Cefiderocol free base | CAS#1225208-94-5 (free base) | cephalosporin antibiotic

MedKoo Cat#: 319576 | Name: Cefiderocol free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cefiderocol (free base), also known as S-649266, is a potent siderophore cephalosporin antibiotic with a catechol moiety on the 3-position side chain. S-649266 shows potent in vitro activity against the non-fermenting Gram-negative bacteria Acinetobacter baumannii, Pseudomonas aeruginosa and Stenotrophomonas maltophilia, including MDR strains such as carbapenem-resistant A. baumannii and metallo-β-lactamase-producing P. aeruginosa. S-649266 showed potent in vitro activities against A. baumannii producing carbapenemases such as OXA-type β-lactamases, and P. aeruginosa producing metallo-β-lactamases such as IMP type and VIM type. FDA approved this drug in 11/14/2019 To treat patients with complicated urinary tract infections who have limited or no alternative treatment options

Chemical Structure

Cefiderocol free base

CAS#1225208-94-5 (free base)

Theoretical Analysis

MedKoo Cat#: 319576

Name: Cefiderocol free base

CAS#: 1225208-94-5 (free base)

Chemical Formula: C30H34ClN7O10S2

Exact Mass: 751.1497

Molecular Weight: 752.21

Elemental Analysis: C, 47.90; H, 4.56; Cl, 4.71; N, 13.03; O, 21.27; S, 8.52

Price and Availability

Size	Price	Availability
1mg	USD 190.00	Ready to ship
5mg	USD 550.00	Ready to ship
10mg	USD 950.00	Ready to ship
25mg	USD 2,050.00	Ready to ship
50mg	USD 3,650.00	Ready to ship
100mg	USD 5,850.00	Ready to ship

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Related CAS #

1883830-01-0 (ditosylate hydrate) 1225208-94-5 (free base) 2009350-94-9 (sulfate tosylate) 2135543-94-9 (sulfate tosylate hydrate)

Synonym

S-649266; S 649266; S649266; GSK2696266D; GSK-2696266D; GSK 2696266D; S-649266D; S 649266D; S649266D; Cefiderocol; Fetroja.

IUPAC/Chemical Name

(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

InChi Key

DBPPRLRVDVJOCL-FQRUVTKNSA-N

InChi Code

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

SMILES Code

OC(C(O)=C1Cl)=CC=C1C(NCC[N+]2(CCCC2)CC3=C(C([O-])=O)N4C([C@H]([C@]4(SC3)[H])NC(/C(C5=CSC(N)=N5)=N\OC(C(O)=O)(C)C)=O)=O)=O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis5

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

S-649266 shows potent in vitro activity against the non-fermenting Gram-negative bacteria Acinetobacter baumannii, Pseudomonas aeruginosa and Stenotrophomonas maltophilia, including MDR strains such as carbapenem-resistant A. baumannii and metallo-β-lactamase-producing P. aeruginosa. MIC90s of S-649266 for A. baumannii, P. aeruginosa and S. maltophilia were 2, 1 and 0.5 mg/L, respectively, whereas MIC90s of meropenem were >16 mg/L. S-649266 showed potent in vitro activities against A. baumannii producing carbapenemases such as OXA-type β-lactamases, and P. aeruginosa producing metallo-β-lactamases such as IMP type and VIM type. MIC90 values for these A. baumannii strains and P. aeruginosa strains were 8 and 4 mg/L, respectively.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A8T09K18

QC Data

View QC data: current batch, Lot#A8T09K18

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Cefiderocol (S-649266) is a siderophore cephalosporin which has a potent activity against a broad range of aerobic Gram-negative bacterial species with MIC50s of 2 μg/mL or less.

In vitro activity:

Cefiderocol demonstrated potent in vitro activity against a wide range of Gram-negative pathogens, including meropenem-resistant strains, from multiple infection sources. Susceptibility rates for cefiderocol against non-fermenters, including A. baumannii, were high (>95%). Cefiderocol represents a promising alternative treatment option for clinicians in the fight against antimicrobial-resistant Gram-negative bacilli, especially in areas where carbapenem resistance and MBL-producing strains are prevalent. Reference: J Glob Antimicrob Resist. 2021 May 18;25:390-398. https://www.sciencedirect.com/science/article/pii/S2213716521001181?via%3Dihub

In vivo activity:

In this rat model, the lungs of untreated animals showed hemorrhagic inflammation and a 1-log10 CFU/lung increase in bacterial numbers over 96 h. Against both strains of S. maltophilia, humanized cefiderocol dosing reduced the viable cell count by 2- to 3-log10 CFU/lung compared with baseline controls, which received no intervention (Fig. 4). This suggests that cefiderocol administered according to the approved dosing regimen has the clinical potential to effectively treat respiratory tract infections caused by S. maltophilia. Reference: Antimicrob Agents Chemother. 2021 Apr; 65(4): e01436-20. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8097474/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	66.47

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 752.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Stracquadanio S, Torti E, Longshaw C, Henriksen AS, Stefani S. In vitro activity of cefiderocol and comparators against isolates of Gram-negative pathogens from a range of infection sources: SIDERO-WT-2014-2018 studies in Italy. J Glob Antimicrob Resist. 2021 May 18;25:390-398. doi: 10.1016/j.jgar.2021.04.019. Epub ahead of print. PMID: 34020073. 2. Pybus CA, Felder-Scott C, Obuekwe V, Greenberg DE. Cefiderocol Retains Antibiofilm Activity in Multidrug-Resistant Gram-Negative Pathogens. Antimicrob Agents Chemother. 2021 Jan 20;65(2):e01194-20. doi: 10.1128/AAC.01194-20. PMID: 33199383; PMCID: PMC7849010. 3. Nakamura R, Oota M, Matsumoto S, Sato T, Yamano Y. In Vitro Activity and In Vivo Efficacy of Cefiderocol against Stenotrophomonas maltophilia. Antimicrob Agents Chemother. 2021 Mar 18;65(4):e01436-20. doi: 10.1128/AAC.01436-20. PMID: 33526491; PMCID: PMC8097474. 4. Sato T, Yamawaki K. Cefiderocol: Discovery, Chemistry, and In Vivo Profiles of a Novel Siderophore Cephalosporin. Clin Infect Dis. 2019 Nov 13;69(Suppl 7):S538-S543. doi: 10.1093/cid/ciz826. PMID: 31724047; PMCID: PMC6853759.

In vitro protocol:

In vivo protocol:

1. Nakamura R, Oota M, Matsumoto S, Sato T, Yamano Y. In Vitro Activity and In Vivo Efficacy of Cefiderocol against Stenotrophomonas maltophilia. Antimicrob Agents Chemother. 2021 Mar 18;65(4):e01436-20. doi: 10.1128/AAC.01436-20. PMID: 33526491; PMCID: PMC8097474. 2. Sato T, Yamawaki K. Cefiderocol: Discovery, Chemistry, and In Vivo Profiles of a Novel Siderophore Cephalosporin. Clin Infect Dis. 2019 Nov 13;69(Suppl 7):S538-S543. doi: 10.1093/cid/ciz826. PMID: 31724047; PMCID: PMC6853759.

1: Yamano Y. In Vitro Activity of Cefiderocol Against a Broad Range of Clinically Important Gram-negative Bacteria. Clin Infect Dis. 2019 Nov 13;69(Supplement_7):S544-S551. doi: 10.1093/cid/ciz827. PubMed PMID: 31724049; PubMed Central PMCID: PMC6853761. 2: Echols R, Ariyasu M, Nagata TD. Pathogen-focused Clinical Development to Address Unmet Medical Need: Cefiderocol Targeting Carbapenem Resistance. Clin Infect Dis. 2019 Nov 13;69(Supplement_7):S559-S564. doi: 10.1093/cid/ciz829. PubMed PMID: 31724048; PubMed Central PMCID: PMC6853756. 3: Sato T, Yamawaki K. Cefiderocol: Discovery, Chemistry, and In Vivo Profiles of a Novel Siderophore Cephalosporin. Clin Infect Dis. 2019 Nov 13;69(Supplement_7):S538-S543. doi: 10.1093/cid/ciz826. PubMed PMID: 31724047; PubMed Central PMCID: PMC6853759. 4: Bonomo RA. Cefiderocol: A Novel Siderophore Cephalosporin Defeating Carbapenem-resistant Pathogens. Clin Infect Dis. 2019 Nov 13;69(Supplement_7):S519-S520. doi: 10.1093/cid/ciz823. PubMed PMID: 31724046; PubMed Central PMCID: PMC6853757. 5: Katsube T, Echols R, Wajima T. Pharmacokinetic and Pharmacodynamic Profiles of Cefiderocol, a Novel Siderophore Cephalosporin. Clin Infect Dis. 2019 Nov 13;69(Supplement_7):S552-S558. doi: 10.1093/cid/ciz828. PubMed PMID: 31724042; PubMed Central PMCID: PMC6853762. 6: Kidd JM, Abdelraouf K, Nicolau DP. Efficacy of Humanized Cefiderocol Exposure is Unaltered by Host Iron Overload in the Thigh Infection Model. Antimicrob Agents Chemother. 2019 Oct 28. pii: AAC.01767-19. doi: 10.1128/AAC.01767-19. [Epub ahead of print] PubMed PMID: 31658966. 7: Chen IH, Kidd JM, Abdelraouf K, Nicolau DP. Comparative In Vivo Antibacterial Activity of Human-Simulated Exposures of Cefiderocol and Ceftazidime against Stenotrophomonas maltophilia in the Murine Thigh Model. Antimicrob Agents Chemother. 2019 Oct 7. pii: AAC.01558-19. doi: 10.1128/AAC.01558-19. [Epub ahead of print] PubMed PMID: 31591126. 8: Stevens RW, Clancy M. Compassionate Use of Cefiderocol in the Treatment of an Intraabdominal Infection Due to Multidrug-Resistant Pseudomonas aeruginosa: A Case Report. Pharmacotherapy. 2019 Nov;39(11):1113-1118. doi: 10.1002/phar.2334. Epub 2019 Oct 22. PubMed PMID: 31550054. 9: Sanabria C, Migoya E, Mason JW, Stanworth SH, Katsube T, Machida M, Narukawa Y, Den Nagata T. Effect of Cefiderocol, a Siderophore Cephalosporin, on QT/QTc Interval in Healthy Adult Subjects. Clin Ther. 2019 Sep;41(9):1724-1736.e4. doi: 10.1016/j.clinthera.2019.07.006. Epub 2019 Aug 1. PubMed PMID: 31378318. 10: Trecarichi EM, Quirino A, Scaglione V, Longhini F, Garofalo E, Bruni A, Biamonte E, Lionello R, Serapide F, Mazzitelli M, Marascio N, Matera G, Liberto MC, Navalesi P, Torti C; IMAGES Group . Successful treatment with cefiderocol for compassionate use in a critically ill patient with XDR Acinetobacter baumannii and KPC-producing Klebsiella pneumoniae: a case report. J Antimicrob Chemother. 2019 Nov 1;74(11):3399-3401. doi: 10.1093/jac/dkz318. PubMed PMID: 31369095. 11: Nakamura R, Ito-Horiyama T, Takemura M, Toba S, Matsumoto S, Ikehara T, Tsuji M, Sato T, Yamano Y. In Vivo Pharmacodynamic Study of Cefiderocol, a Novel Parenteral Siderophore Cephalosporin, in Murine Thigh and Lung Infection Models. Antimicrob Agents Chemother. 2019 Aug 23;63(9). pii: e02031-18. doi: 10.1128/AAC.02031-18. Print 2019 Sep. PubMed PMID: 31262762; PubMed Central PMCID: PMC6709502. 12: Katsube T, Saisho Y, Shimada J, Furuie H. Intrapulmonary pharmacokinetics of cefiderocol, a novel siderophore cephalosporin, in healthy adult subjects. J Antimicrob Chemother. 2019 Jul 1;74(7):1971-1974. doi: 10.1093/jac/dkz123. PubMed PMID: 31220260; PubMed Central PMCID: PMC6587409. 13: Jean SS, Hsueh SC, Lee WS, Hsueh PR. Cefiderocol: a promising antibiotic against multidrug-resistant Gram-negative bacteria. Expert Rev Anti Infect Ther. 2019 May;17(5):307-309. doi: 10.1080/14787210.2019.1612240. Epub 2019 May 6. PubMed PMID: 31055983. 14: Hackel MA, Tsuji M, Yamano Y, Echols R, Karlowsky JA, Sahm DF. Reproducibility of broth microdilution MICs for the novel siderophore cephalosporin, cefiderocol, determined using iron-depleted cation-adjusted Mueller-Hinton broth. Diagn Microbiol Infect Dis. 2019 Aug;94(4):321-325. doi: 10.1016/j.diagmicrobio.2019.03.003. Epub 2019 Mar 23. PubMed PMID: 31029489. 15: Miyazaki S, Katsube T, Shen H, Tomek C, Narukawa Y. Metabolism, Excretion, and Pharmacokinetics of [(14) C]-Cefiderocol (S-649266), a Siderophore Cephalosporin, in Healthy Subjects Following Intravenous Administration. J Clin Pharmacol. 2019 Jul;59(7):958-967. doi: 10.1002/jcph.1386. Epub 2019 Feb 7. PubMed PMID: 30730562; PubMed Central PMCID: PMC6593826. 16: Zhanel GG, Golden AR, Zelenitsky S, Wiebe K, Lawrence CK, Adam HJ, Idowu T, Domalaon R, Schweizer F, Zhanel MA, Lagacé-Wiens PRS, Walkty AJ, Noreddin A, Lynch Iii JP, Karlowsky JA. Cefiderocol: A Siderophore Cephalosporin with Activity Against Carbapenem-Resistant and Multidrug-Resistant Gram-Negative Bacilli. Drugs. 2019 Feb;79(3):271-289. doi: 10.1007/s40265-019-1055-2. Review. PubMed PMID: 30712199. 17: Huttner A. Cefiderocol for treatment of complicated urinary tract infections - Author's reply. Lancet Infect Dis. 2019 Jan;19(1):24-25. doi: 10.1016/S1473-3099(18)30728-X. PubMed PMID: 30587291. 18: Portsmouth S, Echols R, Den Nagata T. Cefiderocol for treatment of complicated urinary tract infections. Lancet Infect Dis. 2019 Jan;19(1):23-24. doi: 10.1016/S1473-3099(18)30721-7. PubMed PMID: 30587290. 19: Wagenlehner FME, Naber KG. Cefiderocol for treatment of complicated urinary tract infections. Lancet Infect Dis. 2019 Jan;19(1):22-23. doi: 10.1016/S1473-3099(18)30722-9. PubMed PMID: 30587289. 20: Portsmouth S, van Veenhuyzen D, Echols R, Machida M, Ferreira JCA, Ariyasu M, Tenke P, Nagata TD. 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. 2018 Dec;18(12):1319-1328. doi: 10.1016/S1473-3099(18)30554-1. Epub 2018 Oct 25. PubMed PMID: 30509675.

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