Cefpirome - Misplaced Pages

Chemical compound Pharmaceutical compound

Cefpirome
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01DE02 (WHO)
Identifiers
IUPAC name 1-{-2-carboxylato-8-oxo-5-thia-1-azabicyclooct-2-en-3-yl]methyl}-5H,6H,7H-cyclopentapyridin-1-ium
CAS Number	84957-29-9
PubChem CID	6917674
ChemSpider	23089536
UNII	S72Q2F09HY
KEGG	D07649
ChEMBL	ChEMBL2106076
CompTox Dashboard (EPA)	DTXSID2048244
Chemical and physical data
Formula	C₂₂H₂₂N₆O₅S₂
Molar mass	514.58 g·mol
3D model (JSmol)	Interactive image
SMILES CON=C(c1csc(n1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C4cccc5c4CCC5)C(=O)
InChI InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20+/m1/s1 Key:DKOQGJHPHLTOJR-XECLGWKCSA-N
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Cefpirome is a fourth-generation cephalosporin. Trade names include Cefrom, Keiten, Broact, and Cefir. Cefpirome is considered highly active against Gram-negative bacteria, including Pseudomonas aeruginosa, and Gram-positive bacteria.

Spectrum of bacterial susceptibility and resistance

Bacteroides fragilis, enterococci, Pseudomonas spp. and staphylococci are resistant to cefpirome sulfate, and some Haemophilus spp. and pneumococci have developed resistance to it to varying degrees.

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

Aminopenicillins (3rd generation)	Amoxicillin Ampicillin (Pivampicillin Hetacillin Bacampicillin Lenampicillin Metampicillin Talampicillin) Epicillin
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin / Carindacillin Temocillin
Ureidopenicillins (4th generation)	Piperacillin Azlocillin Mezlocillin
Other	Mecillinam (Pivmecillinam) Sulbenicillin

1st generation	Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefonicid Ceforanide Cefuzonam Cephamycin (Cefoxitin Cefotetan Cefminox Cefbuperazone Cefmetazole) Carbacephem (Loracarbef)
3rd generation	Cefixime Ceftriaxone Cefotaxime Antipseudomonal (Ceftazidime Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem (Flomoxef Latamoxef)
4th generation	Cefepime Cefozopran Cefpirome Cefquinome
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol
Veterinary	Ceftiofur Cefquinome Cefovecin

Combinations

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

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