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
References
1. Aoki T, Yoshizawa H, Yamawaki K, Yokoo K, Sato J, Hisakawa S, Hasegawa Y, Kusano H, Sano M, Sugimoto H et al.. (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.
Eur J Med Chem, 155: 847-868. [PMID:29960205]
2. Portsmouth S, van Veenhuyzen D, Echols R, Machida M, Ferreira JCA, Ariyasu M, Tenke P, Nagata TD. (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.
Lancet Infect Dis, 18 (12): 1319-1328. [PMID:30509675]
3. Sato T, Yamawaki K. (2019)
Cefiderocol: Discovery, Chemistry, and In Vivo Profiles of a Novel Siderophore Cephalosporin.
Clin Infect Dis, 69 (Supplement_7): S538-S543. [PMID:31724047]