structure of piperacillin amide

piperacillin amide

CAS No.: 90686-52-5
M. Wt: 516.570
M. Fa: C23H28N6O6S
InChI Key: -

Names and Identifiers of piperacillin amide

CAS Number

90686-52-5

IUPAC Name

(2S,5R,6R)-6-[[2-[[4-ethyl-2,3-bis(oxidanylidene)piperazin-1-yl]carbonylamino]-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxidanylidene-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide

Canonical SMILES

CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)N

Physical and chemical properties of piperacillin amide

Density

1.5±0.1 g/cm3

Exact Mass

516.179077

Index of Refraction

1.677

LogP

0.69

Molecular Formula

C23H28N6O6S

Molecular Weight

516.570

Applications of piperacillin amide

Piperacillin amide is primarily used in clinical settings as an antibiotic for treating serious infections caused by susceptible organisms. Its applications include:

  • Infectious Diseases: Effective against severe infections such as pneumonia, sepsis, and intra-abdominal infections.
  • Surgical Prophylaxis: Used in preventing infections during surgical procedures, particularly in patients at high risk for infections.
  • Combination Therapy: Often used in conjunction with beta-lactamase inhibitors like tazobactam to enhance its spectrum of activity against resistant bacteria.

Interaction Studies of piperacillin amide

Studies have shown that piperacillin can interact chemically with other antibiotics, notably aminoglycosides such as gentamicin. These interactions may lead to reduced efficacy due to the formation of inactive complexes through nucleophilic attacks on the carboxylate groups present in piperacillin. Such interactions necessitate careful consideration when co-administering these drugs in clinical settings.

Furthermore, research into the pharmacokinetics and dynamics of piperacillin has indicated that renal function significantly affects its elimination half-life, which is critical for dosing adjustments in patients with renal impairment.

Biological Activity of piperacillin amide

Piperacillin amide exhibits significant antibacterial activity by inhibiting bacterial cell wall synthesis. It binds to penicillin-binding proteins (PBPs), disrupting the final stages of peptidoglycan synthesis and leading to cell lysis. This mechanism is particularly effective against a range of pathogens, including Escherichia coli and Pseudomonas aeruginosa, making it a valuable option in treating infections caused by these organisms.

The compound's efficacy is enhanced when combined with beta-lactamase inhibitors like tazobactam, as this combination can overcome resistance mechanisms employed by some bacteria. Piperacillin-tazobactam has shown synergistic effects against multidrug-resistant strains.