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

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H31N12O8S2.HO4S
Molecular Weight 764.768
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTOLOZANE SULFATE

SMILES

OS([O-])(=O)=O.[H][C@]12SCC(C[N+]3=CC(NC(=O)NCCN)=C(N)N3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC(C)(C)C(O)=O)\C4=NSC(N)=N4)C(O)=O

InChI

InChIKey=UJDQGRLTPBVSFN-TVNHLQOTSA-N
InChI=1S/C23H30N12O8S2.H2O4S/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;1-5(2,3)4/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42);(H2,1,2,3,4)/b31-11-;/t12-,18-;/m1./s1

HIDE SMILES / InChI
Molecular Formula HO4S
Molecular Weight 97.071
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C23H31N12O8S2
Molecular Weight 667.698
Charge 1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

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

Astellas Pharma
23
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

2014
494
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
ZERBAXA

Approved Use

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

Launch Date

2014
Curative
Approved
8429
ZERBAXA

Approved Use

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

Launch Date

2014
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
69.1 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
TAZOBACTAM
 CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
74.4 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
TAZOBACTAM
 CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
172 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
TAZOBACTAM
 CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
182 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
TAZOBACTAM
 CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.77 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
TAZOBACTAM
 CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.12 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
TAZOBACTAM
 CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
81.5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: TAZOBACTAM
TAZOBACTAM
 CEFTOLOZANE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
81.5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
1 g 3 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: TAZOBACTAM
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
Sources:
https://pubmed.ncbi.nlm.nih.gov/20457817
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
Other AEs: Flushing...
Other AEs:
Flushing (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20457817
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
Sources:
https://pubmed.ncbi.nlm.nih.gov/20457817
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
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:
https://pubmed.ncbi.nlm.nih.gov/20457817
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
supressor
21
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2B6
810

CYP2C8
911

CYP2C19
1478

OAT1
599

OAT3
642

OCT1
512

OCT2
647

OATP1B1
788

OATP1B3
706

P-gp
1461

BCRP
699

BSEP
402

MRP2
383

MATE1
306

MATE2
263
P-gp
1537

BCRP
561
CYP
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BCRP
773
 no
BSEP
403
 no
CYP
147
 no
CYP1A2
1692
 no
CYP2B6
1001
 no
CYP2C19
1553
 no
CYP2C8
965
 no
CYP2C9
1819
 no
CYP2D6
1891
 no
MRP2
475
 no
OAT1
603
 no
OATP1B1
803
 no
OCT1
543
 no
OCT2
648
 no
P-gp
1650
 no
MATE1
308
 weak [IC50 >3754 uM]
MATE2
263
 weak [IC50 >3754 uM]
OAT3
644
 weak [IC50 >3754 uM]
OATP1B3
715
 weak [IC50 >3754 uM]
CYP3A4
1925
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
561
 no
P-gp
1537
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
Alsachim
4958
http://www.alsachim.com/product-C6347-glo.bal-view.html
BOC Sciences
689293-68-3
https://www.bocsci.com/ceftolozane-cas-689293-68-3-item-476118.html
BioChemPartner
BCP23708
http://www.biochempartner.com/689293-68-3-BCP23708
ChemShuttle
139011
http://www.chemshuttle.com/catalogsearch/result/?q=689293-68-3&cat=
Chemieliva Pharmaceutical Co., Ltd
PBCM0767804
Clearsynth
CS-CX-00213
https://www.clearsynth.com/en/CSCX00213.html
Compound Cloud
49863420
Compound Cloud
52918380
Compound Cloud
53234134
Google Patents
10725219
https://patents.google.com/?q=JHFNIHVVXRKLEF-VWDPFFEDSA-N
MuseChem
I005927
MuseChem
I005928
ShangHai Biochempartner
BCP23708
Smolecule
S523133
http://www.smolecule.com/products/s523133
THE BioTek
bt-263493
https://www.thebiotek.com/product/inhibitors/bt-263493
ZINC
ZINC000009164421
http://zinc15.docking.org/substances/ZINC000009164421
ZINC
ZINC001850018719
http://zinc15.docking.org/substances/ZINC001850018719
ZINC
ZINC001850018720
http://zinc15.docking.org/substances/ZINC001850018720
ZINC
ZINC001850018721
http://zinc15.docking.org/substances/ZINC001850018721
ZINC
ZINC001850018722
http://zinc15.docking.org/substances/ZINC001850018722
PubMed

PubMed

TitleDatePubMed
Apremilast, a cAMP phosphodiesterase-4 inhibitor, demonstrates anti-inflammatory activity in vitro and in a model of psoriasis.
2010 Feb
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

20140088070
2

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:43:22 GMT 2023
Edited
by admin
on Sat Dec 16 01:43:22 GMT 2023
Record UNII
7R247U84HY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFTOLOZANE SULFATE
MI   USAN   VANDF   WHO-DD  
USAN  
Official Name English
FR-264205
Code English
CEFTOLOZANE SULFATE [USAN]
Common Name English
Ceftolozane sulfate [WHO-DD]
Common Name English
5-AMINO-4-(((2-AMINOETHYL)CARBAMOYL)AMINO)-2-(((6R,7R)-7-(((2Z)-2-(5-AMINO-1,2,4- THIADIAZOL-3-YL)-2-((1-CARBOXY-1-METHYLETHOXY)IMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-1-METHYL-1H-PYRAZOLIUM MONOSULFATE
Systematic Name English
CXA-101
Code English
CEFTOLOZANE SULFATE [MI]
Common Name English
CEFTOLOZANE SULFATE [ORANGE BOOK]
Common Name English
ZERBAXA COMPONENT CEFTOLOZANE SULFATE
Brand Name English
FR264205
Code English
CEFTOLOZANE SULFATE COMPONENT OF ZERBAXA
Brand Name English
CEFTOLOZANE SULFATE [JAN]
Common Name English
CEFTOLOZANE SULFATE [VANDF]
Common Name English
Code System Code Type Description
DAILYMED
7R247U84HY
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
CHEBI
134719
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
EVMPD
SUB167761
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
SMS_ID
100000158129
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
USAN
XX-82
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
CAS
936111-69-2
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
NCI_THESAURUS
C167044
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
PUBCHEM
49863419
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
DRUG BANK
DBSALT001488
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103872
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
RXCUI
1597608
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m3224
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY Merck Index
FDA UNII
7R247U84HY
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID001027693
Created by admin on Sat Dec 16 01:43:22 GMT 2023 , Edited by admin on Sat Dec 16 01:43:22 GMT 2023
PRIMARY
Related Record Type Details
Structure of CEFTOLOZANE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CEFTOLOZANE
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