Penamecillin

Class: Beta-lactam (penicillin)

Spectrum of activity:	Gram-positive
Details of activity:	Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria, but vulnerable to penicillinases produced by staphylococci
Description:	Prodrug of benzylpenicillin
Year first mentioned:	1966
Development status:	Approved, off-patent, not available in most countries

Chemical structure(s):
Canonical SMILES:	CC(=O)OCOC(=O)[C@H]1C(C)(C)S[C@@H]2[C@@H](C(=O)N12)NC(=O)CC3=CC=CC=C3
Isomeric SMILES:	CC(=O)OCOC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)(C)C
InChI:	InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1
InChI Key:	NLOOMWLTUVBWAW-HLLBOEOZSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/10250769

External links:
Guide to Pharmacology:	penamecillin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1510697/