Amoxicillin sodium Chemical Properties

Melting point:

130℃

Boiling point:

743℃

RTECS 

XH8300000

Flash point:

>110°(230°F)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Very soluble in water, sparingly soluble in anhydrous ethanol, very slightly soluble in acetone.

form 

Liquid

color 

White to light yellow

Water Solubility 

Soluble in water.

InChIKey

QLKRYDZJRDWEHH-AGYZSTNLNA-N

SMILES

C([C@H]1C(S[C@]2([H])[C@H](NC(=O)[C@@H](C3C=CC(O)=CC=3)N)C(=O)N12)(C)C)(=O)O.[NaH] |&1:1,4,6,10,r|

CAS DataBase Reference

34642-77-8(CAS DataBase Reference)

Amoxicillin sodium Usage And Synthesis

Chemical Properties

White or almost white, very hygroscopic, powder.

Uses

Antibiotic[Note—Amoxicillin sodium will be used in combination with clavulanate potassium and marketed as ‘‘Augmentin for intravenous administration’’].

Definition

ChEBI: Amoxicillin sodium is an organic sodium salt that is the monosodium salt of amoxicillin. It contains an amoxicillin(1-).

Contact allergens

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

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%.

References

[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
[4] Patent: WO2006/72577, 2006, A1. Location in patent: Page/Page column 11

Amoxicillin sodium(34642-77-8)Related Product Information

• Chlorodimethylphenylsilane
• Dimethicone
• Acetylacetone
• Amoxicillin
• Sodium chloride
• N,N-Dimethylformamide
• Dimethyl sulfone
• Acetyl coenzyme A sodium salt
• Sodium acetate
• Dimethyl sulfoxide
• Sodium hydroxide
• Sodium benzoate
• Diclofenac sodium
• N,N-Dimethyl-1,4-phenylenediamine
• Sodium bicarbonate
• N,N-Dimethylacetamide
• Poly(dimethylsiloxane)
• Sodium citrate