U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30N12O8S2
Molecular Weight 666.693
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTOLOZANE

SMILES

CC(C)(C(=O)O)O/N=C(/c1nc(=N)s[nH]1)\C(=N[C@]2([H])C(=O)N3C(=C(Cn4cc(c(N)[n+]4C)NC(=NCCN)O)CS[C@]23[H])C(=O)O)[O-]

InChI

InChIKey=JHFNIHVVXRKLEF-DCZLAGFPSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created using several sources including: http://www.ncbi.nlm.nih.gov/pubmed/18701284; http://www.ncbi.nlm.nih.gov/pubmed/17145788; http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4264669/

Ceftolozane is a novel a cephalosporin-class antibacterial drug. In combination with a beta-lactamase inhibitor tazobactam (ZERBAXA, ceftolozane/tazobactam ) ceftolozane, is currently indicated for the treatment of the adult patients with complicated intra-abdominal infections caused by designated Gram-negative and Gram-positive microorganisms and complicated urinary tract infections caused by certain Gram-negative bacteria, including those caused by multi-drug resistant Pseudomonas aeruginosa. To reduce the development of drug-resistant bacteria and maintain the effectiveness of ZERBAXA and other antibacterial drugs, ZERBAXA should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. Safety and effectiveness in pediatric patients have not been established.

Originator

Curator's Comment:: In December 2009 Cubist Pharmaceuticals, Inc. obtained the rights to ceftolozane from Astellas Pharma outside of Asia-Pacific and Middle East territories. Since March 2013 Cubist owns worldwide rights to develop, manufacture, and commercialize ceftolozane/tazobactam.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ZERBAXA

Approved Use

To treat adults with complicated intra-abdominal infections (cIAI) and complicated urinary tract infections (cUTI)

Launch Date

1.4189472E12
Curative
ZERBAXA

Approved Use

To treat adults with complicated intra-abdominal infections (cIAI) and complicated urinary tract infections (cUTI).

Launch Date

1.4189472E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
69.1 μg/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
74.4 μg/mL
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
172 μg × h/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
182 μg × h/mL
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.77 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.12 h
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
81.5%
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
81.5%
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2000 mg single, intravenous
Highest studied dose
Dose: 2000 mg
Route: intravenous
Route: single
Dose: 2000 mg
Sources:
healthy, 29.5 years (range: 19–59 years)
n = 6
Health Status: healthy
Age Group: 29.5 years (range: 19–59 years)
Sex: M+F
Population Size: 6
Sources:
1000 mg 3 times / day steady, intravenous
Highest studied dose
Dose: 1000 mg, 3 times / day
Route: intravenous
Route: steady
Dose: 1000 mg, 3 times / day
Sources:
healthy, 33.0 years (range: 22–55 years)
n = 6
Health Status: healthy
Age Group: 33.0 years (range: 22–55 years)
Sex: M+F
Population Size: 6
Sources:
Other AEs: Flushing...
Other AEs:
Flushing (1 patient)
Sources:
1500 mg 2 times / day steady, intravenous
Highest studied dose
Dose: 1500 mg, 2 times / day
Route: intravenous
Route: steady
Dose: 1500 mg, 2 times / day
Sources:
healthy, 33.0 years (range: 22–55 years)
n = 6
Health Status: healthy
Age Group: 33.0 years (range: 22–55 years)
Sex: M+F
Population Size: 6
Sources:
AEs

AEs

AESignificanceDosePopulation
Flushing 1 patient
1000 mg 3 times / day steady, intravenous
Highest studied dose
Dose: 1000 mg, 3 times / day
Route: intravenous
Route: steady
Dose: 1000 mg, 3 times / day
Sources:
healthy, 33.0 years (range: 22–55 years)
n = 6
Health Status: healthy
Age Group: 33.0 years (range: 22–55 years)
Sex: M+F
Population Size: 6
Sources:
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
weak [IC50 >3754 uM]
weak [IC50 >3754 uM]
weak [IC50 >3754 uM]
weak [IC50 >3754 uM]
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Ceftolozane/Tazobactam: a new option in the treatment of complicated gram-negative infections.
2014 Dec
Ceftolozane/tazobactam: a novel cephalosporin/β-lactamase inhibitor combination with activity against multidrug-resistant gram-negative bacilli.
2014 Jan
Patents

Patents

Sample Use Guides

1.5 gram (g) (ceftolozane 1 g and tazobactam 0.5 g) for injection, every 8 hours by intravenous infusion administered over 1 hour for patients 18 years or older with creatinine clearance (CrCl) greater than 50 mL/min
Route of Administration: Intravenous
Minimum inhibitory concentrations (MIC) were obtained for ceftolozane and tazobactam in the susceptibility testing using fixed 4 ug/mL concentration of tazobactam and less then 8 ug/mL for susceptible bacteria
Name Type Language
CEFTOLOZANE
DASH   INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
CXA-101 FREE BASE
Code English
CEFTOLOZANE [MI]
Common Name English
CEFTOLOZANE [WHO-DD]
Common Name English
(6R,7R)-3-((5-AMINO-4-(((2-AMINOETHYL)CARBAMOYL)AMINO)-1-METHYL-1H-PYRAZOL-2-IUM-2-YL)METHYL)-7-((2Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-(((2-CARBOXYPROPAN-2-YL)OXY)IMINO)ACETAMIDO)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE
Common Name English
CEFTOLOZANE [USAN]
Common Name English
CEFTOLOZANE [INN]
Common Name English
CEFTOLOZANE [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175488
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
WHO-ATC J01DI54
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
NCI_THESAURUS C357
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
Code System Code Type Description
CAS
689293-68-3
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
ChEMBL
CHEMBL2103872
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
WIKIPEDIA
Ceftolozane
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
EVMPD
SUB167762
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
RXCUI
1597609
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY RxNorm
PUBCHEM
53234134
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
INN
9426
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
MERCK INDEX
M3224
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C150024
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
LACTMED
Ceftolozane and Tazobactam
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
DRUG CENTRAL
4922
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
FDA UNII
37A4IES95Q
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY
DRUG BANK
DB09050
Created by admin on Sat Jun 26 10:27:34 UTC 2021 , Edited by admin on Sat Jun 26 10:27:34 UTC 2021
PRIMARY