Ceftolozane

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MedKoo CAT#: 314256

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

Description: Ceftolozane, also known as FR-264,205 and CXA-101; is an antibiotic drug from the cephalosporin family, approved for the treatment of infections with gram-negative bacteria, or gram-positive bacteria. Ceftolozane is of great benefit due to its ability to target bacteria that have become resistant to conventional antibiotics. Ceftolozane is combined with the β-lactamase inhibitor tazobactam, as multi-drug resistant bacterial infections will generally show resistance to all β-lactam antibiotics unless this enzyme is inhibited. .


Chemical Structure

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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

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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

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.

Recalculate based on batch purity %
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

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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: Bretonnière 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.