Cefteram

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Cefteram
Cefteram.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (6R,7R)-7-([(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino)-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H17N9O5S2
Molar mass 479.49 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3nc(sc3)N)Cn4nc(nn4)C)C(=O)O

Cefteram (INN) is a third-generation cephalosporin antibiotic. [1]

Synthesis

Cefteram synthesis.svg

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. [2] [3]

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References

  1. Yamaguchi K, Ohno A, Takahashi S, Hayashi M, Yamanaka K, Hirakata Y, Mitsuyama J (January 1998). "[In vitro antibacterial activities of cefteram and other beta-lactam agents against recent clinical isolates]". The Japanese Journal of Antibiotics. 51 (1): 11–25. PMID   9557273.
  2. "Cefteram". chemdrug.com. Retrieved 2024-07-03.
  3. USpatent 4489072,Hiroshi Sadaki, et al.,issued 1984-12-18, assigned to Toyama Chemical Co Ltd