General Information

Alafosfalin Impurities and Alafosfalin 

Daicel Pharma is a reliable partner for synthesizing high-quality Alafosfalin impurities, specifically ((S)-1-((S)-2-aminopropanamido)ethyl)phosphonic acid, (1-((S)-2-aminopropanamido)ethyl)phosphonic acid, benzyl ((2R)-1-((1-(dimethoxyphosphoryl)ethyl)amino)-1-oxopropan-2-yl)carbamate, benzyl ((2S)-1-((1-(dimethoxyphosphoryl)ethyl)amino)-1-oxopropan-2-yl)carbamate and L-Alanyl-L-1-aminoethylphosponic acid. These impurities help assess the quality, stability, and safety of the active pharmaceutical ingredient, Alafosfalin. Daicel Pharma also offers a custom synthesis of Alafosfalin impurities, which can be shipped worldwide to meet customers’ unique requirements.

Alafosfalin [CAS: 60668-24-8] is a phosphonodipeptide that inhibits bacterial cell wall biosynthesis. It is an antibacterial, effective against many organisms, particularly Gram-negative bacteria.

Alafosfalin: Use and Commercial Availability  

Alafosfalin is a well-known antibacterial agent synthesized by Roche. It has a broad spectrum of antibacterial activity against certain Gram-positive aerobes, anaerobic bacteria, and many species of Enterobacterales. It is highly effective against Escherichia coli and moderately effective against Serratia, Klebsiella, Enterobacter, and Citrobacter. It is bactericidal against Gram-negative bacteria, causing rapid lysis of susceptible strains.

Alafosfalin Structure and Mechanism of Action

The chemical name of Alafosfalin is (1R)-1-(L-Alanylamino)ethylphosphonic acid. Its chemical formula is C₅H₁₃N₂O₄P, and its molecular weight is approximately 196.14 g/mol.

Alafosfalin bacterial uptake is through LL-dipeptide permeases. Its subsequent hydrolysis yields fosfalin (L-1-aminoethylphosphonic acid). It binds with alanine racemase. Further, it prevents the synthesis of D-alanine, which is essential for peptidoglycan biosynthesis.

Alafosfalin Impurities and Synthesis

There is limited information available on the impurities of Alafosfalin, an antibiotic. However, impurities may form during the synthesis¹, storage, and handling of the organic compound. They can impact the efficacy and safety of the drug product. Thus, it is essential to control and minimize impurities during the manufacturing process and ensure appropriate storage conditions to maintain the quality of the drug product.

Daicel Pharma issues a Certificate of Analysis (CoA) for Alafosfalin impurity standards, including ((S)-1-((S)-2-aminopropanamido)ethyl)phosphonic acid, (1-((S)-2-aminopropanamido)ethyl)phosphonic acid, benzyl ((2R)-1-((1-(dimethoxyphosphoryl)ethyl)amino)-1-oxopropan-2-yl)carbamate, benzyl ((2S)-1-((1-(dimethoxyphosphoryl)ethyl)amino)-1-oxopropan-2-yl)carbamate and L-Alanyl-L-1aminoethylphosponic acid. The CoA is from an analytical facility that complies with current Good Manufacturing Practices (cGMP) and includes comprehensive characterization data, such as 1H NMR, 13C NMR, IR, MASS, and HPLC purity². We give additional characterization data such as 13C-DEPT and CHN on request. Daicel Pharma can prepare unknown Alafosfalin impurities or degradation products. A complete characterization report accompanies each delivery.