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Also known as: 1225208-94-5, Cefiderocol [inn], Gsk2696266, Cefiderocol [who-dd], Sz34omg6e8, S-649266

Molecular Formula

C₃₀H₃₄ClN₇O₁₀S₂

Molecular Weight

752.2 g/mol

InChI Key

DBPPRLRVDVJOCL-FQRUVTKNSA-N

FDA UNII

SZ34OMG6E8

Cefiderocol is a cephalosporin antibacterial drug and exerts a mechanism of action similar to other -lactam antibiotics. Unlike other agents in this category, cefiderocol is a siderophore able to undergo active transport into the bacterial cell through iron channels. It represents a significant addition to antibacterial treatment option as it has proven to be effective *in vitro* against multidrug resistant strains including extended spectrum -lactamase producers and carbapenemase producing bacteria. Cefiderocol was granted designation as a Qualified Infectious Disease Product and granted priority review status by the FDA on November 14, 2019. It is indicated for use in complicated urinary tract infections in patients with limited or no alternative treatments available. This indication was supported by a positive clinical trial composed of 448 patients with complicated urinary tract infections which demonstrated a 72.6% rate of symptom resolution and bacterial eradication with cefiderocol compared to 54.6% with the comparator, imipenem/cilastatin. A concern noted in the trial was a 0.3% higher rate of all cause mortality, the cause of which has not been determined.

Cefiderocol is a Cephalosporin Antibacterial.

1 2D Structure

Cefiderocol

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

DBPPRLRVDVJOCL-FQRUVTKNSA-N

2.1.4 Canonical 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-]

2.1.5 Isomeric SMILES

CC(C)(C(=O)O)O/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4(CCCC4)CCNC(=O)C5=C(C(=C(C=C5)O)O)Cl)C(=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

SZ34OMG6E8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. S-649266

2.3.2 Depositor-Supplied Synonyms

1. 1225208-94-5

2. Cefiderocol [inn]

3. Gsk2696266

4. Cefiderocol [who-dd]

5. Sz34omg6e8

6. S-649266

7. Cefiderocol (usan)

8. Cefiderocol [usan]

9. (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

10. Pyrrolidinium, 1-(((6r,7r)-7-(((2z)-2-(2-amino-4-thiazolyl)-2-((1-carboxy-1-methylethoxy)imino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-1-(2-((2-chloro-3,4-dihydroxybenzoyl)amino)ethyl)-, Inner Salt

11. Rsc 649266

12. Pyrrolidinium, 1-[[(6r,7r)-7-[[(2z)-2-(2-amino-4-thiazolyl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-[2-[(2-chloro-3,4-dihydroxybenzoyl)amino]ethyl]-, Inner Salt

13. Cefiderocol [mi]

14. Cefiderocol [usan:inn]

15. Unii-sz34omg6e8

16. Chembl3989974

17. Schembl22508010

18. Dtxsid401098052

19. Akos037648584

20. Db14879

21. Gsk 2696266

22. Bs-14716

23. Hy-17628

24. Cs-0016784

25. D11302

26. S 649266

27. (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-ene-2-carboxylate

2.4 Create Date

2014-09-22

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₃₄ClN₇O₁₀S₂
Molecular Weight	752.2 g/mol
XLogP3	1
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	12
Exact Mass	751.1497103 g/mol
Monoisotopic Mass	751.1497103 g/mol
Topological Polar Surface Area	310 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	1440
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Cefiderocol is indicated for the treatment of complicated urinary tract infections with or without pyelonephritis.

FDA Label

Fetcroja is indicated for the treatment of infections due to aerobic Gram-negative organisms in adults with limited treatment options (see sections 4. 2, 4. 4 and 5. 1).

Consideration should be given to official guidance on the appropriate use of antibacterial agents.

Treatment of infections due to aerobic Gram-negative bacteria

5 Pharmacology and Biochemistry

5.1 Pharmacology

Similarly to other cephalosporins, cefiderocol exerts bactericidal activity against a range of bacterial species. Cefiderocol has primarily shown efficacy against aerobic Gram negative bacteria including *Escherichia coli*, *Klebsiella pneumoniae*, and *Pseudomonas aeruginosa*.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

CEFIDEROCOL

5.2.2 FDA UNII

SZ34OMG6E8

5.2.3 Pharmacological Classes

Chemical Structure [CS] - Cephalosporins

5.3 ATC Code

J01D

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DI - Other cephalosporins and penems

J01DI04 - Cefiderocol

5.4 Absorption, Distribution and Excretion

Absorption

A single intravenous dose of 2 g of cefiderocol in healthy patients produces a Cmax of 89.7 mg/L and an AUC of 386 mg\*h/L. In patients with complicated urinary tract infections and a creatinine clearance of at least 60 mL/min, doses of 2 g cefiderocol every 8 hours produced an AUC of 394.7 mg*h/L and a Cmax of 138 mg/L. However the infusion rate for this chronic dosing was 3 times the recommended rate. Cmax and AUC are known to increase proportionally with dosage.

Route of Elimination

98.6% of cefiderocol is eliminated in the urine with 90.6% as the unchanged parent drug. The remaining 8% is eliminated as metabolites. 2.8% is eliminated in the feces. Less than 10% of cefiderocol is metabolized.

Volume of Distribution

Cefiderocol has a mean volume of distribution of 18 L.

Clearance

Cefiderocol has a mean clearance of 5.18 L/h.

5.5 Metabolism/Metabolites

Cefiderocol undergoes a small degree of metabolism to a cefiderocol epimer at the 7 position, cefiderocol catechol-3-methoxy and -4-methoxy, and a pyrrolidine chlorobenzamide product (PCBA). PCBA undergoes further metabolism to sulfated, methylated, and glucuronidated metabolites. The enzymes involved in these reactions have yet to be identified and cefiderocol has not been shown to interfere in the metabolism of other agents.

5.6 Biological Half-Life

The terminal elimination half-life of cefiderocol is 2-3 h.

5.7 Mechanism of Action

Cefiderocol acts by binding to and inhibiting penicillin-binding proteins (PBPs), preventing cell wall synthesis and ultimately causing death of the bacterial cell. Like other -lactam antibiotics cefiderocol is able to enter bacterial cells via passive diffusion through porins. Unlike other -lactams, cefiderocol contains a chlorocatechol group which allows it to chelate iron. Once bound to ferric iron cefiderocol is able to undergo active transport into bacterial cells through iron channels in the outer cell membrane such as those encoded by the *cirA* and *fiu* genes in *E. coli* or the *PiuA* gene in *P. aeruginosa*. Once inside the cell, cefiderocol binds to and inhibits PBP3 with high affinity thereby preventing the linking of peptodoglycan layers via the pentapeptide bridge. PBP1a, 1b, 2,and 4 are also bound and inhibited by cefiderocol but with a lesser potency than PBP3 and are therefore expected to contribute less to its antibacterial effect.

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