Ceftobiprole medocaril: Difference between revisions

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Ceftobiprole medocaril
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intravenous
ATC code	J01DI01 (WHO) ;
Legal status
Legal status	Withdrawn from the Canadian market; still marketed in Russia;
Identifiers
	IUPAC name (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-ylidene)- 2-nitroso-1-oxoethyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)- 3-pyrrolidinyl]-3-pyrrolidinylidene]methyl]-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	209467-52-7 ; 252188-71-9 (medocaril);
PubChem CID	6918430;
ChemSpider	21106277 ;
UNII	5T97333YZK;
KEGG	D08885 ;
ChEMBL	ChEMBL520642 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C20H22N8O6S2
Molar mass	534.568 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C3N1/C(=C(\CS[C@@H]1[C@@H]3NC(=O)C(\N=O)=C2/NSC(\N)=N2)/C=C4\CCN(C4=O)[C@@H]5CCNC5)C(O)=O;
	InChI InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,26H,1-4,6-7H2,(H2,21,24)(H,23,29)(H,32,33)/b8-5+,14-11+/t10-,12-,18-/m1/s1 ; Key:LXLDMYXULSBRCX-KOGKARRDSA-N ;
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Latest revision as of 18:51, 18 August 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Ceftobiprole (Zeftera/Zevtera) is a fifth-generation^[2] cephalosporin antibiotic with activity against methicillin-resistant Staphylococcus aureus, penicillin-resistant Streptococcus pneumoniae, Pseudomonas aeruginosa, and enterococci.^[3]^[4]^[5] It was discovered by Basilea Pharmaceutica^[6] and was developed by Johnson & Johnson Pharmaceutical Research and Development.^[7] It has been shown to be statistically noninferior to the combination of vancomycin and ceftazidime for the treatment of skin and soft tissue infections.^[8]

It has been described as a fifth-generation cephalosporin,^[9]^[10] though acceptance for this terminology is not universal.

Pharmacology

Like other cephalosporins, ceftobiprole inhibits bacterial growth by blocking penicillin-binding protein, a key enzyme involved in cell wall synthesis. Ceftobiprole inhibits the 2a penicillin-binding protein (PBP) of methicillin-resistant Staphylococcus aureus and the 2x PBP of Streptococcus pneumoniae,^[4] as well as the classic PBP-2 of MSSA. Ceftobiprole is resistant to staphylococcal β-lactamase.^[6]

Mode of administration

Ceftobiprole is given intravenously; it cannot be given by mouth.

Regulatory approvals

Ceftobiprole has been approved for use in Canada, Switzerland, and the European Union.^[11] It is under review by regulatory authorities in the United States, Australia, Russia, and South Africa.^[12] In November 2008, the US FDA declined to approve ceftobiprole, citing data integrity concerns with two of the supporting studies,^[13] and prompting Basilea to sue Johnson & Johnson for breach of license agreement on February 2009.^[14]

Synonyms

RO0639141-000^[6]
BAL9141^[15]
Ceftobiprole medocaril

References

↑ WHO International Working Group for Drug Statistics Methodology (August 27, 2008). "ATC/DDD Classification (FINAL): New ATC 5th level codes". WHO Collaborating Centre for Drug Statistics Methodology. Retrieved 2008-09-05.
↑ Kollef MH (December 2009). "New antimicrobial agents for methicillin-resistant Staphylococcus aureus". Crit Care Resusc. 11 (4): 282–6. PMID 20001879.
↑ Yun HC, Ellis MW, Jorgensen JH (2007). "Activity of ceftobiprole against community-associated methicillin-resistant Staphylococcus aureus isolates recently recovered from US military trainees". Diagnostic Microbiology and Infectious Disease. 59 (4): 463–6. doi:10.1016/j.diagmicrobio.2007.06.023. PMID 17911001.
↑ ^4.0 ^4.1 Widmer A (2008). "Ceftobiprole: A new option for treatment of skin and soft-tissue infections due to methicillin-resistant Staphylococcus aureus". Clin Infect Dis. 46 (5): 656–8. doi:10.1086/526528. PMID 18225983.
↑ Noel GJ, Bush K, Bagchi P, Ianus J, Strauss RS (2008). "A randomized, double-blind trial comparing ceftobiprole medocaril with vancomycin plus ceftazidime plus ceftazidime for the treatment of patients with complicated skin and skin-structure infections". Clin Infect Dis. 46 (5): 647–55. doi:10.1086/526527. PMID 18225981.
↑ ^6.0 ^6.1 ^6.2 Hebeisen P, Heinze-Krauss I, Angehrn P; et al. (2001). "In vitro and in vivo properties of Ro63-9141, a novel broad-spectrum cephalosporin with activity against methicillin-resistant staphylococci". Antimicrob Agents Chemother. 45 (3): 825–36. doi:10.1128/AAC.45.3.825-836.2001. PMC 90381. PMID 11181368.
↑ Basilea.com
↑ Noel, Gary J.; Karen Bush; Partha Bagchi; Juliana Ianus; Richard S. Strauss (2008). "A Randomized, Double-Blind Trial Comparing Ceftobiprole Medocaril with Vancomycin plus Ceftazidime for the Treatment of Patients with Complicated Skin and Skin-Structure Infections". Clin Infect Dis. 46 (5): 647-655. doi:10.1086/526527. PMID 18225981. |access-date= requires |url= (help)
↑ Widmer AF (March 2008). "Ceftobiprole: a new option for treatment of skin and soft-tissue infections due to methicillin-resistant Staphylococcus aureus". Clin. Infect. Dis. 46 (5): 656–8. doi:10.1086/526528. PMID 18225983.
↑ Kosinski MA, Joseph WS (July 2007). "Update on the treatment of diabetic foot infections". Clin Podiatr Med Surg. 24 (3): 383–96, vii. doi:10.1016/j.cpm.2007.03.009. PMID 17613382.
↑ Basilea antibiotic to treat pneumonia wins European backing. Reuters, ZURICH | Wed Oct 23, 2013.
↑ Basilea superbug drug approved in Canada, Reuters News, June 30, 2008
↑ http://www.dancewithshadows.com/pillscribe/ceftobiprole-antibiotic-to-fight-tougher-bacterial-infections-fails-to-win-approval-in-us/
↑ "Basilea Pharmaceutica Ltd. announces that the U.S. Food and Drug Administration (FDA) issued to the sponsor, Johnson & Johnson Pharmaceutical Research and Development, L.L.C. (Johnson & Johnson PRD), a Complete Response Letter on ceftobiprole for the treatment of complicated skin and skin structure infections (cSSSI" (Press release). Basilea Pharmaceutica. 2009-07-02. Retrieved February 2, 2010.
↑ Jones RN, Deshpande LM, Mutnick AH, Biedenbach DJ (2002). "In vitro evaluation of BAL9141, a novel parenteral cephalosporin active against oxacillin-resistant staphylococci". J Antimicrob Chemother. 50 (6): 915–932. doi:10.1093/jac/dkf249. PMID 12461013.

[1] WHO International Working Group for Drug Statistics Methodology (August 27, 2008). "ATC/DDD Classification (FINAL): New ATC 5th level codes". WHO Collaborating Centre for Drug Statistics Methodology. Retrieved 2008-09-05.

[pmid20001879-2] Kollef MH (December 2009). "New antimicrobial agents for methicillin-resistant Staphylococcus aureus". Crit Care Resusc. 11 (4): 282–6. PMID 20001879.

[3] Yun HC, Ellis MW, Jorgensen JH (2007). "Activity of ceftobiprole against community-associated methicillin-resistant Staphylococcus aureus isolates recently recovered from US military trainees". Diagnostic Microbiology and Infectious Disease. 59 (4): 463–6. doi:10.1016/j.diagmicrobio.2007.06.023. PMID 17911001.

[2008Widmer-4] 4.0 ^4.1 Widmer A (2008). "Ceftobiprole: A new option for treatment of skin and soft-tissue infections due to methicillin-resistant Staphylococcus aureus". Clin Infect Dis. 46 (5): 656–8. doi:10.1086/526528. PMID 18225983.

[2008Noel-5] Noel GJ, Bush K, Bagchi P, Ianus J, Strauss RS (2008). "A randomized, double-blind trial comparing ceftobiprole medocaril with vancomycin plus ceftazidime plus ceftazidime for the treatment of patients with complicated skin and skin-structure infections". Clin Infect Dis. 46 (5): 647–55. doi:10.1086/526527. PMID 18225981.

[2001Hebeisen-6] 6.0 ^6.1 ^6.2 Hebeisen P, Heinze-Krauss I, Angehrn P; et al. (2001). "In vitro and in vivo properties of Ro63-9141, a novel broad-spectrum cephalosporin with activity against methicillin-resistant staphylococci". Antimicrob Agents Chemother. 45 (3): 825–36. doi:10.1128/AAC.45.3.825-836.2001. PMC 90381. PMID 11181368.

[7] Basilea.com

[8] Noel, Gary J.; Karen Bush; Partha Bagchi; Juliana Ianus; Richard S. Strauss (2008). "A Randomized, Double-Blind Trial Comparing Ceftobiprole Medocaril with Vancomycin plus Ceftazidime for the Treatment of Patients with Complicated Skin and Skin-Structure Infections". Clin Infect Dis. 46 (5): 647-655. doi:10.1086/526527. PMID 18225981. |access-date= requires |url= (help)

[pmid18225983-9] Widmer AF (March 2008). "Ceftobiprole: a new option for treatment of skin and soft-tissue infections due to methicillin-resistant Staphylococcus aureus". Clin. Infect. Dis. 46 (5): 656–8. doi:10.1086/526528. PMID 18225983.

[pmid17613382-10] Kosinski MA, Joseph WS (July 2007). "Update on the treatment of diabetic foot infections". Clin Podiatr Med Surg. 24 (3): 383–96, vii. doi:10.1016/j.cpm.2007.03.009. PMID 17613382.

[11] Basilea antibiotic to treat pneumonia wins European backing. Reuters, ZURICH | Wed Oct 23, 2013.

[12] Basilea superbug drug approved in Canada, Reuters News, June 30, 2008

[13] ttp://www.dancewithshadows.com/pillscribe/ceftobiprole-antibiotic-to-fight-tougher-bacterial-infections-fails-to-win-approval-in-us/

[14] "Basilea Pharmaceutica Ltd. announces that the U.S. Food and Drug Administration (FDA) issued to the sponsor, Johnson & Johnson Pharmaceutical Research and Development, L.L.C. (Johnson & Johnson PRD), a Complete Response Letter on ceftobiprole for the treatment of complicated skin and skin structure infections (cSSSI" (Press release). Basilea Pharmaceutica. 2009-07-02. Retrieved February 2, 2010.

[15] Jones RN, Deshpande LM, Mutnick AH, Biedenbach DJ (2002). "In vitro evaluation of BAL9141, a novel parenteral cephalosporin active against oxacillin-resistant staphylococci". J Antimicrob Chemother. 50 (6): 915–932. doi:10.1093/jac/dkf249. PMID 12461013.

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v t e Antibacterials: cell wall disruption (J01C-J01D)
Internal to membrane/ (inhibit peptidoglycan subunit synthesis and transport)	Template:Navbox subgroup
Glycopeptide/ (inhibit PG chain elongation)	Vancomycin # (Oritavancin, Telavancin) · Teicoplanin (Dalbavancin) · Ramoplanin
Beta-lactams/ (inhibit cross-links with PBP)	Template:Navbox subgroup
Other	Template:Navbox subgroup
# = WHO-EM

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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous
ATC code	J01DI01 (WHO) ^[1]
Legal status
Legal status	Withdrawn from the Canadian market; still marketed in Russia
Identifiers
IUPAC name (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-ylidene)- 2-nitroso-1-oxoethyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)- 3-pyrrolidinyl]-3-pyrrolidinylidene]methyl]-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	209467-52-7^N 252188-71-9 (medocaril)
PubChem CID	6918430
ChemSpider	21106277^Y
UNII	5T97333YZK
KEGG	D08885^Y
ChEMBL	ChEMBL520642^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₀H₂₂N₈O₆S₂
Molar mass	534.568 g/mol
3D model (JSmol)	Interactive image
SMILES O=C3N1/C(=C(\CS[C@@H]1[C@@H]3NC(=O)C(\N=O)=C2/NSC(\N)=N2)/C=C4\CCN(C4=O)[C@@H]5CCNC5)C(O)=O
InChI InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,26H,1-4,6-7H2,(H2,21,24)(H,23,29)(H,32,33)/b8-5+,14-11+/t10-,12-,18-/m1/s1^Y Key:LXLDMYXULSBRCX-KOGKARRDSA-N^Y
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