cefiderocol   Click here for help

GtoPdb Ligand ID: 10776

Synonyms: compound 3 [PMID: 29960205] | Fetcroja® | Fetroja® | GSK-2696266 | GSK2696266 | RSC 649266 | RSC-649266 | RSC649266 | S-649266
Approved drug
cefiderocol is an approved drug (FDA (2019), EMA (2020))
Compound class: Synthetic organic
Comment: Cefiderocol (S-649266) is a novel parenteral cephalosporin antibacterial with Gram-negative activity including against multi-drug resistant bacteria [1,3]. Chemically it is a catechol-conjugated siderophore cephalosporin. It was developed to treat bloodstream infections, hospital-acquired and ventilator-associated bacterial pneumonia, and complicated urinary tract infections. It can be formulated as the sulphate tosylate complex. Cefiderocol was the first siderophore class antibacterial to be approved by FDA.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 15
Topological polar surface area 310.44
Molecular weight 751.15
XLogP -1.85
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1[C@@H](NC(=O)/C(=N\OC(C(=O)O)(C)C)/c2csc(n2)N)[C@@H]2N1C(=C(CS2)C[N+]1(CCCC1)CCNC(=O)c1ccc(c(c1Cl)O)O)C(=O)[O-]
Isomeric SMILES O=C1[C@@H](NC(=O)/C(=N\OC(C(=O)O)(C)C)/c2csc(n2)N)[C@@H]2N1C(=C(CS2)C[N+]1(CCCC1)CCNC(=O)c1ccc(c(c1Cl)O)O)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
InChI Key DBPPRLRVDVJOCL-FQRUVTKNSA-N
No information available.
Summary of Clinical Use Click here for help
In November 2019 the FDA approved cefiderocol as a treatment for urinary tract infections caused by multi-drug-resistant Gram -ve bacteria including Pseudomonas aeruginosa, when few or no other treatment options are available. It is under evaluation for authorisation by the EMA (last updated April 29, 2020).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02321800 A Study of Efficacy and Safety of Intravenous Cefiderocol (S-649266) Versus Imipenem/Cilastatin in Complicated Urinary Tract Infections Phase 2 Interventional Shionogi Inc. 2
NCT02714595 Study of S-649266 or Best Available Therapy for the Treatment of Severe Infections Caused by Carbapenem-resistant Gram-negative Pathogens Phase 3 Interventional Shionogi Inc. 2
NCT03780140 Expanded Access to Cefiderocol for the Intravenous Treatment of Severe Gram Negative Bacterial Infections Expanded Access Shionogi Inc. 2
External links Click here for help
For extended ADME data see the following:

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