Pipemidic acid

Class: Quinolone

Spectrum of activity:	Gram-negative
Details of activity:	Binds to type II topoisomerases, gyrase and topoisomerase IV and thus, inhibits DNA cleavage and ligation reactions. It kills bacterial cells by increasing the concentration of enzyme–DNA cleavage complexes, thereby inhibiting cell replication.
Description:	Synthetic pyridopyrimidine compound, derivative of piromidic acid. Similar to nalidixic acid. Also used as K+ channel blocker.
Year first mentioned:	1974
Development status:	Approved, off-patent, discontinued in most countries

Chemical structure(s):
Canonical SMILES:	CCN1C=C(C(=O)C2=C1N=C(N=C2)N3CCNCC3)C(=O)O
Isomeric SMILES:	CCN1C=C(C(=O)C2=CN=C(N=C21)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)
InChI Key:	JOHZPMXAZQZXHR-UHFFFAOYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/4831

External links:
Guide to Pharmacology:	pipemidic acid
Main Source:	https://link.springer.com/chapter/10.1007/978-1-4684-3126-1_61
Citations:	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC352440&blobtype=pdf https://journals.asm.org/doi/10.1128/AAC.8.2.132