Compound ID | 2101

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Ceftetrame (Ro15-8074)

Synonym(s): Ro 19-5247  |  T2525  |  tomiron  |  Cefteram  |  T-2588  |  cefteram pivoxil (prodrug)  |  cefetamet

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds to penicillin-binding proteins (PBP); inactivated by extended-spectum beta-lactamases (ESBL)
Target Pathogen: This compound demonstrated no activity against staphylococci but ten times more active than cefaclor and cefalexin against Streptococcus pyogenes; active against Gram-positive bacteria and against many Enterobacteriaceae
Description: Faoagali JL. The antibiotic susceptibilities of 1659 clinical isolates to RO 15-8074, RO 19-5247 and RO 23-6240. Aust-J-Hosp-Pharm 1989;19214-217; semisynthetic Cephalosporine (cephem), derived from Cephalosporin C. Oral application as prodrug (Cefteram pivoxil); a third generation cephalosporin
Institute where first reported: Toyama Chemical, Japan; Roche, Japan
Year first mentioned: 1984
Highest developmental phase: Preclinical
Development status: Approved in Japan, off-patent
Reason Dropped: In preclinical trials on mice, penetration through the blood brain barrier and placenta were low (2)
Chemical structure(s):
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Molecular weight: 479.5
Iso. SMILES: CC1=NN(N=N1)CC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
InChI Key: XSPUSVIQHBDITA-RKYNPMAHSA-N
Can. SMILES: CC1=NN(CC2=C(C(=O)O)N3C(=O)[C@H]([C@H]3SC2)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)N=N1
InChI: InChI=1S/C16H17N9O5S2/c1-6-20-23-24(21-6)3-7-4-31-14-10(13(27)25(14)11(7)15(28)29)19-12(26)9(22-30-2)8-5-32-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b22-9-/t10-,14-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6537431
Guide to Pharmacology: cefteram
Citations:
  • https://www.ncbi.nlm.nih.gov/pubmed/3761550
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC269173/
  • http://www.ncbi.nlm.nih.gov/pubmed/3596808
  • https://pubmed.ncbi.nlm.nih.gov/25618776/

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