Metampicillin

Synonym(s): Methylenampicillin

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:	Prodrug of ampicillin
Year first mentioned:	1969
Highest developmental phase:	Approved
Development status:	Approved, off-patent, not 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=CC=CC=C3)N=C
Isomeric SMILES:	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N=C)C(=O)O)C
InChI:	InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)/t10-,11-,12+,15-/m1/s1
InChI Key:	FZECHKJQHUVANE-MCYUEQNJSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/6713928

External links:
Guide to Pharmacology:	metampicillin
Main Source:	https://doi.org/10.1159/000220849
Citations:	https://www.nature.com/articles/s41598-020-74990-1 https://doi.org/10.1159/000220849