Meropenem

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Cat Number

API96036032

CAS Number

96036-03-2

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Product Detail Description Scientific Support Customer Q&A

CAS Number

96036-03-2

EINECS

641-424-1

Storage

Store at 2-8°C

Synonyms

Merrem; Meropenem anhydrous; Meropenemum; MERONEM; MEPM; SM-7338; Meropenem, anhydrous; ICI-194660

Molecular Formula

C17H25N3O5S

Molecular Weight

383.5

Smiles

C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O

Appearance

White to pale yellow crystalline powder

Boiling Point

627.4±55.0°C (Predicted)

Relative Density

1.4±0.1

General Description

Meropenem is a broad-spectrum carbapenem antibiotic with a pyrrolidine side chain that confers stability against renal dehydropeptidase-1 (DHP-1), eliminating the need for co-administration with cilastatin. Its structure is a β-lactam with a 1-methyl-1-pyrrolidinyl group and a 2-aminocarbonyl group.

Mechanism of Action

Meropenem 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, and its rapid penetration through the outer membrane.

Application

Meropenem is indicated for the treatment of complicated intra-abdominal infections, community-acquired and 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 effective against Streptococcus pneumoniae, Haemophilus influenzae, and Neisseria meningitidis.

In a randomized trial (379 patients with ceftriaxone-nonsusceptible E. coli or K. pneumoniae bloodstream infection), piperacillin-tazobactam was noninferior to meropenem for 30-day mortality (12.3% vs 3.7%, risk difference 8.6%, P=0.90 for noninferiority).

Fig. 1 Patient Recruitment, Randomization, and Flow Through Study. (Harris PNA, et al., 2018)

References

Harris PNA, et al. Effect of Piperacillin-Tazobactam vs Meropenem on 30-Day Mortality for Patients With E coli or Klebsiella pneumoniae Bloodstream Infection and Ceftriaxone Resistance: A Randomized Clinical Trial. JAMA. 2018;320(10):984-994.

Does Meropenem 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 Meropenem sensitive to light and moisture during storage?

Yes, it is photosensitive and hygroscopic. Store in original, tightly sealed, light-resistant containers with desiccant under refrigeration.

What is the stability of Meropenem after reconstitution for intravenous infusion?

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

How is the impurity meropenem 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.