Ceftaroline fosamil

Ceftaroline fosamil
Clinical data
Trade names	Teflaro, Zinforo
Other names	PPI 0903, TAK-599
AHFS/Drugs.com	Monograph
MedlinePlus	a611014
License data	EU EMA: by INN; US DailyMed: Ceftaroline_fosamil; US FDA: Ceftaroline;
Pregnancy; category	AU: B1;
Routes of; administration	Intravenous
ATC code	J01DI02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	20%
Elimination half-life	2.5 hours
Excretion	Urine (88%), faeces (6%)
Identifiers
	IUPAC name (6R,7R)-7-[(2Z)-2-ethoxyimino-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;
CAS Number	229016-73-3 ; anhydrous: 400827-46-5 ;
PubChem CID	16007393; anhydrous: 9852981;
DrugBank	DB06590 ;
ChemSpider	8028692 ;
UNII	7P6FQA5D21; anhydrous: EZ9W6O5S09 ;
KEGG	D08884;
ChEBI	CHEBI:70718 ;
ChEMBL	ChEMBL501122 ;
CompTox Dashboard (EPA)	DTXSID60177444 ;
Chemical and physical data
Formula	C22H21N8O8PS4
Molar mass	684.67 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4N3/C(=C(/Sc2nc(c1cc[n+](cc1)C)cs2)CS[C@@H]3[C@@H]4NC(=O)C(=N\OCC)/c5nc(sn5)NP(=O)(O)O)C([O-])=O;
	InChI InChI=1S/C22H21N8O8PS4/c1-3-38-26-13(16-25-21(43-28-16)27-39(35,36)37)17(31)24-14-18(32)30-15(20(33)34)12(9-40-19(14)30)42-22-23-11(8-41-22)10-4-6-29(2)7-5-10/h4-8,14,19H,3,9H2,1-2H3,(H4-,24,25,27,28,31,33,34,35,36,37)/b26-13-/t14-,19-/m1/s1 ; Key:ZCCUWMICIWSJIX-NQJJCJBVSA-N ;
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Ceftaroline fosamil (INN) /sɛfˈtæroʊliːn/, brand name Teflaro in the US and Zinforo in Europe,^[1]^[2] is a cephalosporin antibiotic with anti-MRSA activity.^[3] Ceftaroline fosamil is a prodrug of ceftaroline. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and other Gram-positive bacteria. It retains some activity of later-generation cephalosporins having broad-spectrum activity against Gram-negative bacteria, but its effectiveness is relatively much weaker.^[4]^[5] It is currently being investigated for community-acquired pneumonia^[6] and complicated skin and skin structure infection.^[7]^[8]^[9]

Ceftaroline is being developed by Forest Laboratories, under a license from Takeda.^[9] Ceftaroline received approval from the U.S. Food and Drug Administration (FDA) for the treatment of community-acquired bacterial pneumonia and acute bacterial skin infections on 29 October 2010.^[10] In vitro studies show it has a similar spectrum to ceftobiprole, the only other fifth-generation cephalosporin to date, although no head-to-head clinical trials have been conducted. Ceftaroline and ceftobiprole are on an unnamed subclass of cephalosporins by the Clinical and Laboratory Standards Institute (CLSI).

It was removed from the World Health Organization's List of Essential Medicines in 2019.^[11]

^ ^a ^b "Teflaro- ceftaroline fosamil powder, for solution". DailyMed. 24 September 2019. Retrieved 1 March 2020.
^ ^a ^b "Zinforo EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 1 March 2020.
^ Duplessis C, Crum-Cianflone NF (February 2011). "Ceftaroline: A New Cephalosporin with Activity against Methicillin-Resistant Staphylococcus aureus (MRSA)". Clinical Medicine Reviews in Therapeutics. 3: a2466. doi:10.4137/CMRT.S1637. PMC 3140339. PMID 21785568.
^ Karlowsky JA, Adam HJ, Decorby MR, Lagacé-Wiens PR, Hoban DJ, Zhanel GG (June 2011). "In vitro activity of ceftaroline against gram-positive and gram-negative pathogens isolated from patients in Canadian hospitals in 2009". Antimicrobial Agents and Chemotherapy. 55 (6): 2837–2846. doi:10.1128/aac.01787-10. PMC 3101400. PMID 21402844.
^ Flamm RK, Sader HS, Jones RN (October 2010). "Spectrum and potency of ceftaroline against leading pathogens causing community-acquired respiratory tract and skin and soft tissue infections in Latin America, 2010". The Brazilian Journal of Infectious Diseases. 17 (5): 564–572. doi:10.1016/j.bjid.2013.02.008. PMC 9425132. PMID 23916453.
^ Cite error: The named reference eckberg2009 was invoked but never defined (see the help page).
^ Cite error: The named reference corey2008 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid19207097 was invoked but never defined (see the help page).
^ ^a ^b Parish D, Scheinfeld N (February 2008). "Ceftaroline fosamil, a cephalosporin derivative for the potential treatment of MRSA infection". Current Opinion in Investigational Drugs. 9 (2): 201–209. PMID 18246523.
^ "Forest Announces FDA Approval of Teflaro (ceftaroline fosamil) for the Treatment of Community-Acquired Bacterial Pneumonia and Acute Bacterial Skin and Skin Structure Infection" (Press release). Forest Laboratories. 29 October 2010. Retrieved 30 October 2010.
^ World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.

[Teflaro_FDA_label-1] "Teflaro- ceftaroline fosamil powder, for solution". DailyMed. 24 September 2019. Retrieved 1 March 2020.

[Zinforo_EPAR-2] "Zinforo EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 1 March 2020.

[pmid20001879-3] Duplessis C, Crum-Cianflone NF (February 2011). "Ceftaroline: A New Cephalosporin with Activity against Methicillin-Resistant Staphylococcus aureus (MRSA)". Clinical Medicine Reviews in Therapeutics. 3: a2466. doi:10.4137/CMRT.S1637. PMC 3140339. PMID 21785568.

[4] Karlowsky JA, Adam HJ, Decorby MR, Lagacé-Wiens PR, Hoban DJ, Zhanel GG (June 2011). "In vitro activity of ceftaroline against gram-positive and gram-negative pathogens isolated from patients in Canadian hospitals in 2009". Antimicrobial Agents and Chemotherapy. 55 (6): 2837–2846. doi:10.1128/aac.01787-10. PMC 3101400. PMID 21402844.

[5] Flamm RK, Sader HS, Jones RN (October 2010). "Spectrum and potency of ceftaroline against leading pathogens causing community-acquired respiratory tract and skin and soft tissue infections in Latin America, 2010". The Brazilian Journal of Infectious Diseases. 17 (5): 564–572. doi:10.1016/j.bjid.2013.02.008. PMC 9425132. PMID 23916453.

[eckberg2009-6] Cite error: The named reference eckberg2009 was invoked but never defined (see the help page).

[corey2008-7] Cite error: The named reference corey2008 was invoked but never defined (see the help page).

[pmid19207097-8] Cite error: The named reference pmid19207097 was invoked but never defined (see the help page).

[pmid18246523-9] Parish D, Scheinfeld N (February 2008). "Ceftaroline fosamil, a cephalosporin derivative for the potential treatment of MRSA infection". Current Opinion in Investigational Drugs. 9 (2): 201–209. PMID 18246523.

[10] "Forest Announces FDA Approval of Teflaro (ceftaroline fosamil) for the Treatment of Community-Acquired Bacterial Pneumonia and Acute Bacterial Skin and Skin Structure Infection" (Press release). Forest Laboratories. 29 October 2010. Retrieved 30 October 2010.

[11] World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.

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