PIPEMIDIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H17N5O3
Molecular Weight	303.3165
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(N=C2)N3CCNCC3

InChI

InChIKey=JOHZPMXAZQZXHR-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C14H17N5O3
Molecular Weight	303.3165
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/810076 | http://www.druginfosys.com/Drug.aspx?drugCode=967&type=1 | http://www.toku-e.com/product/pipemidic_acid/

Pipemidic Acid is a quinolone antibacterial agent. It’s used in the treatment of urinary tract infections, recidive cystitis, prolongation of the therapy of pyelonephritis (prolonged therapy at patients with tendency to recidives. It belongs to DNA Gyrase inhibitor pharmacological group on the basis of mechanism of action and also classified in Antibacterial pharmacological group. Pipemidic acid is contraindicated at conditions of proved hypersensitivity, severe renal and hepatic insufficiency, cirrhosis of the liver, porphyria, diseases of the central nervous system (epilepsy and neurological conditions with low level for convulsions). Pipemidic acid is contraindicated at children and adolescents at growing phase.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial DNA gyrase 2 Target ID: bacterial DNA gyrase Sources: http://www.toku-e.com/product/pipemidic_acid/	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.druginfosys.com/Drug.aspx?drugCode=967&type=1	Primary	Basic research	LINAPIN Approved Use Unknown
Dysenteries 2 Sources: http://www.druginfosys.com/Drug.aspx?drugCode=967&type=1	Primary	Basic research	LINAPIN Approved Use Unknown
Enteritis 5 Sources: http://www.druginfosys.com/Drug.aspx?drugCode=967&type=1	Primary	Basic research	LINAPIN Approved Use Unknown

PubMed

Title	Date	PubMed
Quantitation of fluoroquinolones in honey using tandem mass spectrometry (LC-MS/MS): nested validation with two mass spectrometers.	2010-12-15	21140677
Oxidation of fluoroquinolone antibiotics and structurally related amines by chlorine dioxide: Reaction kinetics, product and pathway evaluation.	2010-12	20708211
Poly[bis-[8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxyl-ato]cadmium].	2010-10-31	21588905
Dispersive liquid-liquid microextraction combined with nonaqueous capillary electrophoresis for the determination of fluoroquinolone antibiotics in waters.	2010-10	20859952
The role of host factors and bacterial virulence genes in the development of pyelonephritis caused by Escherichia coli in renal transplant recipients.	2010-07	20448070
Altered blood glucose concentration is associated with risk of death among patients with community-acquired Gram-negative rod bacteremia.	2010-06-22	20569435
[Food additive urisan in combined treatment of urolithiasis].	2010-03-10	20213910
Optimization of a pipemidic acid autotaxin inhibitor.	2010-02-11	20041668
Poly[bis-[μ(2)-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxyl-ato]nickel(II)].	2010-01-09	21579609
Simultaneous determination of proline and pipemidic acid in human urine by capillary electrophoresis with electrochemiluminescence detection.	2010	20872568
A capillary zone electrophoretic method for simultaneous determination of seven drugs in pharmaceuticals and in human urine.	2009-11-18	19916376
Poly[[bis-[μ(2)-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxyl-ato]cobalt(II)] dihydrate].	2009-10-10	21578091
Poly[[bis-[μ(2)-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxyl-ato]zinc(II)] dihydrate].	2009-09-19	21577745
Diabetes does not affect outcome in patients with Enterobacteriaceae bacteremia.	2009-06-13	19523241
[Determination of DNA using Eu-PPA as fluorescence probe by time-resolved fluorescence].	2009-06	19810540
Prophylactic ciprofloxacin treatment prevented high mortality, and modified systemic and intestinal immune function in tumour-bearing rats receiving dose-intensive CPT-11 chemotherapy.	2009-05-19	19401694
Enhanced permeability of the urinary bladder wall: the role of polymer charge.	2009-04	19435140
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009-03	19680903
Ultra performance liquid chromatography tandem mass spectrometry performance evaluation for analysis of antibiotics in natural waters.	2009-03	19148627
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009-01	19449537
Synthesis, characterization, antibacterial and anti-inflammatory activities of enoxacin metal complexes.	2009	19657456
Trace analysis of quinolone and fluoroquinolone antibiotics from wastewaters by liquid chromatography-electrospray tandem mass spectrometry.	2008-12-19	19007934
Intravesical treatments of bladder cancer: review.	2008-07	18369709
Poly[[bis-[μ(2)-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxyl-ato]manganese(II)] dihydrate].	2008-03-14	21202004
Comparative study of the antimutagenic properties of vitamins C and E against mutation induced by norfloxacin.	2008-02-11	18267022
Heparin decreases permeability of pig urinary bladder wall preliminarily enhanced by chitosan.	2008-02	18302041
Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter.	2007-12	17939016
Major complications and associated risk factors of transrectal ultrasound guided prostate needle biopsy: a retrospective study of 1875 cases in taiwan.	2007-11	18063514
Adsorption and oxidation of fluoroquinolone antibacterial agents and structurally related amines with goethite.	2007-01	17083963
Structure and medium effects on the photochemical behavior of nonfluorinated quinolone antibiotics.	2006-11-30	17132068
Diclofenac in the management of E. coli urinary tract infections.	2006-11-10	17091768
Electrochemiluminescence determination of pipemidic acid using sulfite as energy transfer mediator.	2006-10-15	16908137
Distribution characteristics of orally administered olamufloxacin, a newly synthesized fluoroquinolone antibacterial, in lung epithelial lining fluid and alveolar macrophage in rats.	2006-10	16875808
Kinetic model of drug distribution in the urinary bladder wall following intravesical instillation.	2006-09-28	16806751
Antimicrobial susceptibility of pathogens isolated from adult patients with uncomplicated community-acquired urinary tract infections in the Russian Federation: two multicentre studies, UTIAP-1 and UTIAP-2.	2006-08	16829055
Determination of quinolone residues in chicken and fish by capillary electrophoresis-mass spectrometry.	2006-06	16736458
Liver initiation activity of norfloxacin but not nalidixic acid, pipemidic acid, and ciprofloxacin on in vivo short-term liver initiation assay in rats.	2006-05-15	16580113
Synthesis and spectroscopic study of copper(II) and manganese(II) complexes with pipemidic acid.	2006-03-01	15996512
Genotoxic potential of quinolone antimicrobials in the in vitro comet assay and micronucleus test.	2006-02-28	16384725
Efficient approach for the reliable quantification and confirmation of antibiotics in water using on-line solid-phase extraction liquid chromatography/tandem mass spectrometry.	2006-01-20	16309690
T cell-mediated hypersensitivity to quinolones: mechanisms and cross-reactivity.	2006-01	16393267
Antibiotic susceptibility of potentially probiotic vaginal lactobacilli.	2006	17485797
Multicommuted optosensor for the determination of pipemidic acid in biological fluids.	2005-12-15	16259938
Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide.	2005-06-15	16047783
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.	2005-05	16004377
Micellar electrokinetic chromatography for determination of drug partition in phospholipids.	2005-01	15652373
[A study on europium sensitized chemiluminescence of pipemidic acid].	2004-12	15828315
Responsiveness of genetically epilepsy-prone rats to aminophylline-induced seizures and interactions with quinolones.	1991-02	1851545
Screening for new compounds with antiherpes activity.	1984-10	6517562

Patents

Sample Use Guides

In Vivo Use Guide

2 capsules of 200 mg two times daily, or 1 film coated tablet of 400 mg two times daily, during the period of 10 days.

Route of Administration: Oral

In Vitro Use Guide

Pipemidic acid is active against gram-negative bacteria including Pseudomonas aeruginosa as well as some gram-positive bacteria. The activity of pipemidic acid is scarcely affected by the addition of serum, sodium cholate, or change of medium pH, but is subject to the influence of inoculum size. Its action is bactericidal above minimal inhibitory concentrations.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:44:42 GMT 2025` Edited by `admin` on `Wed Apr 02 08:44:42 GMT 2025`
Record UNII	LT12J5HVR8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PIPEMIDIC ACID

Official Name

English

FILTRAX

Preferred Name

English

NURIL

Brand Name

English

PYRIDO(2,3-D)PYRIMIDINE-6-CARBOXYLIC ACID, 8-ETHYL-5,8-DIHYDRO-5-OXO-2-(1-PIPERAZINYL)-

Common Name

English

PIPEMIDATE

Common Name

English

pipemidic acid [INN]

Common Name

English

8-ETHYL-5,8-DIHYDRO-5-OXO-2-(1-PIPERAZINYL)PYRIDO(2,3-D)PYRIMIDINE-6-CARBOXYLIC ACID

Systematic Name

English

PIPURIN

Brand Name

English

UROPIMID

Brand Name

English

Pipemidic acid [WHO-DD]

Common Name

English

PIPEACID

Brand Name

English

PIPEMIDIC ACID [MART.]

Common Name

English

UROSTEN

Brand Name

English

PIPEMIDIC ACID ANHYDROUS

Common Name

English

PIPEDAC

Brand Name

English

NSC-758160

Code

English

PI-COLI

Brand Name

English

PIPEMID

Brand Name

English

TRACTUR

Brand Name

English

PIPEMIDIC ACID [JAN]

Common Name

English

PIPEMIDIC ACID [MI]

Common Name

English

UROVAL

Brand Name

English

MEMENTO 400

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C255