Compound ID | 1340

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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):
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Molecular weight: 439.57
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C
InChI Key: NPGNOVNWUSPMDP-HLLBOEOZSA-N
Can. SMILES: CC(C)(C)C(=O)OCOC(=O)[C@H]1C(C)(C)S[C@@H]2[C@@H](C(=O)N12)N=CN3CCCCCC3
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/115163
Guide to Pharmacology: pivmecillinam
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/
  • https://academic.oup.com/jac/article/73/9/2503/5046991?searchresult=1

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