Cefuroxime Axetil

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Cat Number

API64544076

CAS Number

64544-07-6

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Product Detail Description Scientific Support Customer Q&A

CAS Number

64544-07-6

EINECS

918-968-6

Storage

Store at 2-8℃

Synonyms

Ceftin; Elobact; Zinnat; Zinat; Cepazine; Cetoxil; Cefurax; Oraxim; Curocef; Novador; Novocef; CCI 15641

Molecular Formula

C20H22N4O10S

Molecular Weight

510.5

Smiles

CC(OC(=O)C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\OC)/C3=CC=CO3)COC(=O)N

Appearance

White to light yellow crystalline powder

Melting Point

175-180℃

General Description

Cefuroxime axetil is an oral prodrug of cefuroxime, a second-generation cephalosporin antibiotic with enhanced stability against beta-lactamases. The axetil ester improves gastrointestinal absorption and is hydrolyzed during intestinal uptake to release active cefuroxime. It is available in tablets and oral suspension, providing a convenient oral option for systemic infections.

Mechanism of Action

After absorption and de-esterification, cefuroxime binds to penicillin-binding proteins (PBPs) and inhibits the final transpeptidation step of bacterial cell wall synthesis. This disrupts peptidoglycan cross-linking, leading to osmotic lysis and bacterial death. The drug is bactericidal and has good stability against many beta-lactamases produced by gram-negative organisms, though it is not active against extended-spectrum beta-lactamase producers or Pseudomonas aeruginosa.

Application

It is indicated for the treatment of mild to moderate infections caused by susceptible organisms, including pharyngitis, otitis media, sinusitis, lower respiratory tract infections, uncomplicated urinary tract infections, and Lyme disease (early localized). It is also used as step-down therapy following intravenous cefuroxime. Common adverse effects include diarrhea and nausea. The oral suspension has a bitter taste that may affect compliance in children.

To improve the poor water solubility of the cephalosporin cefuroxime axetil (CFA), the authors prepared inclusion complexes with β‑cyclodextrin (βCD) with or without L‑arginine (ARG) as a ternary component. Phase solubility studies showed an A_L‑type curve, but the addition of ARG significantly increased both the complexation efficiency and the association constant. Spray‑dried ternary systems (CFA‑βCD‑ARG) exhibited superior solubility and dissolution rates compared to binary complexes (CFA‑βCD) or CFA alone, as confirmed by DSC, XRPD, and SEM. Molecular modeling clarified the inclusion geometry. The authors conclude that ARG is a valuable ternary component to enhance βCD‑based formulation of poorly soluble drugs.

Fig. 1 The dissolution profile of CFA, binary and ternary inclusion complexes at 37±0.5 °C. (Sapte S, Pore Y, 2016)

References

Sapte S, Pore Y. Inclusion complexes of cefuroxime axetil with β-cyclodextrin: Physicochemical characterization, molecular modeling and effect of l-arginine on complexation. J Pharm Anal. 2016; 6(5):300-306.

Does Cefuroxime Axetil require refrigerated storage as a cephalosporin antibiotic?

Yes, it should be stored at 2-8°C for long-term stability. At room temperature, hydrolysis of the beta-lactam ring and the axetil ester accelerates rapidly.

Is Cefuroxime Axetil sensitive to moisture, and how is this prevented?

Extremely. It is hygroscopic and readily hydrolyzes. Our packaging includes triple-layer moisture-barrier foil bags with desiccant, and we recommend storage in low-humidity conditions.

What is the stability of Cefuroxime Axetil in oral suspension formulations?

Reconstituted suspensions have limited stability (typically 7-10 days under refrigeration).

How is the impurity Δ3-cefuroxime axetil monitored during stability?

This key degradation product is quantified using a stability-indicating HPLC method, ensuring it remains below pharmacopoeial limits throughout shelf life.