Ceftetrame (Ro15-8074)

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

Class: Beta-lactam (cephalosporin, third generation)

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	This compound demonstrated no activity against staphylococci but ten times more active than cefaclor and cefalexin against Streptococcus pyogenes (1); inhibits cell wall synthesis; binds to penicillin-binding proteins (PBP); active against Gram-positive bacteria and against many Enterobacteriaceae but vulnerable to extended-spectum beta-lactamases (ESBL)
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)
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):
Canonical 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
Isomeric 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:	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
InChI Key:	XSPUSVIQHBDITA-RKYNPMAHSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/6537431

External links:
Guide to Pharmacology:	cefteram
Main Source:	https://pubmed.ncbi.nlm.nih.gov/25618776/
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