Cefteram - Misplaced Pages

Chemical compound Pharmaceutical compound

Cefteram
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01DD18 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (6R,7R)-7-(amino)-3--8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number	82547-58-8
PubChem CID	6537431
ChemSpider	4576594
UNII	74CQ4Q3N63
KEGG	D07655
ChEMBL	ChEMBL2105953
CompTox Dashboard (EPA)	DTXSID7048821
Chemical and physical data
Formula	C₁₆H₁₇N₉O₅S₂
Molar mass	479.49 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS12NC(=O)C(=N\OC)\c3nc(sc3)N)Cn4nc(nn4)C)C(=O)O

Cefteram (INN) is a third-generation cephalosporin antibiotic.

Synthesis

The reaction of 7-aminocephalosporanic acid (1) with the methyl-substituted tetrazole (2) gives the intermediate (3). Protection with diazodiphenylmethane (4) produces (5). Amide formation with the thiazole carboxylic acid (6) gives (7), which is deprotected with trifluoroacetic acid to yield cefteram.

Yamaguchi K, Ohno A, Takahashi S, Hayashi M, Yamanaka K, Hirakata Y, Mitsuyama J (January 1998). "". The Japanese Journal of Antibiotics. 51 (1): 11–25. PMID 9557273.
"Cefteram". chemdrug.com. Retrieved 2024-07-03.
US patent 4489072, Hiroshi Sadaki, et al., issued 1984-12-18, assigned to Toyama Chemical Co Ltd

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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