Identification

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Name
Ceftolozane
Accession Number
DB09050
Type
Small Molecule
Groups
Approved, Investigational
Description

Ceftolozane is a semi-synthetic broad-spectrum fifth generation cephalosporin.10 It was approved by the FDA in 2014 for use in combination with Tazobactam for the treatment of serious infections, such as intra-abdominal infections and complicated urinary tract infections. The manufacturer of this drug is Cubist Pharmaceuticals.3 Most recently, in June 2019, ceftolozane-tazobactam was approved for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia.Label

Hospital-acquired pneumonia and ventilator-associated pneumonia are major causes of morbidity and mortality in hospitalized patients and the use of ceftolozane-tazobactam offers effective activity against various organisms causing these infections, such as Pseudomonas aeruginosa.12

Structure
Thumb
Synonyms
  • (6R,7R)-3-([3-Amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl)-7-([(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • Ceftolozane
  • ceftolozano
External IDs
CXA-101 / FR-264,205
Product Ingredients
IngredientUNIICASInChI Key
Ceftolozane sulfate7R247U84HY936111-69-2UJDQGRLTPBVSFN-TVNHLQOTSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ZerbaxaCeftolozane (1 g) + Tazobactam (0.5 g)Powder, for solutionIntravenousMerck Ltd.2016-01-12Not applicableCanada
ZerbaxaCeftolozane sulfate (1 g/10mL) + Tazobactam sodium (0.5 g/10mL)Injection, powder, lyophilized, for solutionIntravenousMerck Sharp & Dohme Corp.2014-12-19Not applicableUs
Categories
UNII
37A4IES95Q
CAS number
689293-68-3
Weight
Average: 666.69
Monoisotopic: 666.175098322
Chemical Formula
C23H30N12O8S2
InChI Key
JHFNIHVVXRKLEF-DCZLAGFPSA-N
InChI
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
IUPAC Name
5-amino-2-{[(6R,7R)-7-[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-4-{[(2-aminoethyl)carbamoyl]amino}-1-methyl-1H-pyrazol-2-ium
SMILES
CN1C(N)=C(NC(=O)NCCN)C=[N+]1CC1=C(N2[C@H](SC1)[C@H](NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=NSC(N)=N1)C2=O)C([O-])=O

Pharmacology

Indication

This drug is administered in combination with tazobactam for the treatment of complicated intra-abdominal infections (in combination with metronidazole) and complicated urinary tract infections4, which may include pyelonephritis. Ceftolozane-tazobactam is also indicated in the treatment of bacterial ventilator-associated pneumonia and bacterial hospital-acquired pneumonia.Label

Associated Conditions
Pharmacodynamics

Ceftolozane exerts bactericidal activities against susceptible gram-negative and gram-positive infections by interfering with bacterial cell wall synthesis.Label,5 When it is combined with tazobactam, it exerts further activity against beta-lactamase enzyme producing bacteria, which are normally resistant to beta-lactam antibiotics and interfere with infection treatment.Label,11 The addition of tazobactam strengthens the therapeutic response to ceftolozane, giving it the ability to treat a broader range of bacterial infections and resistant organisms.5,7,9

Mechanism of action

Ceftolozane belongs to the cephalosporin class of antibacterial drugs. Ceftolozane exerts antibacterial effects, preventing the formation of cell walls that protect bacteria from injury and confer resistance to some antibiotics. Its antibacterial activity is also mediated through ceftolozane binding to penicillin-binding proteins (PBPs), which are required for peptidoglycan cross-linking for bacterial cell wall synthesis. As a result of cell wall synthesis inhibition, bacterial cells are killed, treating various infections.7,6 Ceftolozane has a particularly high affinity to the penicillin-binding proteins for Pseudomonas aeruginosa and Escherichia coli as well as Klebsiella pneumoniae and other enteric bacteria.11 In particular, a high affinity has been seen in vitro for penicillin-binding proteins 1b, 1c, 2, and 3 when compared to other antibiotics, ceftazidime and imipenem. 8

TargetActionsOrganism
APenicillin-binding protein 1B
inhibitor
Pseudomonas aeruginosa
APenicillin-binding protein 3
inhibitor
Pseudomonas aeruginosa
UPenicillin-binding proteinNot AvailableGram positive and gram negative bacteria
APenicillin-binding protein 1C
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 2
inhibitor
Escherichia coli (strain K12)
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

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Blackbox Warnings

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Absorption

The area under the curve (AUC) of ceftolozane-tazobactam after an injected dose of 1 g/0.5 g every 8 hours for 1 day was 172 mcg•h/mLLabel. The Cmax (peak concentration) and AUC are dose-dependent. The Cmax on day one of the above dose of ceftolozane-tazobactam was 69.1 mcg/mL.Label

Volume of distribution

13.5 L Label Tissue distribution of ceftalozone-tazobactam is rapid and shows good penetration into the lung, rendering it an ideal treatment for bacterial pneumonia.7

Protein binding

16% to 21% bound to plasma proteins.Label

Metabolism

Certolozane is not metabolized to any significant extent.Label The beta-lactam ring of tazobactam, when administered as ceftolozane-tazobactam, is hydrolyzed to form an inactive metabolite.Label

Route of elimination

Ceftolozane is mainly excreted in the urine.Label,6

Half life

2.77 hours on day 1 of treatment on a dose of 1 g/0.5 g every 8 hours.Label,6 3.12 hours on day 10 of treatment on a dose of 1 g/0.5 g every 8 hours.Label

Clearance

The renal clearance of was measured to be 3.41 – 6.69 L/h after a single dose of ceftolozane-tazobactam. Dose adjustments of this drug are required in patients with impaired renal function with a creatinine clearance of 50 mL/min or below. Consult official labeling for dosing adjustment guidelines.Label,7

Toxicity

A note on nephrotoxicity

This drug is mainly excreted by the kidneys6, and if administered to a patient with a creatinine clearance of less than 50 mL/min, may cause renal damage. Consult official product labeling for dosing adjustments in patients with renal impairment.Label,7

Overdose information

If an overdose occurs, discontinue the drug and follow this with supportive treatment. Dialysis may be used.Label

Use in pregnancy

Ceftolozane-tazobactam is a pregnancy category B drug, but human studies have not been performed to validate this in humans. At doses equivalent to 4-7 the standard dose administered in humans, no developmental abnormalities were seen. Since animal studies are not always predictive of drug response in humans, it is advisable to exercise caution if this drug is prescribed during pregnancy. The mother's clinical need should be assessed as well as possible risks to the fetus.Label

Use in lactation

Whether this drug is excreted in human breast milk is unknown. Caution is advised if this drug is administered during lactation, as many other drugs are known to be secreted into breast milk.Label

Carcinogenesis/mutagenesis

Formal studies have not been conducted in humans to assess mutagenicity or carcinogenicity. Studies in mice and rats did not reveal any mutagenic or carcinogenic potential, however, the potential risks resulting from long-term use have not been studied.Label

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Ceftolozane is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Ceftolozane is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Ceftolozane is combined with 4-hydroxycoumarin.
AbacavirAbacavir may decrease the excretion rate of Ceftolozane which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Ceftolozane.
AcarboseAcarbose may decrease the excretion rate of Ceftolozane which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ceftolozane which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ceftolozane which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Ceftolozane is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Ceftolozane which could result in a higher serum level.
Additional Data Available
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Food Interactions
Not Available

References

General References
  1. 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:25516692]
  2. Zhanel GG, Chung P, Adam H, Zelenitsky S, Denisuik A, Schweizer F, Lagace-Wiens PR, Rubinstein E, Gin AS, Walkty A, Hoban DJ, Lynch JP 3rd, Karlowsky JA: Ceftolozane/tazobactam: a novel cephalosporin/beta-lactamase inhibitor combination with activity against multidrug-resistant gram-negative bacilli. Drugs. 2014 Jan;74(1):31-51. doi: 10.1007/s40265-013-0168-2. [PubMed:24352909]
  3. Cluck D, Lewis P, Stayer B, Spivey J, Moorman J: Ceftolozane-tazobactam: A new-generation cephalosporin. Am J Health Syst Pharm. 2015 Dec 15;72(24):2135-46. doi: 10.2146/ajhp150049. [PubMed:26637512]
  4. Giacobbe DR, Bassetti M, De Rosa FG, Del Bono V, Grossi PA, Menichetti F, Pea F, Rossolini GM, Tumbarello M, Viale P, Viscoli C: Ceftolozane/tazobactam: place in therapy. Expert Rev Anti Infect Ther. 2018 Apr;16(4):307-320. doi: 10.1080/14787210.2018.1447381. Epub 2018 Mar 9. [PubMed:29493397]
  5. Shortridge D, Pfaller MA, Castanheira M, Flamm RK: Antimicrobial Activity of Ceftolozane-Tazobactam Tested Against Enterobacteriaceae and Pseudomonas aeruginosa with Various Resistance Patterns Isolated in U.S. Hospitals (2013-2016) as Part of the Surveillance Program: Program to Assess Ceftolozane-Tazobactam Susceptibility. Microb Drug Resist. 2018 Jun;24(5):563-577. doi: 10.1089/mdr.2017.0266. Epub 2017 Oct 17. [PubMed:29039729]
  6. Miller B, Hershberger E, Benziger D, Trinh M, Friedland I: Pharmacokinetics and safety of intravenous ceftolozane-tazobactam in healthy adult subjects following single and multiple ascending doses. Antimicrob Agents Chemother. 2012 Jun;56(6):3086-91. doi: 10.1128/AAC.06349-11. Epub 2012 Mar 26. [PubMed:22450972]
  7. Hong MC, Hsu DI, Bounthavong M: Ceftolozane/tazobactam: a novel antipseudomonal cephalosporin and beta-lactamase-inhibitor combination. Infect Drug Resist. 2013 Nov 29;6:215-23. doi: 10.2147/IDR.S36140. [PubMed:24348053]
  8. Moya B, Zamorano L, Juan C, Ge Y, Oliver A: Affinity of the new cephalosporin CXA-101 to penicillin-binding proteins of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2010 Sep;54(9):3933-7. doi: 10.1128/AAC.00296-10. Epub 2010 Jun 14. [PubMed:20547785]
  9. Shlaes DM: New beta-lactam-beta-lactamase inhibitor combinations in clinical development. Ann N Y Acad Sci. 2013 Jan;1277:105-14. doi: 10.1111/nyas.12010. [PubMed:23346860]
  10. Ceftolozane Pubchem [Link]
  11. Zerbaxa MedSafe NZ data sheet [Link]
  12. FDA news [Link]
External Links
KEGG Drug
D10097
PubChem Compound
53234134
PubChem Substance
310264994
ChemSpider
25999973
ChEBI
134719
ChEMBL
CHEMBL2103872
Wikipedia
Ceftolozane
FDA label
Download (424 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherDiabetes Mellitus (DM) / Healthy Volunteers / Wound Infections1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentCritically-ill Patients / Pneumonia1
1CompletedTreatmentPeri-operative Prophylaxis / Proven or Suspected Gram-negative Bacterial Infection1
1, 2Not Yet RecruitingBasic SciencePharmacokinetics1
2CompletedTreatmentComplicated Intra-Abdominal Infections1
2CompletedTreatmentComplicated Urinary Tract Infection1
2RecruitingTreatmentComplicated Intra-Abdominal Infections1
2RecruitingTreatmentComplicated Urinary Tract Infection / Pyelonephritis1
2RecruitingTreatmentOther Infectious Diseases1
3CompletedTreatmentChronic Lung Diseases / Healthcare-Associated Pneumonia / Hospital-acquired bacterial pneumonia / Ventilator-Associated Pneumonia (VAP)1
3CompletedTreatmentComplicated Intra-Abdominal Infections / Intra-Abdominal Infections1
3CompletedTreatmentComplicated Urinary Tract Infection / Pyelonephritis / Uncomplicated Pyelonephritis / Urinary Tract Infection1
3RecruitingTreatmentComplicated Intra-Abdominal Infections1
3RecruitingTreatmentVentilator-Associated Pneumonia (VAP)1
3TerminatedTreatmentVentilator-Associated Pneumonia (VAP)1
4CompletedOtherCystic Fibrosis (CF) / Cystic Fibrosis Pulmonary Exacerbation / Pseudomonas Aeruginosa Infection1
4RecruitingOtherMinor burns / Pharmacokinetics1
Not AvailableActive Not RecruitingNot AvailablePseudomonas Aeruginosa / Pseudomonas Infections1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Injury (AKI) / Haemodiafiltration / Sepsis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous
Powder, for solutionIntravenous
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US20140274993No2013-03-152033-03-15Us
US2014144295No2013-03-152033-03-15Us
US20140274991No2013-03-152033-03-15Us
US20140262868No2013-03-152033-03-15Us
US7129232No2006-10-312024-10-21Us
US8685957No2014-04-012032-09-27Us
US8968753No2015-03-032034-03-14Us
US8476425No2013-07-022032-09-27Us
US8906898No2014-12-092034-05-28Us
US9320740No2016-04-262034-03-14Us
US9872906No2018-01-232034-03-14Us
US10125149No2018-11-132035-08-14Us
US9724353No2017-08-082032-09-07Us
US10028963No2018-07-242032-09-07Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-6.17https://www.chemsrc.com/en/cas/689293-68-3_1197589.html
Predicted Properties
PropertyValueSource
Water Solubility0.0884 mg/mLALOGPS
logP-1.2ALOGPS
logP-8.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area302.21 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity194.51 m3·mol-1ChemAxon
Polarizability62.04 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / 1,3-thiazines / Dicarboxylic acids and derivatives / Thiadiazoles / Tertiary carboxylic acid amides / Pyrazoles / Heteroaromatic compounds / Ureas / Secondary carboxylic acid amides / Amino acids
show 13 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Meta-thiazine / Dicarboxylic acid or derivatives / Pyrazole / Tertiary carboxylic acid amide / Thiadiazole / Azole / Heteroaromatic compound
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
ponB
Uniprot ID
Q9X6W0
Uniprot Name
Penicillin-binding protein 1B
Molecular Weight
85486.615 Da
References
  1. 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:25516692]
  2. Moya B, Zamorano L, Juan C, Ge Y, Oliver A: Affinity of the new cephalosporin CXA-101 to penicillin-binding proteins of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2010 Sep;54(9):3933-7. doi: 10.1128/AAC.00296-10. Epub 2010 Jun 14. [PubMed:20547785]
  3. FDA label, Zerbaxa [Link]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Not Available
Gene Name
pbpB
Uniprot ID
Q51504
Uniprot Name
Cell division protein
Molecular Weight
62855.78 Da
References
  1. 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:25516692]
  2. Moya B, Zamorano L, Juan C, Ge Y, Oliver A: Affinity of the new cephalosporin CXA-101 to penicillin-binding proteins of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2010 Sep;54(9):3933-7. doi: 10.1128/AAC.00296-10. Epub 2010 Jun 14. [PubMed:20547785]
  3. FDA label, Zerbaxa [Link]
Kind
Protein group
Organism
Gram positive and gram negative bacteria
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.

Components:
References
  1. Moya B, Zamorano L, Juan C, Ge Y, Oliver A: Affinity of the new cephalosporin CXA-101 to penicillin-binding proteins of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2010 Sep;54(9):3933-7. doi: 10.1128/AAC.00296-10. Epub 2010 Jun 14. [PubMed:20547785]
  2. FDA label, Zerbaxa [Link]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Cell wall formation. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a transpeptidase C-terminal domain which may not be functional.
Gene Name
pbpC
Uniprot ID
P76577
Uniprot Name
Penicillin-binding protein 1C
Molecular Weight
85066.085 Da
References
  1. Moya B, Zamorano L, Juan C, Ge Y, Oliver A: Affinity of the new cephalosporin CXA-101 to penicillin-binding proteins of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2010 Sep;54(9):3933-7. doi: 10.1128/AAC.00296-10. Epub 2010 Jun 14. [PubMed:20547785]
  2. FDA label, Zerbaxa [Link]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. It synthesizes cross-linked peptidoglycan from lipid intermediates.
Gene Name
mrdA
Uniprot ID
P0AD65
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
70856.1 Da
References
  1. Moya B, Zamorano L, Juan C, Ge Y, Oliver A: Affinity of the new cephalosporin CXA-101 to penicillin-binding proteins of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2010 Sep;54(9):3933-7. doi: 10.1128/AAC.00296-10. Epub 2010 Jun 14. [PubMed:20547785]
  2. FDA label, Zerbaxa [Link]

Drug created on May 06, 2015 10:29 / Updated on November 02, 2019 04:28