Compound ID | 2035

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Pipemidic acid

Class: Quinolone

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: DNA synthesis inhibitor. Binds to type II topoisomerases, gyrase and topoisomerase IV to inhibitor DNA cleavage and ligation reactions; bacterial topoisomerase inhibitor
Description: Synthetic pyridopyrimidine compound, derivative of piromidic acid. Similar to nalidixic acid. Also used as K+ channel blocker.
Year first mentioned: 1974
Highest development stage: Approved
Development status: Withdrawn
Reason dropped: Safety concerns
Chemical structure(s):
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Molecular weight: 303.32
Iso. SMILES: CCN1C=C(C(=O)C2=CN=C(N=C21)N3CCNCC3)C(=O)O
InChI Key: JOHZPMXAZQZXHR-UHFFFAOYSA-N
Can. SMILES: CCN1C=C(C(=O)C2=C1N=C(N=C2)N3CCNCC3)C(=O)O
InChI: InChI=1S/C14H17N5O3/c1-2-18-8-10(13(21)22)11(20)9-7-16-14(17-12(9)18)19-5-3-15-4-6-19/h7-8,15H,2-6H2,1H3,(H,21,22)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/4831
Guide to Pharmacology: pipemidic acid
Citations:
  • https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC352440&blobtype=pdf
  • https://journals.asm.org/doi/10.1128/AAC.8.2.132
  • https://link.springer.com/chapter/10.1007/978-1-4684-3126-1_61

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