Compound ID | 1937

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Piperacillin

Class: Beta-lactam (ureidopenicillin)

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-negative bacteria including Pseudomonas aeruginosa, but vulnerable to beta-lactamases
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA). Closely related to azlocillin. Available in fixed combination with tazobactam. Parenteral application
Year first mentioned: 1974
Highest developmental phase: Approved by FDA in 1981
Development status: Approved
Chemical structure(s):
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Molecular weight: 517.56
Iso. SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI Key: IVBHGBMCVLDMKU-GXNBUGAJSA-N
Can. SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@@H]3C(=O)N4[C@@H](C(=O)O)C(C)(C)S[C@H]34
InChI: InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/43672
Guide to Pharmacology: piperacillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/29385448/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC352246/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8866359/
  • https://www.sciencedirect.com/sdfe/pdf/download/eid/1-s2.0-S0025712516300323/first-page-pdf

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