White or almost white, very hygroscopic, powder.
Antibiotic[Note—Amoxicillin sodium
will be used in combination with clavulanate potassium
and marketed as ‘‘Augmentin for intravenous administration’’].
ChEBI: Amoxicillin sodium is an organic sodium salt that is the monosodium salt of amoxicillin. It contains an amoxicillin(1-).
Amoxicillin is both a topical and a systemic sensitizer.
Topical sensitization occurs in health care workers.
Systemic drug reactions are frequent, such as urticaria,
maculo-papular rashes, baboon syndrome, acute generalized
exanthematous pustulosis, or even toxic epidermal
necrosis. Cross-reactivity is common with
ampicillin, and can occur with other penicillins.
Synthesis of (2S,5R,6R)-6-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid as sodium salt. 7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid in the following general steps:
Example 1: Preparation of sterile sodium amoxicillin using methyl acetate as solvent. The specific operations were as follows:
1. amoxicillin trihydrate (50 g) was dissolved in a solvent mixture of methyl acetate (92 mL), triethylamine (34 g) and methanol (52 mL).
2. The reaction mixture was stirred continuously at a temperature of 0-5°C until a clarified solution was formed, followed by filtration through a sterile filtration system.
3. sodium 2-ethylhexanoate (34 g) was dissolved in a solvent mixture of methyl acetate (92 mL) and methanol (52 mL) and filtered through a sterile filtration system.
4. The sodium 2-ethylhexanoate solution prepared in Step 3 was slowly added to the amoxicillin trihydrate solution from Step 2, maintaining the reaction temperature between 0-5°C.
5. After 80 minutes of reaction, methyl acetate (10 mL) was added to promote precipitation of the product.
6. The precipitate was collected by filtration, washed with methyl acetate (240 mL) and dried at a temperature lower than 50 °C, resulting in sterile sodium amoxicillin. Product yield was >90%.
[1] Patent: WO2011/158133, 2011, A1. Location in patent: Page/Page column 7
[2] Patent: WO2006/72577, 2006, A1. Location in patent: Page/Page column 9
[3] Patent: WO2006/72577, 2006, A1. Location in patent: Page/Page column 11