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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
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 Weight 752.2 g/mol
Molecular Formula C30H34ClN7O10S2
XLogP31
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count15
Rotatable Bond Count12
Exact Mass751.1497103 g/mol
Monoisotopic Mass751.1497103 g/mol
Topological Polar Surface Area310 Ų
Heavy Atom Count50
Formal Charge0
Complexity1440
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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Jinan Tantu Chemicals

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Cefiderocol

About the Company : Jinan Tantu Chemicals Co., Ltd. operates as a Contract Development and Manufacturing Organization (CDMO) that serves pharmaceutical companies worldwide. Our core services include c...

Jinan Tantu Chemicals Co., Ltd. operates as a Contract Development and Manufacturing Organization (CDMO) that serves pharmaceutical companies worldwide. Our core services include customized R&D as well as the production of small molecule pharmaceutical intermediates and Active Pharmaceutical Ingredients (APIs) for both international and domestic pharmaceutical firms. Our capabilities span from laboratory-scale kilograms to commercial ton-scale production. Additionally, we are committed to independent research and development, as well as the production and sales of high-end pharmaceutical intermediates and API products.
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