Compound ID | 1896
Class: Beta-lactam (cephalosporin, second 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 against many Enterobacteriaceae but vulnerable to extended-spectum beta-lactamases (ESBL) |
Description: | Semisynthetic Cephalosporin, derived from Cephalosporin C. Oral application |
Year first mentioned: | 1983 |
Development status: | Approved, off-patent, discontinued in most countries |
Chemical structure(s): | |
Canonical SMILES: | C/C=C/C1=C(C(=O)O)N2C(=O)[C@H]([C@H]2SC1)NC(=O)[C@@H](C3=CC=C(C=C3)O)N |
Isomeric SMILES: | C/C=C/C1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O |
InChI: | InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1 |
InChI Key: | WDLWHQDACQUCJR-ZAMMOSSLSA-N |
Structure link: | https://pubchem.ncbi.nlm.nih.gov/compound/5281006 |
External links: | |
Guide to Pharmacology: | cefprozil |
Main Source: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4675762/ |