Cefiderocol

  • CAT Number: I004918
  • CAS Number: 1225208-94-5
  • Molecular Formula: C30H34ClN7O10S2
  • Molecular Weight: 752.211
  • Purity: ≥95%
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Cefiderocol (CAT: I004918) is a novel cephalosporin antibiotic with a unique mechanism of action. It belongs to the category of siderophore cephalosporins and acts by utilizing iron transport systems to enter bacterial cells. Cefiderocol exhibits potent activity against Gram-negative pathogens, including multidrug-resistant strains such as carbapenem-resistant Enterobacteriaceae (CRE) and extensively drug-resistant Pseudomonas aeruginosa. By binding to penicillin-binding proteins and inhibiting cell wall synthesis, cefiderocol effectively kills bacteria. It has demonstrated efficacy in treating complicated urinary tract infections, hospital-acquired pneumonia, and bloodstream infections caused by difficult-to-treat Gram-negative bacteria.

Catalog Number I004918
CAS Number 1225208-94-5
Synonyms

S-649266; S 649266; S649266; Cefiderocol;(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetamido]-3-({1-[2-(2-chloro-3,4-dihydroxybenzamido)ethyl]pyrrolidin-1-ium-1-yl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-e

Molecular Formula

C30H34ClN7O10S2

Purity 95%
Solubility Soluble in DMSO, not in water
Storage 0 - 4 °C for short term or -20 °C for long term
Overview of Clinical Research

<span style=”color:#000000;”><span style=”font-size:12px;”><span style=”font-family:arial,helvetica,sans-serif;”>Cefiderocol is a cell wall inhibitor. The antimicrobial data from the phase III APEKS-NP trial in Gram-negative infections presented at the IDWeek 2020.</span></span></span>

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
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
InChIKey DBPPRLRVDVJOCL-FQRUVTKNSA-N
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-]
Reference

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1:Susceptibility of imipenem-susceptible but meropenem-resistant Enterobacteriaceae carrying <i>bla</i><sub>IMP-6</sub> to various antibacterials including siderophore cephalosporin, cefiderocol. Kanazawa S, Sato T, Kohira N, Ito-Horiyama T, Tsuji M, Yamano Y.Antimicrob Agents Chemother. 2017 Apr 24. pii: AAC.00576-17. doi: 10.1128/AAC.00576-17. [Epub ahead of print] PMID: 28438934<br />
2:Cefiderocol MIC quality control ranges in iron-depleted cation-adjusted Mueller-Hinton broth using a CLSI M23-A4 multi-laboratory study design. Huband MD, Ito A, Tsuji M, Sader HS, Fedler KA, Flamm RK.Diagn Microbiol Infect Dis. 2017 Jun;88(2):198-200. doi: 10.1016/j.diagmicrobio.2017.03.011. Epub 2017 Mar 23. PMID: 28410852<br />
3:Activity of cefiderocol (S-649266) against carbapenem-resistant Gram-negative bacteria collected from inpatients in Greek hospitals. Falagas ME, Skalidis T, Vardakas KZ, Legakis NJ; Hellenic Cefiderocol Study Group..J Antimicrob Chemother. 2017 Mar 22. doi: 10.1093/jac/dkx049. [Epub ahead of print] PMID: 28369471<br />
4:Cefiderocol, a Siderophore Cephalosporin for Gram-Negative Bacterial Infections: Pharmacokinetics and Safety in Subjects With Renal Impairment. Katsube T, Echols R, Arjona Ferreira JC, Krenz HK, Berg JK, Galloway C.J Clin Pharmacol. 2017 May;57(5):584-591. doi: 10.1002/jcph.841. Epub 2016 Nov 22. PMID: 27874971 Free PMC Article<br />
5:Pharmacokinetic/Pharmacodynamic Modeling and Simulation of Cefiderocol, a Parenteral Siderophore Cephalosporin, for Dose Adjustment Based on Renal Function. Katsube T, Wajima T, Ishibashi T, Arjona Ferreira JC, Echols R.Antimicrob Agents Chemother. 2016 Dec 27;61(1). pii: e01381-16. doi: 10.1128/AAC.01381-16. Print 2017 Jan. PMID: 27795374<br />
6:Siderophore Cephalosporin Cefiderocol Utilizes Ferric Iron Transporter Systems for Antibacterial Activity against Pseudomonas aeruginosa. Ito A, Nishikawa T, Matsumoto S, Yoshizawa H, Sato T, Nakamura R, Tsuji M, Yamano Y.Antimicrob Agents Chemother. 2016 Nov 21;60(12):7396-7401. Print 2016 Dec. PMID: 27736756 Free PMC Article

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