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Merck
CN

P7903

Pipemidic acid

Synonym(s):

8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C14H17N5O3
CAS Number:
51940-44-4
Molecular Weight:
303.32
NACRES:
NA.85
PubChem Substance ID:
24898889
UNSPSC Code:
51282938
EC Number:
257-530-2
MDL number:
MFCD00057291

Key Documents

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InChI key

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)

SMILES string

CCN1C=C(C(O)=O)C(=O)c2cnc(nc12)N3CCNCC3

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

DNA synthesis | interferes
cell wall synthesis | interferes
enzyme | inhibits

Gene Information

human ... CYP1A2(1544)

Analysis Note

Very slightly soluble in water. It dissolves in diluted solutions of acids and of alkali hydroxides.

Application

Pipemidic acid is used to study DNA damage and mutagenic activity. It has been used to induce articular lesions in the neonatal mouse and is used to study human lymphocyte blastogenesis and γ-interferon production .

Biochem/physiol Actions

Pipemidic acid modulates (inhibits) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependent) DNA supercoiling, and chromosome fragmentation. Pipemidic acid has been shown to induce inhibition of lymphocyte DNA synthesis.

General description

Chemical structure: quinolone

Other Notes

10g,100g
Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000203132
0000203132
0000135966
0000085644
089M4806V

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D A Schmid et al.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology, 36(1), 59-69 (2006-01-06)
Quinolones are widely used, broad spectrum antibiotics that can induce immediate- and delayed-type hypersensitivity reactions, presumably either IgE or T cell mediated, in about 2-3% of treated patients. To better understand how T cells interact with quinolones, we analysed six
Margherita Lavorgna et al.
International journal of molecular sciences, 20(2) (2019-01-24)
Pipemidic acid (HPPA) is a quinolone antibacterial agent used mostly to treat gram-negative infections of the urinary tract, but its therapeutic use is limited because of its low solubility. Thus, to improve drug solubility, natural cyclodextrins (CDs) are used for
Yao-Dong Liang et al.
Analytical and bioanalytical chemistry, 380(7-8), 918-923 (2004-11-30)
A flow-injection chemiluminescence (CL) method for the determination of pipemidic acid is described. It is based on energy transfer from excited state peroxynitrous acid to pipemidic acid, in which the excited state peroxynitrous acid is synthesized on-line by the mixing
Juan Li et al.
Environmental health perspectives, 120(8), 1144-1149 (2012-05-10)
Inappropriate use of antibiotics in swine feed could cause accelerated emergence of antibiotic resistance genes, and agricultural application of swine waste could spread antibiotic resistance genes to the surrounding environment. We investigated the distribution of plasmid-mediated quinolone resistance (PMQR) genes
Jin Sun et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 64(2), 238-245 (2006-08-01)
This study described distribution characteristics of olamufloxacin (HSR-903) in lung epithelial lining fluid (ELF) and alveolar macrophage (AM) in rats, two important representative infectious sites in lower respiratory tract infections. The rats were orally administered at a dose of 10mg/kg.
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