Compound ID | 1882
Class: Beta-lactam (cephalosporin, first 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-positive bacteria and moderately against Enterobacteriaceae but high resistance rates in Enterobacteriaceae |
Description: | Semisynthetic Cephalosporin, derived from Cephalosporin C. Oral application |
Year first mentioned: | 1971 |
Highest developmental phase: | Approved by FDA in 1974 |
Development status: | Discontinued |
Chemical structure(s): | |
Canonical SMILES: | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@H]([C@H]2SC1)NC(=O)CSC3=CC=NC=C3 |
Isomeric SMILES: | CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O |
InChI: | InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1 |
InChI Key: | UQLLWWBDSUHNEB-CZUORRHYSA-N |
Structure link: | https://pubchem.ncbi.nlm.nih.gov/compound/30699 |
External links: | |
Guide to Pharmacology: | cefapirin |
Main Source: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC376442/ |