Pipemidic acid

Structural formula
General
Surname	Pipemidic acid
other names	Piperamidic acid; Pipemidic acid; 8-Ethyl-5,8-dihydro-5-oxo-2- (piperazin-1-yl) pyrido [2,3- d ] pyrimidine-6-carboxylic acid;
Molecular formula	C 14 H 17 N 5 O 3
External identifiers / databases
EC number	257-530-2
ECHA InfoCard	100.052.283
PubChem	4831
ChemSpider	4665
DrugBank	DB13823
Wikidata	Q754986
Drug information
ATC code	J01 MB04
Drug class	Antibiotic , quinolone
Mechanism of action	Gyrase inhibitors
properties
Molar mass	303.32 g mol −1
Physical state	firmly
Melting point	253-255 ° C
solubility	little in water (322 mg l −1 at 23 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 317-334
	P: 261-280-284-304 + 340-342 + 311
Toxicological data	529 mg kg −1 ( LD 50 , rat , iv ) ; 16 g kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pipemidic acid is a synthetically produced chemical compound from the group of pyridopyrimidines . The compound is a gyrase inhibitor and is therefore used as a chemotherapy drug for urinary tract infections . Pipemidic acid is structurally similar to quinolones ; Compared to nalidixic acid , it has - in addition to a further nitrogen atom in the secondary ring ( pyrimidine ) - an additional piperazine substituent.

history

In 1974 Dainippon Pharmaceutics received the patent on pipemidic acid. In Europe, the antibiotic is available under the trade name Deblaston ( Madaus ).

Properties and side effects

Pipemidic acid is only minimally soluble in water (322 mg · l ⁻¹ at 23 ° C) and is therefore mainly used in the form of the more soluble meglumine salt or the trihydrate for urinary tract infections. Disorders of the gastrointestinal tract and allergic reactions can occur as side effects. Its use is contraindicated for children and pregnant women.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on pipemidic acid. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2017.
↑ ^a ^b Data sheet pipemidic acid from Sigma-Aldrich , accessed on November 11, 2017 ( PDF ).
↑ ^a ^b Pipemidic acid in the Lexicon of Biology, Spektrum.de.

[roempp-1] ↑ ^a ^b ^c ^d ^e ^f Entry on pipemidic acid. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2017.

[Sigma-2] Data sheet pipemidic acid from Sigma-Aldrich , accessed on November 11, 2017 ( PDF ).

[spektrum-3] Pipemidic acid in the Lexicon of Biology, Spektrum.de.