Pipemidic acid

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Pipemidic acid
Category Antibiotics
Catalog number BBF-03889
CAS 51940-44-4
Molecular Weight 303.32
Molecular Formula C14H17N5O3
Purity ≥95%

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Description

Pipemidic acid is a synthetic quinolone antibiotic agent as an ATP-sensitive K+ channel blocker.

Specification

Synonyms Deblaston; Pipram; Uromidin; RB 1489; RB-1489; RB1489
Shelf Life As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Storage Store at -20°C
IUPAC Name 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid
Canonical 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
Source Synthetic

Properties

Appearance White to Off-white Powder
Application ATP-sensitive K+ channel blocker
Boiling Point 534.9°C at 760 mmHg
Melting Point 251-255°C
Density 1.38 g/cm3
Solubility Soluble in DMSO

Reference Reading

1.Occurrence of (fluoro)quinolones and (fluoro)quinolone resistance in soil receiving swine manure for 11 years.
Xu Y1, Yu W2, Ma Q1, Zhou H1. Sci Total Environ. 2015 Oct 15;530-531:191-7. doi: 10.1016/j.scitotenv.2015.04.046. Epub 2015 May 29.
Because of the widespread use of antibiotics in animal breeding, the agricultural application of animal manure can lead to the introduction of antibiotics, antibiotic-resistant bacteria and antibiotic resistance genes to the soil and surrounding environment, which may pose a threat to public health. In this study, we investigated the status of (fluoro)quinolone (FQ) residues and FQ resistance levels in soil with and without receiving long-term swine manure. Six FQs (pipemidic acid, lomefloxacin, enrofloxacin, norfloxacin, ciprofloxacin, and ofloxacin) were only detected in manured soil, with individual concentrations ranging from below the detection limit to 27.2 μg kg(-1) and increasing with the increase in swine manure application rates. Higher load rates of swine manure yielded a higher number of ciprofloxacin-resistant (CIPr) bacteria after spreading. A total of 24 CIPr bacterial isolates were obtained from the tested soil, which belonged to four phyla (Proteobacteria, Firmicutes, Actinobacteria, and Bacteroidetes) or were related to nine different genera.
2.Prebiotic properties of galursan HF 7K on mouse gut microbiota.
Engevik MA1, Faletti CJ, Paulmichl M, Worrell RT. Cell Physiol Biochem. 2013;32(7):96-110. doi: 10.1159/000356631. Epub 2013 Dec 18.
BACKGROUND: With the rise of antibiotic resistance, new alternatives are being sought to effectively modulate the characteristics of gut microbiota to obtain pathogen resistance without the use of antibiotics. In the past, an oligosaccharide derivative of carrots, galursan HF 7K (GHF7K), has been used clinically in Austria and recently in the fowl-industry to promote health. This study examined the potential role of GHF7K as a prebiotic to alter the gut microbiota in mice.
3.Characteristics and Antibiotic Resistance of Urinary Tract Pathogens Isolated From Punjab, Pakistan.
Sohail M1, Khurshid M2, Saleem HG1, Javed H1, Khan AA3. Jundishapur J Microbiol. 2015 Jul 25;8(7):e19272. doi: 10.5812/jjm.19272v2. eCollection 2015.
BACKGROUND: Urinary tract infection (UTI) is deemed the most prevalent infectious disease in that it has now touched the overall incidence of 18/1000 persons per year in the general population.
4.Synthesis, characterization, and evaluation of the antimicrobial potential of copper(II) coordination complexes with quinolone and p-xylenyl-linked quinolone ligands.
Mjos KD1, Polishchuk E1, Abrams MJ1, Orvig C2. J Inorg Biochem. 2016 Feb 27. pii: S0162-0134(16)30052-6. doi: 10.1016/j.jinorgbio.2016.02.026. [Epub ahead of print]
The antimicrobial properties of copper have been known to mankind since the ancient times. In a coordination chemistry approach to develop novel antimicrobial agents, the quinolone antimicrobial agents ciprofloxacin (Hcipro) and pipemidic acid (Hpia), as well as dimers thereof (piperazinyl-linked with a p-xylenyl moiety) were complexed with copper(II). The synthesis and antimicrobial evaluation of bis(ciprofloxacino)copper(II) [Cu(cipro)2], bis(pipemido)copper(II) [Cu(pia)2], and the corresponding dimer complexes, [Cu2(ciproXcipro)2] and [Cu2(piaXpia)2], are reported. No combinational or synergistic effect between copper(II) and the respective quinolone ligands was observed in vitro.

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