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 ;
	(what is this?) (verify)

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^[when?] 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,^{[not verified in body]} the only other fifth-generation cephalosporin to date,^[when?] 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).^{[not verified in body]}

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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Ceftaroline fosamil

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