Epicillin

Class: Beta-lactam (aminopenicillin)

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 some Enterobacteriaceae, but vulnerable to penicillinases produced by staphylococci and E. coli
Description:	Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA). Closely related to ampicilllin. Parenteral and oral application
Year first mentioned:	1971
Development status:	Approved, off-patent, not approved or available in most countries

Chemical structure(s):
Canonical SMILES:	CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)[C@@H](C3=CCC=CC3)N
Isomeric SMILES:	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CCC=CC3)N)C(=O)O)C
InChI:	InChI=1S/C16H21N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-4,7,9-11,14H,5-6,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChI Key:	RPBAFSBGYDKNRG-NJBDSQKTSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/71392

External links:
Guide to Pharmacology:	epicillin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/4265722/
Citations:	https://pubmed.ncbi.nlm.nih.gov/7191790/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC416262/