
Product number
J10862
Product name
KanamycinB
Packaging
5g
Price
$690
Updated
2021/12/16
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Bekanamycin Chemical Properties,Usage,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.

Originator

Kanendomycin,Meiji Seika,Japan,1969

Uses

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

Definition

ChEBI: Kanamycin B is a member of kanamycins. It is a conjugate base of a kanamycin B(5+).

Manufacturing Process

200 liters of the medium containing 2.0% starch, 1.0% soybean meal, 0.05% KCl, 0.05% MgSO4·7H2O, 0.3% NaCl, 0.2% NaNO3 was placed in the 400 liter fermenter, the pH was adjusted to 7.5, and the medium was then sterilized (pH after the sterilization was 7.0) for 30 minutes at 120°C, inoculated with 1,000 ml of 40 hour shake-cultured broth of S. kanamyceticus (a selected subculture of K2-J strain) and tank-cultured at 27°-29°C. As antifoam,soybean oil (0.04%)and silicone (0.04%) were added. The broth after 48 hours was found to contain 250 mcg/ml of kanamycin.
A portion (950 ml) of the rich eluate was adjusted to pH 6.0 by the addition of sulfuric acid. Ultrawet K (7.0 g) in 70 ml water was added slowly to the neutralized eluate to precipitate kanamycin B dodecylbenzenesulfonate which was collected by filtration after adding filter aid (Dicalite). The cake was washed with water and extracted with 100 ml methanol. After filtering and washing with methanol, sulfuric acid was added to the filtrate until no more kanamycin B sulfate precipitated. After addition of an equal volume of acetone to provide more complete precipitation, the kanamycin B sulfate was collected by filtration, washed with methanol and dried in vacuo at 50°C.

Therapeutic Function

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 sulfate (1:1)

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

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Bekanamycin Suppliers

Pharmaffiliates Analytics and Synthetics P. Ltd
Tel
--
Fax
--
Email
mktg@pharmaffiliates.com
Country
India
ProdList
6739
Advantage
58
SynZeal Research Pvt Ltd
Tel
--
Fax
--
Email
standards@synzeal.com
Country
India
ProdList
6514
Advantage
58
A.J Chemicals
Tel
--
Fax
--
Email
sales@ajchem.in
Country
India
ProdList
6100
Advantage
58
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View Lastest Price from Bekanamycin manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Bekanamycin 4696-76-8
Price
US $1.00-22.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100000KG
Release date
2024-08-07
Career Henan Chemical Co
Product
Bekanamycin 4696-76-8
Price
US $1.00/KG
Min. Order
1G
Purity
98%
Supply Ability
100KG
Release date
2018-08-20

4696-76-8, BekanamycinRelated Search:


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  • kanendomycin
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  • 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
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  • NK-1006
  • KANAMYCIN B
  • Kanamycin b (intermediates)
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  • aminodeoxykanamycin
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  • 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
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  • 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