Imipenem

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Cat Number

API0232315

CAS Number

64221-86-9

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CAS Number

64221-86-9

EINECS

264-734-5

Storage

Store at 2-8°C

Synonyms

Imipemide; N-Formimidoylthienamycin; Imipenem anhydrous; Imipenemum

Molecular Formula

C12H17N3O4S

Molecular Weight

299.35

Smiles

C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O

Appearance

White to off-white powder

Melting Point

106-111°C

Boiling Point

530.2±60.0°C at 760 mmHg (Predicted)

Relative Density

1.62±0.1 (Predicted)

General Description

Imipenem is a synthetic carbapenem antibiotic, a β-lactam with a pyrrolidine side chain, which belongs to the class of carbapenems. Its chemical structure is (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid. Imipenem is a white to off-white powder, soluble in water.

Mechanism of Action

Imipenem inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs), particularly PBP2 and PBP3 in gram-negative organisms, disrupting peptidoglycan cross-linking. Its potent activity against a broad spectrum of gram-positive and gram-negative bacteria, including anaerobes and Pseudomonas aeruginosa, is attributed to its high stability against most β-lactamases, including ESBLs and AmpC.

Application

Imipenem is indicated for the treatment of complicated intra-abdominal infections, nosocomial pneumonia, complicated urinary tract infections, and febrile neutropenia. It is also used for empiric therapy in critically ill patients and for infections caused by multidrug-resistant organisms. The drug is administered in combination with cilastatin to prevent renal metabolism.

Imipenem‑loaded polycaprolactone (PCL) nanocapsules enhanced antimicrobial activity against imipenem‑resistant Klebsiella pneumoniae and Pseudomonas aeruginosa, achieving faster bacterial killing (2‑3 hours) than free drug or PLGA formulations. They protected imipenem from enzymatic degradation, lowered mutation prevention concentration, and reduced biofilm formation by >74%. Polymeric nanoparticles could restore imipenem efficacy against MDR pathogens.

Fig. 1 FTIR spectrum of imipenem/cilastatin (IMP), polycaprolactone nanoparticles (PCL), imipenem/cilastatin loaded polycaprolactone nanoparticles (IMP/PCL), polylactide-co-glycolide nanoparticles (PLGA), and imipenem/cilastatin loaded polylactide-co-glycolide nanoparticles (IMP/PLGA). (Shaaban MI, et al., 2017)

References

Shaaban MI, et al. Imipenem/cilastatin encapsulated polymeric nanoparticles for destroying carbapenem-resistant bacterial isolates. J Nanobiotechnology. 2017;15(1):29.

A MALDI‑TOF MS‑based method was developed for rapid detection of carbapenemases in P. aeruginosa using imipenem/relebactam hydrolysis. The method showed 98% agreement with phenotype and 100% concordance with genotype in 250 prospective clinical isolates (except GES enzymes), with results within 1 hour. This rapid test supports appropriate use of imipenem/relebactam in severe P. aeruginosa infections.

Fig. 2 Variation of the MALDI-TOF MS RH for imipenem with different concentrations of relebactam. (Candela A, et al., 2025)

References

Candela A, et al. Rapid prediction of carbapenemases in Pseudomonas aeruginosa by imipenem/relebactam and MALDI-TOF MS. J Clin Microbiol. 2025;63(5):e0110524.

Does Imipenem require strict cold chain storage as a carbapenem antibiotic?

Yes, it must be stored at 2–8°C. At room temperature, rapid hydrolysis of the beta-lactam ring occurs, reducing antibacterial activity.

Is Imipenem extremely sensitive to moisture, and how is this prevented?

Yes, it is highly hygroscopic. Our packaging includes moisture-barrier foil bags with desiccant. Open only in low-humidity environments under refrigeration.

What is the stability of Imipenem after reconstitution for intravenous infusion (in combination with cilastatin)?

Reconstituted solutions are stable for up to 24 hours under refrigeration and 6 hours at room temperature.

How is the impurity imipenem ring-opened acid (a hydrolysis product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within ICH limits.