Amino penicillins

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Chapter: Medicinal Chemistry : Antibiotics

Amino penicillins : i. Ampicillin (Amcil, Omnipen) ii. Pivampicillin


Penicillin - Synthesis and Drug Profile

Amino penicillins

i. Ampicillin (Amcil, Omnipen)


Synthesis


Properties and uses: Ampicillin is a white hygroscopic powder, freely soluble in water, sparingly soluble in acetone, practically insoluble in fatty oils and liquid paraffin. The corresponding product from acylation with 2-azido-4-hydroxyphenyl acetyl chloride is amoxicillin. The protonated α-amino group of ampicillin has a pKa of 7.3 and is thus extensively protonated in acidic media, which explains ampicillin’s stability towards acid hydrolysis and instability towards alkaline hydrolysis. The α-amino group plays an important role in the broader activity. It is used to treat urinary tract infections and respiratory tract infections.

Assay: It is assayed by adopting liquid chromatography technique.

Dose: Available as capsules of 250 or 500 mg, as sodium salt for parenteral use, for oral suspension in strengths of 125–500mg/5ml, and in paediatric drops of 100 mg/ml. The consumption dose for adults is 1–4 g per day in divided dose for every 6 h, for children the dose is 100–200 mg/kg per day in three portions.

Dosage forms: Ampicillin capsules I.P., Ampicillin sodium injection I.P., Ampicillin injection B.P.

 

ii. Pivampicillin


Synthesis


Properties and uses: Pivampicillin is a white crystalline powder, practically insoluble in water, soluble in methanol, ethanol, and dilute acids. It is a produg for ampicillin and in the in vivo esters hydrolyzes back to the parent ampicillin. It is used to treat urinary tract infections and respiratory tract infections.

Assay: It is assayed by adopting liquid chromatography technique.

 

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