Bacampicillin

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), ampicillin-ester. Oral application
Institute where first reported:	Pfizer
Year first mentioned:	1975
Highest developmental phase:	Approved by FDA in 1980
Development status:	Discontinued

Chemical structure(s):
Canonical SMILES:	CCOC(=O)OC(C)OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@@H](C(=O)N12)NC(=O)[C@@H](C3=CC=CC=C3)N
Isomeric SMILES:	CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](C3=CC=CC=C3)N)(C)C
InChI:	InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChI Key:	PFOLLRNADZZWEX-FFGRCDKISA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/441397

External links:
Guide to Pharmacology:	bacampicillin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/1211909/
Citation:	https://pubmed.ncbi.nlm.nih.gov/6762528/