Bekanamycin
[CAS# 4696-76-8]

Identification

• Classification: API >> Antibiotics >> Aminoglycoside
• Name: Bekanamycin
• Synonyms: (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
• Molecular Formula: C₁₈H₃₇N₅O₁₀
• Molecular Weight: 483.51
• CAS Registry Number: 4696-76-8
• EC Number: 225-170-5
• 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)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.668, Calc.^*
• Boiling Point: 807.7±65.0 ºC (760 mmHg), Calc.^*
• Flash Point: 442.3±34.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Danger
• Hazard Statements: H303-H317-H334-H360
• Precautionary Statements: P201-P202-P260-P270-P272-P280-P285-P301+P312-P302+P352-P304+P341-P308+P313-P342+P311-P363-P403-P501

Discovory and Applicatios

Bekanamycin is an aminoglycoside antibiotic discovered in the mid-20th century during the golden era of antibiotic discovery. It was isolated from the fermentation broth of a soil actinomycete, Streptomyces kanamyceticus. Scientists identified its potent antibacterial properties against a wide range of Gram-negative and Gram-positive bacteria, marking it as a significant breakthrough in the treatment of bacterial infections. Its structure, consisting of a central deoxystreptamine ring linked to amino sugars, is characteristic of aminoglycosides, contributing to its effectiveness in inhibiting bacterial protein synthesis.

Bekanamycin is primarily used to treat severe bacterial infections caused by both Gram-negative and Gram-positive bacteria. It is effective against organisms that are resistant to other antibiotics, making it a valuable option in combating antibiotic-resistant strains. Its mechanism involves binding to the bacterial 30S ribosomal subunit, disrupting protein synthesis and leading to bacterial cell death.

In agriculture, Bekanamycin is utilized as a veterinary antibiotic to treat infections in livestock and poultry. Its broad-spectrum activity ensures the health and productivity of farm animals, reducing the economic impact of bacterial diseases. Additionally, it is sometimes used in plant agriculture to control bacterial pathogens affecting crops, thereby improving yield and quality.

Bekanamycin is employed in molecular biology laboratories as a selective agent in genetic experiments. It is used to maintain plasmid stability in bacterial cultures by selecting for bacteria that carry resistance genes, which are often introduced as part of genetic engineering protocols. This selective pressure ensures that only genetically modified organisms thrive, facilitating studies in gene function and expression.

In public health, Bekanamycin plays a role in controlling outbreaks of bacterial infections, particularly in settings where rapid and effective treatment is crucial. Its ability to act quickly and efficiently against a broad spectrum of bacteria makes it an essential component of emergency medical kits for disaster relief and outbreak response.

Bekanamycin is often used in combination with other antibiotics to enhance its effectiveness and broaden its antibacterial spectrum. This synergistic approach is particularly useful in treating complex infections and reducing the likelihood of developing resistance. For example, it can be combined with beta-lactam antibiotics to target different aspects of bacterial cell function, resulting in more comprehensive treatment.