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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2019), EMA (2020))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
10234 cefiderocol
Synonyms Click here for help
compound 3 [PMID: 29960205] | Fetcroja® | Fetroja® | GSK-2696266 | GSK2696266 | RSC 649266 | RSC-649266 | RSC649266 | S-649266
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefiderocol (S-649266; GSK-2696266; RSC 649266)
Other databases
CAS Registry No. 1225208-94-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL3989974
DrugCentral Ligand 5352
GtoPdb PubChem SID 405560217
PubChem CID 77843966
Search Google for chemical match using the InChIKey DBPPRLRVDVJOCL-FQRUVTKNSA-N
Search Google for chemicals with the same backbone DBPPRLRVDVJOCL
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UniChem Compound Search for chemical match using the InChIKey DBPPRLRVDVJOCL-FQRUVTKNSA-N
UniChem Connectivity Search for chemical match using the InChIKey DBPPRLRVDVJOCL-FQRUVTKNSA-N