Pipemidic acid trihydrate

Names

[ Name ]:
Pipemidic acid trihydrate

[Synonym ]:
Pipemidic acid hydrate (JP16)
8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acid 3H2-O
Pipemidic acid trihydrate
Pyrido(2,3-d)pyrimidine-6-carboxylic acid,5,8-dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)-,trihydrate
C14H17N5O3.3H2O
Karunomazin (TN)

Biological Activity

[Description]:

Pipemidic acid trihydrate, a derivative of Piromidic acid, is an antibacterial agent. Pipemidic acid trihydrate inhibits DNA gyrase. Pipemidic acid trihydrate is active against gram-negative bacteria including Pseudomonas aeruginosa as well as some gram-positive bacteria. Pipemidic acid trihydrate can be used for the research of intestinal, urinary, and biliary tract infections[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Pipemidic acid trihydrate 是 DNA 促旋酶的抑制剂，DNA 促旋酶是一种催化 ATP 依赖性 DNA 负超螺旋的细菌酶[2]。

[In Vivo]

Pipemidic acid (50 mg/kg) trihydrate 口服吸收良好，在小鼠、大鼠、犬、猴中血浆峰浓度范围为 4~12 μg/mL[3]。 Pipemidic acid trihydrate 在小鼠单次口服后的平均致死剂量超过 16000 mg/kg[3]。

[References]

[1]. Iacovino R, et al. β-Cyclodextrin inclusion complex to improve physicochemical properties of pipemidic acid: characterization and bioactivity evaluation. Int J Mol Sci. 2013 Jun 25;14(7):13022-41.

[2]. Aoyama H, et, al. Purification of Citrobacter freundii DNA gyrase and inhibition by quinolones. Antimicrob Agents Chemother. 1988 Jan;32(1):104-9.

[3]. Shimizu M, et, al. Pipemidic acid: absorption, distribution, and excretion. Antimicrob Agents Chemother. 1975 Apr;7(4):441-6.

Chemical & Physical Properties

[ Density]:
1.41g/mLat 25°C (lit.)

[ Boiling Point ]:
534.9ºC at 760 mmHg

[ Melting Point ]:
253-255°

[ Molecular Formula ]:
C₁₄H₁₇N₅O₃

[ Molecular Weight ]:
303.31600

[ Flash Point ]:
277.3ºC

[ Exact Mass ]:
303.13300

[ PSA ]:
100.35000

[ LogP ]:
0.31300

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Very slightly soluble in water and in methylene chloride, practically insoluble in ethanol (96 per cent). It dissolves in dilute solutions of acids and of alkali hydroxides.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UV1153850

CHEMICAL NAME :: Pyrido(2,3-d)pyrimidine-6-carboxylic acid, 5,8-dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)-, trihydrate

CAS REGISTRY NUMBER :: 72571-82-5

LAST UPDATED :: 199609

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C14-H17-N5-O3.3H2-O

MOLECULAR WEIGHT :: 357.42

WISWESSER LINE NOTATION :: T66 BN DN GV JNJ HVQ J2 C- DT6M DNTJ &QH 3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1635 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 575 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1274 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 610 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,634,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,232,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1213 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,232,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 529 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,232,1979 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 200 mg/kg/2D-I

TOXIC EFFECTS :: Behavioral - ataxia Musculoskeletal - joints

REFERENCE :: 85ISAN "Modern Pharmaceuticals of Japan, VI," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Association 1981 Volume(issue)/page/year: -,9-94,1981

Safety Information

[ RTECS ]:
UV1153850

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%