CEFTOLOZANE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H30N12O8S2
Molecular Weight	666.69
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

[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=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

Molecular Formula	C23H30N12O8S2
Molecular Weight	666.69
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intra-abdominal infections 49	Curative		Approved 8,429	ZERBAXA
Pyelonephritis 5	Curative		Approved 8,429	ZERBAXA

C_max

Value	Dose	Co-administered	Analyte	Population
69.1 μg/mL	1 g single, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens
74.4 μg/mL	1 g 3 times / day steady-state, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
172 μg × h/mL	1 g single, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens
182 μg × h/mL	1 g 3 times / day steady-state, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.77 h	1 g single, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens
3.12 h	1 g 3 times / day steady-state, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
81.5%	1 g single, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens
81.5%	1 g 3 times / day steady-state, intravenous	TAZOBACTAM	CEFTOLOZANE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
2000 mg single, intravenous Highest studied dose	healthy, 29.5 years (range: 19–59 years) n = 6
1000 mg 3 times / day steady, intravenous Highest studied dose	healthy, 33.0 years (range: 22–55 years) n = 6	Other AEs: Flushing...
1500 mg 2 times / day steady, intravenous Highest studied dose	healthy, 33.0 years (range: 22–55 years) n = 6

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AEs

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AE	Significance	Dose	Population
Flushing	1 patient	1000 mg 3 times / day steady, intravenous Highest studied dose	healthy, 33.0 years (range: 22–55 years) n = 6

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
supressor 21	inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 810 CYP2C8 911 CYP2C19 1,478 OAT1 599 OAT3 642 OCT1 512 OCT2 647 OATP1B1 788 OATP1B3 706 P-gp 1,461 BCRP 699 BSEP 402 MRP2 383 MATE1 306 MATE2 263	P-gp 1,537 BCRP 561	CYP 76

Drug as perpetrator

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Target	Modality	Activity
BCRP 773	inhibitor 3,277	no
BSEP 403	inhibitor 3,277	no
CYP 147	inducer 1,573	no
CYP1A2 1,692	supressor 155	no
CYP2B6 1,001	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 561	substrate 3,367	no
P-gp 1,537	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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

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PubMed

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Title	Date	PubMed
Apremilast, a cAMP phosphodiesterase-4 inhibitor, demonstrates anti-inflammatory activity in vitro and in a model of psoriasis.	2010 Feb	20050849
Ceftolozane/Tazobactam: a new option in the treatment of complicated gram-negative infections.	2014 Dec	25516692
Ceftolozane/tazobactam: a novel cephalosporin/β-lactamase inhibitor combination with activity against multidrug-resistant gram-negative bacilli.	2014 Jan	24352909

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Patents

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
Record UNII	37A4IES95Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFTOLOZANE

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

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Code System

Code