Cefpirome

Class: Beta-lactam (cephalosporin, fourth generation)

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-negative bacteria but vulnerable to higher levels of extended-spectum beta-lactamases (ESBL) and high resistance rates in Pseudomonas aeruginosa
Description:	Semisynthetic Cephalosporine, derived from Cephalosporin C
Year first mentioned:	1983
Development status:	Approved, off-patent, discontinued in many countries

Chemical structure(s):
Canonical SMILES:	CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@@H]2C(=O)N3C(=C(C[N+]4=C5CCCC5=CC=C4)CS[C@H]23)C(=O)[O-]
Isomeric SMILES:	CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]
InChI:	InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1
InChI Key:	DKOQGJHPHLTOJR-WHRDSVKCSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5479539

External links:
Guide to Pharmacology:	cefpirome
Main Source:	https://pubmed.ncbi.nlm.nih.gov/8261711/
Citations:	https://pubmed.ncbi.nlm.nih.gov/1601761/ https://pubmed.ncbi.nlm.nih.gov/9211085/