Cefiderocol

Cefiderocol
Clinical data
Trade namesFetroja, Fetcroja
Other namesRSC-649266
AHFS/Drugs.comMonograph
MedlinePlusa620008
License data
Routes of
administration		Intravenous infusion
Drug classSiderophore cephalosporins
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding56–58%[4]
Elimination half-life2.8 hours
Excretionmainly kidney (60–70% unchanged)
Identifiers
IUPAC name
  • (6R,7R)-7-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-[[1-[2-[(2-chloro-3,4-dihydroxybenzoyl)amino]ethyl]pyrrolidin-1-ium-1-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H34ClN7O10S2
Molar mass752.21 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)(C(=O)O)ON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4(CCCC4)CCNC(=O)C5=C(C(=C(C=C5)O)O)Cl)C(=O)[O-]
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
  • Key:DBPPRLRVDVJOCL-FQRUVTKNSA-N

Cefiderocol, sold under the brand name Fetroja (by Shionogi) among others, is an antibiotic used to treat complicated urinary tract infections when no other options are available.[5] It is indicated for the treatment of multi-drug-resistant Gram-negative bacteria including Pseudomonas aeruginosa.[6][7][8] It is given by injection into a vein.[1]

Common side effects include diarrhea, infusion site reactions, constipation and rash.[9]

Cefiderocol is in the cephalosporin family of medications.[5][10] It was approved for medical use in the United States in November 2019, and in the European Union in April 2020.[5][11][2] In September 2020, cefiderocol (Fetroja) received FDA approval[12] as supplemental New Drug Application (sNDA) for treatment of hospital-acquired bacterial pneumonia (HABP) and ventilator-associated bacterial pneumonia (VABP) when caused by Gram-negative bacteria resistant to other antibiotics. It is on the World Health Organization's List of Essential Medicines.[13]

  1. ^ a b "Fetroja- cefiderocol sulfate tosylate injection, powder, for solution". DailyMed. 19 November 2019. Retrieved 29 April 2020.
  2. ^ a b Cite error: The named reference Fetcroja EPAR was invoked but never defined (see the help page).
  3. ^ "Fetcroja Product information". Union Register of medicinal products. Retrieved 3 March 2023.
  4. ^ Katsube T, Echols R, Arjona Ferreira JC, Krenz HK, Berg JK, Galloway C (May 2017). "Cefiderocol, a Siderophore Cephalosporin for Gram-Negative Bacterial Infections: Pharmacokinetics and Safety in Subjects With Renal Impairment". Journal of Clinical Pharmacology. 57 (5): 584–591. doi:10.1002/jcph.841. PMC 5412848. PMID 27874971.
  5. ^ a b c Cite error: The named reference FDA2019 was invoked but never defined (see the help page).
  6. ^ Choi JJ, McCarthy MW (February 2018). "Cefiderocol: a novel siderophore cephalosporin". Expert Opinion on Investigational Drugs. 27 (2): 193–197. doi:10.1080/13543784.2018.1426745. PMID 29318906. S2CID 205768562.
  7. ^ Aoki T, Yoshizawa H, Yamawaki K, Yokoo K, Sato J, Hisakawa S, et al. (July 2018). "Cefiderocol (S-649266), A new siderophore cephalosporin exhibiting potent activities against Pseudomonas aeruginosa and other gram-negative pathogens including multi-drug resistant bacteria: Structure activity relationship". European Journal of Medicinal Chemistry. 155: 847–868. doi:10.1016/j.ejmech.2018.06.014. PMID 29960205. S2CID 49682995.
  8. ^ Portsmouth S, van Veenhuyzen D, Echols R, Machida M, Ferreira JC, Ariyasu M, et al. (December 2018). "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". The Lancet. Infectious Diseases. 18 (12): 1319–1328. doi:10.1016/S1473-3099(18)30554-1. PMID 30509675. S2CID 54552812.
  9. ^ "Drug Trials Snapshot: Fetroja". U.S. Food and Drug Administration (FDA). 14 November 2019. Retrieved 29 April 2020. This article incorporates text from this source, which is in the public domain.
  10. ^ Zhanel GG, Golden AR, Zelenitsky S, Wiebe K, Lawrence CK, Adam HJ, et al. (February 2019). "Cefiderocol: A Siderophore Cephalosporin with Activity Against Carbapenem-Resistant and Multidrug-Resistant Gram-Negative Bacilli". Drugs. 79 (3): 271–289. doi:10.1007/s40265-019-1055-2. PMID 30712199. S2CID 59541210.
  11. ^ "Drug Approval Package: Fetroja (cefiderocol)". U.S. Food and Drug Administration (FDA). 19 December 2019. Retrieved 29 April 2020.
  12. ^ "FDA Approves Fetroja (cefiderocol) for the Treatment of Hospital-acquired Bacterial Pneumonia and Ventilator-associated Bacterial Pneumonia". Drugs.com. Retrieved 29 September 2020.
  13. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
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