7460. Pipemidic Acid

Nomenclature

CAS number: 51940-44-4
8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid; piperamic acid; 1489-RB; Filtrax (Biomed. Foscama); Memento 400 (Volpino); Pi-Coli (Ist. Vitamine); Pipeacid (SIT); Pipedac (Teofarma); Pipemid (Gentili); Pipurin (Brocchieri); Tractur (Damor); Uropimid (CT); Urosten (Bonomelli); Uroval (Firma).
C14H17N5O3; mol wt 303.32.
C 55.44%, H 5.65%, N 23.09%, O 15.82%.

Description and references

Quinolone antibacterial. Prepn: S. Minami et al., DE 2341146; eidem, US 3887557 (1974, 1975 both to Dainippon Pharm.); Pesson et al., C. R. Seances Acad. Sci. Ser. C 278, 1169 (1974); De Lajudie et al., C. R. Seances Acad. Sci. Ser. D 279, 1931 (1974); Matsumoto, Minami, J. Med. Chem. 18, 74 (1975). Characterization: Ficicchia, Farmaco Ed. Prat. 30, 207 (1974). Antibacterial activity: Ficicchia, De Lajudie, ibid. 252. Pharmacology: Shimizu et al., Antimicrob. Agents Chemother. 7, 441 (1975).

Chemical structure

Properties

Yellowish-white, odorless, bitter-tasting crystals, mp 253-255°. Hygroscopic. Yellows slowly in light. Sol in acid soln and alkaline. Very slightly sol in water, alcohol; slightly sol in chloroform (0.5%), methanol (0.4%). Practically insol in ether, benzene. LD50 in mice (mg/kg): 4000 orally; 1000 i.p., 50 i.v. (Ficicchia).

Derivative

Trihydrate.

Nomenclature

CAS number: 72571-82-5
Deblaston (Madaus); Dolcol (Dainippon); Pipram (RPR); Solupemid (Recordati).

Properties

Nearly colorless needles, mp 253-255°.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs