Cefazedone - Misplaced Pages

Chemical compound Pharmaceutical compound

Cefazedone
Clinical data

ATC code	J01DB06 (WHO)
Identifiers
IUPAC name (6R,7R)-7-{amino}-3--8-oxo-5-thia-1-azabicyclo oct-2-ene-2-carboxylic acid
CAS Number	56187-47-4
PubChem CID	71736
ChemSpider	64780
UNII	7Y86X0D799
KEGG	D07237
ChEBI	CHEBI:131731
ChEMBL	ChEMBL2107636
CompTox Dashboard (EPA)	DTXSID50204733
ECHA InfoCard	100.121.805
Chemical and physical data
Formula	C₁₈H₁₅Cl₂N₅O₅S₃
Molar mass	548.43 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS12NC(=O)CN/3/C=C(/Cl)C(=O)C(\Cl)=C\3)CSc4nnc(s4)C)C(=O)O
InChI InChI=1S/C18H15Cl2N5O5S3/c1-7-22-23-18(33-7)32-6-8-5-31-16-12(15(28)25(16)13(8)17(29)30)21-11(26)4-24-2-9(19)14(27)10(20)3-24/h2-3,12,16H,4-6H2,1H3,(H,21,26)(H,29,30)/t12-,16-/m1/s1 Key:VTLCNEGVSVJLDN-MLGOLLRUSA-N
(verify)

Cefazedone is a cephalosporin antibiotic.

References

Wahlig H, Dingeldein E, Mitsuhashi S, Kawabe H (1979). "Cefazedone: microbiological evaluation in comparison with cephalothin and cefazolin". Arzneimittel-Forschung. 29 (2a): 369–78. PMID 582712.

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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