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Pipemidic acid

Pipemidic acid structure

CAS No:
51940-44-4
Formula:
C14H17N5O3
Chemical Name:
Pipemidic acid
Synonyms:
Pyrido[2,3-d]pyrimidine-6-carboxylic acid,8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-;8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid;Pipemidic acid;Deblaston;Uromidin;Palin;Dolcol;Uroval;Pi-Coli;Urosten;Pipedac;Memento 400;Pipurin;Tractur;1489RB;Pipeacid;Uropimid;Pipemid;Filtrax;8-Ethyl-2-(piperazin-1-yl)-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid;108911-86-0;56451-79-7
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Pipemidic scid is a new antibacterial agent, is active against Pseudomonas aeruginosa.

Solid

Pipemidic acid is a pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid substituted at position 2 by a piperazin-1-yl group and at position 8 by an ethyl group. A synthetic broad-spectrum antibacterial, it is used for treatment of gastrointestinal, biliary, and urinary infections. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a monocarboxylic acid, an amino acid, a N-arylpiperazine, a pyridopyrimidine and a quinolone antibiotic.|Pipemidic Acid is a pyridopyrimidine antibiotic derivative of piromidic acid with activity against gram-negative bacteria, as well as some gram-positive bacteria. Pipemidic acid exhibits greater activity than piromidic acid or nalidixic acid and shows moderate activity against bacteria that are resistant to piromidic acid and nalidixic acid.|Antimicrobial against Gram negative and some Gram positive bacteria. It is protein bound and concentrated in bile and urine and used for gastrointestinal, biliary, and urinary infections.

Pipemidic acid Basic Attributes

Molecular Weight：

303.32

Exact Mass：

303.32

EC Number：

257-530-2

UNII：

LT12J5HVR8

NSC Number：

758160

DSSTox ID：

DTXSID3023479

NCI Thesaurus Code：

C66394

ATC Code：

J - Antiinfectives for systemic use

HScode：

29335990

Characteristics

PSA：

98.7

XLogP3：

-2.15

Appearance：

Solid

Density：

1.4±0.1 g/cm3

Melting Point：

253-255 °C

Boiling Point：

717℃

Flash Point：

>110°(230°F)

Refractive Index：

1.617

Water Solubility：

soluble in 1N sodium hydroxide or in DMSO. Insoluble in water;1 M NaOH: soluble 50mg/mL

Toxicity：

LD50 in mice (mg/kg): 4000 orally; 1000 i.p., 50 i.v. (Ficicchia)

Collision Cross Section：

171 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|174.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|185.6 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|172.63 Å² [M+H]+

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

42/43

safety instructions：

22-36/37-45

RTECS Number：

UV1153800

Marks：

Precautionary statement(s)：

P261-P280-P342 + P311

Hazard Statements：

H317-H334

GHS Classification：

|Danger|H317 (97.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 40 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

MeSH Entry Terms：

Acid, Pipemidic

Pipemidic acid Use and Manufacturing

Uses

antibacterial

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:303.32
XLogP3:-2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:3
Exact Mass:303.13313942
Monoisotopic Mass:303.13313942
Topological Polar Surface Area:98.7
Heavy Atom Count:22
Complexity:489
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethyl propionate

Trimethyl orthoformate

Urea

Diethyl sulfate

Methyl acrylate

Drug Function and Efficacy

Quinolone antibiotics interfere with bacterial DNA synthesis by acting on bacterial DNA gyrase, thus causing bacterial death. They have antibacterial effects on Gram-negative bacteria such as Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes, Proteus mirabilis, Serratia, Salmonella typhi, Shigella, Pseudomonas aeruginosa, etc.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Pimidic acid tablets
Ingredients	The main component of this product is pipemidic acid; its chemical name is: 8-ethyl-5-oxo-5,8-dihydro-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid trihydrate. Molecular formula: C14H17N5O33H2O, molecular weight: 357.37.
Indication	1. Probenecid can inhibit the renal tubular secretion of this product. When used together, the latter's blood concentration increases and the half-life is prolonged. 2. This product can reduce the clearance of caffeine from the liver, prolonging the latter's half-life. Avoid using it together, or monitor the blood concentration of caffeine. 3. This product can significantly reduce the clearance of theophylline, causing the latter's blood concentration to increase, which is prone to toxic reactions. The two should not be used together. If they need to be used together, theophylline concentration should be monitored and the dosage should be adjusted. 4. It often has a synergistic effect with gentamicin, carbenicillin, penicillin, etc.
Specifications	0.25g
Manufacturer	Guangxi Wuzhou Shennong Pharmaceutical Co., Ltd.

Pimidic acid tablets
Ingredients	The main component of this product is pipemidic acid; its chemical name is: 8-ethyl-5-oxo-5,8-dihydro-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid trihydrate. Molecular formula: C14H17N5O33H2O, molecular weight: 357.37.
Indication	1. Probenecid can inhibit the renal tubular secretion of this product. When used together, the latter's blood concentration increases and the half-life is prolonged. 2. This product can reduce the clearance of caffeine from the liver, prolonging the latter's half-life. Avoid using it together or monitor the blood concentration of caffeine. 3. This product can significantly reduce the clearance of theophylline, causing the latter's blood concentration to increase, which is prone to toxic reactions. The two should not be used together. If they need to be used together, theophylline concentration should be monitored and the dosage should be adjusted. 4. It often has a synergistic effect with gentamicin, carbenicillin, penicillin, etc.
Specifications	0.25g
Manufacturer	Harbin Pharmaceutical Group Pharmaceutical Factory No.6

Pimidic Acid Capsules
Ingredients	The main component of this product is pipemidic acid; its chemical name is: 8-ethyl-5-oxo-5,8-dihydro-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid trihydrate. Molecular formula: C14H17N5O33H2O Molecular weight: 357.37
Indication	1. Probenecid can inhibit the renal tubular secretion of this product after absorption from the wound surface. When used together, the latter's blood concentration increases and the half-life (t1/2) is prolonged. 2. This product can reduce the clearance of caffeine from the liver, prolonging the latter's half-life (t1/2). Avoid using it together, or monitor the blood concentration of caffeine. 3. This product can significantly reduce the clearance of theophylline, causing the latter's blood concentration to increase, which is prone to toxic reactions. The two should not be used together. If they need to be used together, theophylline concentration should be monitored and the dosage should be adjusted. 4. It often has a synergistic effect with gentamicin, carbenicillin, penicillin, etc.
Specifications	0.25 g
Manufacturer	Xi'an Fenghua Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Chongqing Qingyang Pharmaceutical Co., Ltd.

China
Active
Suzhou Pharmaceutical Factory

China
Active
Shandong Xinhua Pharmaceutical Company Limited

China
Active

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51940-44-4 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid

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