Ampicillin

General Information
Ampicillin Impurities and Ampicillin

Daicel Pharma offers high-quality Ampicillin impurities, Ampicillin hydantoin, and Ampicillin Impurity B. They are vital for the evaluation of the quality, stability, and biological safety of Ampicillin. Furthermore, Daicel Pharma specializes in the custom synthesis of Ampicillin impurities and ensures their worldwide delivery.

Ampicillin [CAS: 69-53-4] is a semi-synthetic derivative of penicillin, a broad-spectrum antibiotic. The penam ring of penicillin is substituted at the 6th position with a 2-amino-2-phenylacetamido group. It is a beta-lactam antibiotic and a known penicillin allergen. Ampicillin is an antibacterial conjugate acid of ampicillin (1-).

Ampicillin: Use and Commercial Availability

Ampicillin, available under various trade names such as Omnipen, Principen, Omnipen-N, and Totacillin-N, is a medication used to treat specific bacterial infections. Ampicillin is synthetically created and classified as a beta-lactam compound. Ampicillin’s stability against degradation by various beta-lactamases enables its utilization in treating many gram-positive and gram-negative infections.

Ampicillin Structure and Mechanism of Action

The chemical name of Ampicillin is (2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. The chemical formula for Ampicillin is C16H19N3O4S, and its molecular weight is approximately 349.4g/mol.

It exhibits bactericidal effects by binding to penicillin-binding proteins (PBPs) located within the bacterial cell wall’s inner membrane. This binding leads to the inactivation of PBPs, disrupting the cross-linkage of peptidoglycan chains crucial for maintaining bacterial cell wall strength and structure. Consequently, bacterial cell wall synthesis is impeded, weakening the wall and causing cell lysis.

Ampicillin Impurities and Synthesis

Like any pharmaceutical drug, Ampicillin may contain impurities affecting its safety and efficacy. These impurities form during the synthetic process, storage, or drug degradation. Impurities such as L-Ampicillin or Ampicillin Impurity B1 may arise due to traces of L-phenyl glycine methyl ester in D-phenyl glycine methyl ester hydrochloride. Therefore, to ensure the safety and quality of Ampicillin, these impurities must be controlled and monitored throughout the drug’s lifecycle, from production to patient administration.

Daicel Pharma offers a comprehensive Certificate of Analysis (CoA) for Ampicillin impurities, which includes Ampicillin hydantoin and Ampicillin Impurity B. This CoA is from a cGMP-compliant analytical facility and encompasses complete characterization data such as 1H NMR, 13C NMR, IR, MASS, and HPLC purity2. We provide additional data like 13C-DEPT and CHN on request. Daicel Pharma can prepare any unidentified Ampicillin impurity or degradation product. We can provide labeled compounds to measure the effectiveness of generic Ampicillin. Furthermore, Daicel offers highly purified isotope-labeled standards of Ampicillin. We provide a complete characterization report upon delivery.