Pipemidic acid trihydrate

Modify Date: 2024-01-08 13:19:04

Pipemidic acid trihydrate Structure
Pipemidic acid trihydrate structure
Common Name Pipemidic acid trihydrate
CAS Number 72571-82-5 Molecular Weight 303.31600
Density 1.41g/mLat 25°C (lit.) Boiling Point 534.9ºC at 760 mmHg
Molecular Formula C14H17N5O3 Melting Point 253-255°
MSDS N/A Flash Point 277.3ºC

 Use of Pipemidic acid trihydrate


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].

 Names

Name 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid,trihydrate
Synonym More Synonyms

 Pipemidic acid trihydrate 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
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.

 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%

 Synonyms

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)