Ceftolozane Sulfate

Inquiry

Cat Number

API0232167

CAS Number

936111-69-2

If you have any other questions, please contact our experts.

Product Detail Description Scientific Support Customer Q&A

CAS Number

936111-69-2

EINECS

688-944-5

Storage

Store at 2-8°C

Synonyms

FR264205; 7R247U84HY; DTXSID001027693; ZERBAXA COMPONENT CEFTOLOZANE SULFATE; RefChem:918195; DTXCID601513274; CXA-101

Molecular Formula

C23H32N12O12S3

Molecular Weight

764.8

Smiles

CC(C)(C(=O)O)O/N=C(/C1=NSC(=N1)N)\\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC(=C(N4C)N)NC(=O)NCCN)C(=O)O.OS(=O)(=O)[O-]

Appearance

Off-white powder

General Description

Ceftolozane sulfate is a fifth‑generation cephalosporin with an acyl side chain derived from an aminothiadiazole and a pyrazole ring. Its chemical structure includes a 3‑aminopyrazolium group that enhances activity against Pseudomonas aeruginosa. The sulfate salt improves stability. Ceftolozane is a zwitterionic molecule that crosses the outer membrane of gram‑negative bacteria via porin channels.

Mechanism of Action

Ceftolozane binds to penicillin‑binding proteins (PBPs), particularly PBP1b and PBP3 in Pseudomonas aeruginosa and PBP3 in Enterobacteriaceae. This binding inhibits peptidoglycan cross‑linking, leading to cell lysis. The large 3‑aminopyrazolium substituent provides stability against many β‑lactamases, including AmpC and some extended‑spectrum β‑lactamases (ESBLs). Ceftolozane is not active against carbapenemase‑producing organisms unless combined with a β‑lactamase inhibitor.

Application

Ceftolozane is indicated in combination with tazobactam (a β‑lactamase inhibitor) for complicated urinary tract infections, complicated intra‑abdominal infections, and hospital‑acquired pneumonia (including ventilator‑associated pneumonia). It is particularly valuable against multidrug‑resistant Pseudomonas aeruginosa, including strains resistant to piperacillin‑tazobactam or meropenem.

Systematic review of 83 real‑world studies (3,701 patients) on ceftolozane/tazobactam (C/T) for gram‑negative infections, mostly in seriously ill patients with resistant Pseudomonas aeruginosa (90.7% of infections). Clinical success rates ranged from 45.7‑100% (69% of studies reporting >70%), microbiological success 31‑100% (74% reporting >70%), and mortality 0‑50% (69% reporting ≤20%). Comparative studies showed C/T as effective as, and sometimes significantly more effective than, aminoglycoside‑ or polymyxin‑based regimens. C/T is effective in real‑world practice and offers a successful alternative to standard of care.

Fig. 1 P. aeruginosa resistance profile in studies identified in 2015–2017 and 2018–2020. (Puzniak L, et al., 2021)

References

Puzniak L, et al. Real-world use of ceftolozane/tazobactam: a systematic literature review. Antimicrob Resist Infect Control. 2021;10(1):68.

Does Ceftolozane Sulfate require refrigerated storage as a cephalosporin antibiotic?

Yes, it must be stored at 2-8°C. At room temperature, rapid hydrolysis of the beta-lactam ring and degradation of the side chain occur.

Is Ceftolozane Sulfate sensitive to light and moisture?

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

What is the stability of Ceftolozane Sulfate 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 ceftolozane E-isomer (geometric isomer) monitored?

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