Abstract
Amoxicillin (AMOX) metabolism in human liver microsomes was studied in vitro using liquid chromatography–mass spectrometry (LC/MS). Amoxicillin was incubated with human liver microsomes along with NADPH, and the reaction mixture was analyzed by LC/MS to obtain the specific metabolic profile of the studied antibiotic drug. Positive electrospray ionization was employed as the ionization source. An ACE C18-column (4.6 mm × 150 mm, 3 μm) was implemented with acetonitrile and water (+0.1 % formic acid) in isocratic mode as the mobile phase at the flow 0.4 mL min−1. The chemical structures of metabolites were proposed on the basis of the accurate mass measurement of the protonated molecule as well as their main product. Six phase I and one phase II metabolites were detected and structurally described. The metabolism of AMOX occurred via oxidation, hydroxylation and oxidative deamination, as well as through combination of these reactions. Compound M7, with glucuronic acid was also observed as phase II metabolite. Neither sulfate nor glutathione conjugates were detected. This study presents novel information about the chemical structure of the potential AMOX metabolites and provides vital data for further pharmacokinetic and in vivo metabolism studies.
Highlights
Modern medicine is facing growing difficulties in treatment of bacterial infections resulting from an increasing number of antibiotic-resistant bacterial strains
Amoxicillin shows bactericidal effect as it blocks the activity of enzymes involved in synthesis of the cell wall
The parent drug was incubated with human liver fractions to search for phase I metabolites
Summary
Modern medicine is facing growing difficulties in treatment of bacterial infections resulting from an increasing number of antibiotic-resistant bacterial strains. The cause of this problem is the excessive use or misuse of antibacterial medicines in the treatment of human infections, and in the food industry, veterinary medicine and agriculture. Amoxicillin, 6-{[amino(4-hydroxyphenyl) acetyl]amino}-3,3-dimethyl-7-oxo-4-thial-1-azabicyclo[3.2.0]heptanes-2-carboxylic acid, belongs to β-lactam antibiotics of penicillin group [2]. This antibiotic acts against Gram-positive and Gram-negative bacteria and is most effective against anaerobes [2,3,4]. The antibiotic is used to treat certain bacterial infections such as gonorrhea, bronchitis, infections of the skin or soft tissue and infections of the upper and lower respiratory tract [2, 4]
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