Pivmecillinam (Prodrug of Amdinocillin)

Synonym(s): Pivya  |  Amdinocillin pivoxil

Class: Beta-lactam (penicillin)

Spectrum of activity:	Gram-negative
Details of activity:	Used primarily in the treatment of lower UTI's. Also uses the trade names: Selexid, Penomax and Coactabs; binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Enterobacteriaceae incl. ESBL producers
Description:	Prodrug of mecillinam. Used for oral therapy of urinary tract infections.
Institute where first reported:	Leo Pharmaceutical Products; Utility Therapeutics
Year first mentioned:	1975
Highest developmental phase:	Approved by FDA in 2024
Development status:	Approved

Chemical structure(s):
Canonical SMILES:	CC(C)(C)C(=O)OCOC(=O)[C@H]1C(C)(C)S[C@@H]2[C@@H](C(=O)N12)N=CN3CCCCCC3
Isomeric SMILES:	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C
InChI:	InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
InChI Key:	NPGNOVNWUSPMDP-HLLBOEOZSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/115163

External links:
Guide to Pharmacology:	pivmecillinam
Main Source:	https://academic.oup.com/jac/article/73/9/2503/5046991?searchresult=1
Citations:	https://academic.oup.com/jac/article/46/suppl_1/35/2473592 https://pubmed.ncbi.nlm.nih.gov/1157572/ https://pubmed.ncbi.nlm.nih.gov/30518669/ https://pmc.ncbi.nlm.nih.gov/articles/PMC9118732/