Ceftolozane | CAS#689293-68-3 | antibiotics

MedKoo Cat#: 314256 | Name: Ceftolozane

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ceftolozane is a fifth-generation cephalosporin antibiotic with potent activity against Pseudomonas aeruginosa, including multidrug-resistant strains, and various Enterobacteriaceae. It exhibits bactericidal action by inhibiting penicillin-binding proteins (PBPs), disrupting bacterial cell wall synthesis. In vitro, ceftolozane shows MIC<sub>90</sub> values of 1–4 µg/mL against most P. aeruginosa strains, including some resistant to other β-lactams. When combined with the β-lactamase inhibitor tazobactam (as in ceftolozane/tazobactam), its spectrum extends to include many ESBL-producing E. coli and K. pneumoniae, with MIC<sub>90</sub> values often ≤2 µg/mL.

Chemical Structure

Ceftolozane

CAS#689293-68-3 (free base)

Theoretical Analysis

MedKoo Cat#: 314256

Name: Ceftolozane

CAS#: 689293-68-3 (free base)

Chemical Formula: C23H30N12O8S2

Exact Mass: 666.1751

Molecular Weight: 666.69

Elemental Analysis: C, 41.44; H, 4.54; N, 25.21; O, 19.20; S, 9.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

689293-68-3 (free base) 936111-69-2 (sulfate)

Synonym

CXA-101; CXA101; CXA 101; FR264205; FR 264205; FR-264205; Ceftolozane brand name: Zerbaxa (with tazobactam).

IUPAC/Chemical Name

(6R,7R)-7-((Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(((2-carboxypropan-2-yl)oxy)imino)acetamido)-3-((5-amino-4-(3-(2-aminoethyl)ureido)-1-methyl-1H-pyrazol-2-ium-2-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

InChi Key

JHFNIHVVXRKLEF-DCZLAGFPSA-N

InChi Code

InChI=1S/C23H30N12O8S2/c1-23(2,20(40)41)43-31-11(15-30-21(26)45-32-15)16(36)29-12-17(37)35-13(19(38)39)9(8-44-18(12)35)6-34-7-10(14(25)33(34)3)28-22(42)27-5-4-24/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42)/b31-11-/t12-,18-/m1/s1

SMILES Code

O=C(C(N12)=C(C[N+]3=CC(NC(NCCN)=O)=C(N)N3C)CS[C@]2([H])[C@H](NC(/C(C4=NSC(N)=N4)=N\OC(C)(C(O)=O)C)=O)C1=O)[O-]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 666.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Eckmann C, Solomkin J. Ceftolozane/tazobactam for the treatment of complicated intra-abdominal infections. Expert Opin Pharmacother. 2015 Feb;16(2):271-80. doi: 10.1517/14656566.2015.994504. Epub 2014 Dec 22. PubMed PMID: 25529765. 2: Sorbera M, Chung E, Ho CW, Marzella N. Ceftolozane/Tazobactam: a new option in the treatment of complicated gram-negative infections. P T. 2014 Dec;39(12):825-32. PubMed PMID: 25516692; PubMed Central PMCID: PMC4264669. 3: Chandorkar G, Xiao A, Mouksassi MS, Hershberger E, Krishna G. Population pharmacokinetics of ceftolozane/tazobactam in healthy volunteers, subjects with varying degrees of renal function and patients with bacterial infections. J Clin Pharmacol. 2015 Feb;55(2):230-9. doi: 10.1002/jcph.395. Epub 2014 Nov 14. PubMed PMID: 25196976; PubMed Central PMCID: PMC4303958. 4: Estabrook M, Bussell B, Clugston SL, Bush K. In vitro activity of ceftolozane-tazobactam as determined by broth dilution and agar diffusion assays against recent U.S. Escherichia coli isolates from 2010 to 2011 carrying CTX-M-type extended-spectrum β-lactamases. J Clin Microbiol. 2014 Nov;52(11):4049-52. doi: 10.1128/JCM.02357-14. Epub 2014 Aug 20. PubMed PMID: 25143578; PubMed Central PMCID: PMC4313250. 5: Maseda E, Aguilar L, Gimenez MJ, Gilsanz F. Ceftolozane/tazobactam (CXA 201) for the treatment of intra-abdominal infections. Expert Rev Anti Infect Ther. 2014 Nov;12(11):1311-24. doi: 10.1586/14787210.2014.950230. Epub 2014 Aug 20. PubMed PMID: 25139127. 6: BretonniÃ¨re C, Boutoille D, Caillon J, Desessard C, Guitton C, Potel G, Jacqueline C. In vivo efficacy of ceftolozane against Pseudomonas aeruginosa in a rabbit experimental model of pneumonia: comparison with ceftazidime, piperacillin/tazobactam and imipenem. Int J Antimicrob Agents. 2014 Sep;44(3):218-21. doi: 10.1016/j.ijantimicag.2014.04.017. Epub 2014 Jun 6. PubMed PMID: 25108877. 7: Lepak AJ, Reda A, Marchillo K, Van Hecker J, Craig WA, Andes D. Impact of MIC range for Pseudomonas aeruginosa and Streptococcus pneumoniae on the ceftolozane in vivo pharmacokinetic/pharmacodynamic target. Antimicrob Agents Chemother. 2014 Oct;58(10):6311-4. doi: 10.1128/AAC.03572-14. Epub 2014 Aug 4. PubMed PMID: 25092700; PubMed Central PMCID: PMC4187960. 8: VanScoy BD, Mendes RE, Castanheira M, McCauley J, Bhavnani SM, Jones RN, Friedrich LV, Steenbergen JN, Ambrose PG. Relationship between ceftolozane-tazobactam exposure and selection for Pseudomonas aeruginosa resistance in a hollow-fiber infection model. Antimicrob Agents Chemother. 2014 Oct;58(10):6024-31. doi: 10.1128/AAC.02310-13. Epub 2014 Jul 28. PubMed PMID: 25070105; PubMed Central PMCID: PMC4187943. 9: Lucasti C, Hershberger E, Miller B, Yankelev S, Steenbergen J, Friedland I, Solomkin J. Multicenter, double-blind, randomized, phase II trial to assess the safety and efficacy of ceftolozane-tazobactam plus metronidazole compared with meropenem in adult patients with complicated intra-abdominal infections. Antimicrob Agents Chemother. 2014 Sep;58(9):5350-7. doi: 10.1128/AAC.00049-14. Epub 2014 Jun 30. PubMed PMID: 24982069; PubMed Central PMCID: PMC4135839. 10: Sader HS, Farrell DJ, Castanheira M, Flamm RK, Jones RN. Antimicrobial activity of ceftolozane/tazobactam tested against Pseudomonas aeruginosa and Enterobacteriaceae with various resistance patterns isolated in European hospitals (2011-12). J Antimicrob Chemother. 2014 Oct;69(10):2713-22. doi: 10.1093/jac/dku184. Epub 2014 Jun 10. PubMed PMID: 24917579.