Identification

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Name
Cefiderocol
Accession Number
DB14879
Type
Small Molecule
Groups
Approved, Investigational
Description

Cefiderocol is a cephalosporin antibacterial drug and exerts a mechanism of action similar to other β-lactam antibiotics.Label Unlike other agents in this category, cefiderocol is a siderophore able to undergo active transport into the bacterial cell through iron channels.2 It represents a significant addition to antibacterial treatment option as it has proven to be effective in vitro against multidrug resistant strains including extended spectrum β-lactamase producers and carbapenemase producing bacteria.

Cefiderocol was granted designation as a Qualified Infectious Disease Product and granted priority review status by the FDA on November 14, 2019.7 It is indicated for use in complicated urinary tract infections in patients with limited or no alternative treatments available.Label This indication was supported by a positive clinical trial composed of 448 patients with complicated urinary tract infections which demonstrated a 72.6% rate of symptom resolution and bacterial eradication with cefiderocol compared to 54.6% with the comparator, imipenem/cilastatin.4 A concern noted in the trial was a 0.3% higher rate of all cause mortality, the cause of which has not been determined.

Structure
Thumb
Synonyms
  • Cefiderocol
External IDs
RSC 649266 / S 649266 / S-649266
Product Ingredients
IngredientUNIICASInChI Key
Cefiderocol sulfate tosylateTTP8LBP45D2135543-94-9QNMVZYPDWLKAJC-RXVBEKIDSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FetrojaInjection, powder, for solution1 g/10mLIntravenousSHIONOGI INC.2020-01-31Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
SZ34OMG6E8
CAS number
1225208-94-5
Weight
Average: 752.21
Monoisotopic: 751.1497104
Chemical Formula
C30H34ClN7O10S2
InChI Key
DBPPRLRVDVJOCL-FQRUVTKNSA-N
InChI
InChI=1S/C30H34ClN7O10S2/c1-30(2,28(46)47)48-36-19(16-13-50-29(32)34-16)24(42)35-20-25(43)37-21(27(44)45)14(12-49-26(20)37)11-38(8-3-4-9-38)10-7-33-23(41)15-5-6-17(39)22(40)18(15)31/h5-6,13,20,26H,3-4,7-12H2,1-2H3,(H7-,32,33,34,35,36,39,40,41,42,44,45,46,47)/t20-,26-/m1/s1
IUPAC Name
1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-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}-1-{2-[(2-chloro-3,4-dihydroxyphenyl)formamido]ethyl}pyrrolidin-1-ium
SMILES
[H][C@]12SCC(C[N+]3(CCNC(=O)C4=C(Cl)C(O)=C(O)C=C4)CCCC3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC(N)=N1)C([O-])=O

Pharmacology

Indication

Cefiderocol is indicated for the treatment of complicated urinary tract infections with or without pyelonephritis.Label

Associated Conditions
Pharmacodynamics

Similarly to other cephalosporins, cefiderocol exerts bactericidal activity against a range of bacterial species.Label,2 Cefiderocol has primarily shown efficacy against aerobic Gram negative bacteria including Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa.2

Mechanism of action

Cefiderocol acts by binding to and inhibiting penicillin-binding proteins (PBPs), preventing cell wall synthesis and ultimately causing death of the bacterial cell.Label,2 Like other β-lactam antibiotics cefiderocol is able to enter bacterial cells via passive diffusion through porins.3,Label Unlike other β-lactams, cefiderocol contains a chlorocatechol group which allows it to chelate iron. Once bound to ferric iron cefiderocol is able to undergo active transport into bacterial cells through iron channels in the outer cell membrane such as those encoded by the cirA and fiu genes in E. coli or the PiuA gene in P. aeruginosa. Once inside the cell, cefiderocol binds to and inhibits PBP3 with high affinity thereby preventing the linking of peptodoglycan layers via the pentapeptide bridge.Label,2,5 PBP1a, 1b, 2,and 4 are also bound and inhibited by cefiderocol but with a lesser potency than PBP3 and are therefore expected to contribute less to its antibacterial effect.

TargetActionsOrganism
APenicillin-binding protein 3
inhibitor
Pseudomonas aeruginosa
APenicillin-binding protein 1A
inhibitor
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
APenicillin-binding protein 1B
inhibitor
Pseudomonas aeruginosa
APenicillin-binding protein 2
inhibitor
Pseudomonas aeruginosa
AD-alanyl-D-alanine carboxypeptidase DacB
inhibitor
Escherichia coli (strain K12)
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

A single intravenous dose of 2 g of cefiderocol in healthy patients produces a Cmax of 89.7 mg/L and an AUC of 386 mg*h/L.Label In patients with complicated urinary tract infections and a creatinine clearance of at least 60 mL/min, doses of 2 g cefiderocol every 8 hours produced an AUC of 394.7 mg*h/L and a Cmax of 138 mg/L. However the infusion rate for this chronic dosing was 3 times the recommended rate. Cmax and AUC are known to increase proportionally with dosage.

Volume of distribution

Cefiderocol has a mean volume of distribution of 18 L.Label

Protein binding

Cefiderocol is 40-60% bound to plasma proteins, predominantly to albumin.Label

Metabolism

Cefiderocol undergoes a small degree of metabolism to a cefiderocol epimer at the 7 position, cefiderocol catechol-3-methoxy and -4-methoxy, and a pyrrolidine chlorobenzamide product (PCBA).1 PCBA undergoes further metabolism to sulfated, methylated, and glucuronidated metabolites. The enzymes involved in these reactions have yet to be identified and cefiderocol has not been shown to interfere in the metabolism of other agents.Label

Route of elimination

98.6% of cefiderocol is eliminated in the urine with 90.6% as the unchanged parent drug.Label The remaining 8% is eliminated as metabolites. 2.8% is eliminated in the feces. Less than 10% of cefiderocol is metabolized.

Half life

The terminal elimination half-life of cefiderocol is 2-3 h.Label

Clearance

Cefiderocol has a mean clearance of 5.18 L/h.Label

Toxicity

Information on cefiderocol toxicity is not yet available. In case of overdose supportive care is recommended.Label Hemodialysis has proven effective in removing cefiderocol with a 3-4 hour session removing 60% of circulating drug.

Affected organisms
  • Pseudomonas aeruginosa
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Neisseria gonorrhoeae
  • Campylobacter jejuni
  • Escherichia coli
  • Salmonella typhi
  • Moraxella catarrhalis
  • Serratia marcescens
  • Proteus vulgaris
  • Proteus mirabilis
  • Providencia stuartii
  • Providencia rettgeri
  • Morganella morganii
  • Enterobacter cloacae
  • Klebsiella pneumoniae
  • Klebsiella oxytoca
  • Salmonella paratyphi
  • Shigella flexneri
  • Pseudomonas putida
  • Citrobacter freundii
  • Yersinia enterocolitica
  • Pseudomonas stutzeri
  • Acinetobacter calcoaceticus
  • Salmonella typhimurium
  • Micrococcus luteus
  • Salmonella enteritidis
  • Aeromonas hydrophila
  • Acinetobacter baumannii
  • Elizabethkingia meningoseptica
  • Stenotrophomonas maltophilia
  • Acinetobacter johnsonii
  • Acinetobacter haemolyticus
  • Acinetobacter lwoffii
  • Salmonella choleraesuis
  • Vibrio fluvialis
  • Vibrio vulnificus
  • Yersinia pseudotuberculosis
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.
Not Available
Food Interactions
Not Available

References

General References
  1. Miyazaki S, Katsube T, Shen H, Tomek C, Narukawa Y: Metabolism, Excretion, and Pharmacokinetics of [(14) C]-Cefiderocol (S-649266), a Siderophore Cephalosporin, in Healthy Subjects Following Intravenous Administration. J Clin Pharmacol. 2019 Jul;59(7):958-967. doi: 10.1002/jcph.1386. Epub 2019 Feb 7. [PubMed:30730562]
  2. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
  3. Kobayashi Y, Takahashi I, Nakae T: Diffusion of beta-lactam antibiotics through liposome membranes containing purified porins. Antimicrob Agents Chemother. 1982 Nov;22(5):775-80. doi: 10.1128/aac.22.5.775. [PubMed:6295267]
  4. Portsmouth S, van Veenhuyzen D, Echols R, Machida M, Ferreira JCA, Ariyasu M, Tenke P, Nagata TD: Cefiderocol versus imipenem-cilastatin for the treatment of complicated urinary tract infections caused by Gram-negative uropathogens: a phase 2, randomised, double-blind, non-inferiority trial. Lancet Infect Dis. 2018 Dec;18(12):1319-1328. doi: 10.1016/S1473-3099(18)30554-1. Epub 2018 Oct 25. [PubMed:30509675]
  5. Brunton LL, Hilal-Dandan R, Knollmann BC. eds (2018). Goodman & Gilman's: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [ISBN:978-1-25-958473-2]
  6. ChemSpider: Cefiderocol [Link]
  7. FDA Press Release Cefiderocol [Link]
External Links
ChemSpider
52084902
RxNav
2265702
ChEMBL
CHEMBL3989974
Wikipedia
Cefiderocol
FDA label
Download (387 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentPneumonia, Bacterial1
2CompletedTreatmentUrinary Tract Infection1
2RecruitingTreatmentBloodstream Infections1
2RecruitingTreatmentComplicated Urinary Tract Infection / Gram-Negative Bacterial Infections1
3Active Not RecruitingTreatmentBloodstream Infections (BSI) / Complicated Urinary Tract Infection / Healthcare-associated Pneumonia (HCAP) / Nosocomial Pneumonia / Sepsis / Ventilator-associated Bacterial Pneumonia1
3CompletedTreatmentHealthcare-associated Pneumonia (HCAP) / Nosocomial Pneumonia / Ventilator-associated Bacterial Pneumonia1
Not AvailableAvailableNot AvailableBacterial Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntravenous1 g/10mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US9238657No2016-01-192031-11-19Us
US10004750No2018-06-262035-09-03Us
US9949982No2018-04-242035-09-03Us
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-2.265ChemSpider: Cefiderocol
Predicted Properties
PropertyValueSource
Water Solubility0.00201 mg/mLALOGPS
logP1.84ALOGPS
logP-2.9ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)2.64ChemAxon
pKa (Strongest Basic)4.05ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area256.9 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity204.1 m3·mol-1ChemAxon
Polarizability72.74 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Known to bind to PBP3 of E. coli NIHJ JC-2, K. pneumoniae SR22291, P. aeruginosa ATCC 27853, and A. baumannii ATCC 17978.
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. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Known to bind to PBP1a of E. coli NIHJ JC-2, K. pneumoniae SR22291, and P. aeruginosa ATCC 27853. May bind to either PBP1a, PBP1b or both of A. baumannii ATCC 17978.
General Function
Transferase activity, transferring glycosyl groups
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
mrcA
Uniprot ID
Q07806
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
91198.715 Da
References
  1. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Known to bind to PBP1b of E. coli NIHJ JC-2, K. pneumoniae SR22291, and P. aeruginosa ATCC 27853. May bind to either PBP1a, PBP1b or both of A. baumannii ATCC 17978.
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. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Known to bind to PBP3 of E. coli NIHJ JC-2, K. pneumoniae SR22291, and P. aeruginosa ATCC 27853, and A. baumannii ATCC 17978.
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
pbpA
Uniprot ID
Q9X6V3
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
72212.855 Da
References
  1. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Known to bind to PBP4 of E. coli NIHJ JC-2, K. pneumoniae SR22291, and P. aeruginosa ATCC 27853.
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Gene Name
dacB
Uniprot ID
P24228
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacB
Molecular Weight
51797.85 Da
References
  1. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Ligand
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Transporters

Kind
Protein group
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
No
Actions
Substrate
General Function
Drug transmembrane transporter activity
Specific Function
The periplasmic linker component of the MexAB-OprM efflux system that confers multidrug resistance. Also functions as the major efflux pump for n-hexane and p-xylene efflux. Over-expression of the ...

Components:
References
  1. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
No
Actions
Substrate
Curator comments
Cefiderocol acts as a substrate when bound to iron.
General Function
Involved in the active transport across the outer membrane of iron complexed with catecholate siderophores such as dihydroxybenzoylserine and dihydroxybenzoate. It derives its energy for transport by interacting with the trans-periplasmic membrane protein TonB. Can also transport catechol-substituted cephalosporins. Receptor for microcins M, H47 and E492.
Specific Function
Siderophore uptake transmembrane transporter activity
Gene Name
fiu
Uniprot ID
P75780
Uniprot Name
Catecholate siderophore receptor Fiu
Molecular Weight
81959.515 Da
References
  1. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
No
Actions
Substrate
Curator comments
Cefiderocol acts as a substrate when bound to iron.
General Function
Siderophore transmembrane transporter activity
Specific Function
Not yet known. Postulated to participate in iron transport. Outer membrane receptor for colicins IA and IB.
Gene Name
cirA
Uniprot ID
P17315
Uniprot Name
Colicin I receptor
Molecular Weight
73895.2 Da
References
  1. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain UCBPP-PA14)
Pharmacological action
No
Actions
Substrate
Curator comments
Cefiderocol acts as a substrate when bound to iron.
General Function
Not Available
Specific Function
Siderophore uptake transmembrane transporter activity
Gene Name
piuA
Uniprot ID
A0A0H2ZGX7
Uniprot Name
Putative outer membrane ferric siderophore receptor
Molecular Weight
82344.98 Da
References
  1. Ito A, Sato T, Ota M, Takemura M, Nishikawa T, Toba S, Kohira N, Miyagawa S, Ishibashi N, Matsumoto S, Nakamura R, Tsuji M, Yamano Y: In Vitro Antibacterial Properties of Cefiderocol, a Novel Siderophore Cephalosporin, against Gram-Negative Bacteria. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: AAC.01454-17. doi: 10.1128/AAC.01454-17. Print 2018 Jan. [PubMed:29061741]

Drug created on May 20, 2019 08:32 / Updated on February 02, 2020 04:36