Pipemidic acid

ChemicalBook > CAS DataBase List > Pipemidic acid

Product Name: Pipemidic acid
CAS No.: 51940-44-4
Chemical Name: Pipemidic acid
Synonyms: palin;1489rb;rb1489;pipram;dolcol;xylique;pipemid;pipedac;PB-1489;deblaston
CBNumber: CB3748118
Molecular Formula: C14H17N5O3
Formula Weight: 303.32
MOL File: 51940-44-4.mol

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Pipemidic acid Property

Melting point:: 251-255℃
Boiling point:: 717℃
Density: 1.1931 (rough estimate)
refractive index: 1.7000 (estimate)
Flash point:: >110°(230°F)
storage temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
solubility: 1 M NaOH: soluble50mg/mL
pka: 4.14±0.20(Predicted)
form: Powder
color: White to off-white
Water Solubility: Soluble in 1N sodium hydroxide or in DMSO. Insoluble in water
Sensitive: Light Sensitive
CAS DataBase Reference: 51940-44-4(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 42/43
Safety Statements: 22-36/37-45
WGK Germany: 2
RTECS: UV1153800
HS Code: 29335990
Toxicity: LD50 in mice (mg/kg): 4000 orally; 1000 i.p., 50 i.v. (Ficicchia)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: P7903
Product name: Pipemidic acid
Packaging: 10g
Price: $61.2
Updated: 2024/03/01

Sigma-Aldrich

Product number: P7903
Product name: Pipemidic acid
Packaging: 100g
Price: $243.2
Updated: 2024/03/01

Alfa Aesar

Product number: J66437
Product name: Pipemidic acid, 98%
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Price: $72.65
Updated: 2024/03/01

Alfa Aesar

Product number: J66437
Product name: Pipemidic acid, 98%
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Price: $463.65
Updated: 2024/03/01

Usbiological

Product number: 288038
Product name: Pipemidic acid
Packaging: 10g
Price: $333
Updated: 2021/12/16

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Pipemidic acid Chemical Properties,Usage,Production

Chemical Properties

The substance is a light yellow crystalline powder with an odorless, bitter taste. It has a melting point range of 251-255°C, with decomposition. It is soluble in glacial acetic acid, but only slightly soluble in methanol, acetone, and DMF. It is extremely difficult to dissolve in water, ethanol, and chloroform, and is insoluble in benzene. However, it can be dissolved in dilute alkali or acid solutions.

Originator

Pipram ,Bellon, France ,1975

Uses

Pipemidic acid is a quinolone antibacterial drug that is primarily used to treat gram-negative infections of the urinary tract. It is also an antibiotic and cell selection agent. Unlike nalidixic acid, pipemidic acid has a broader spectrum of antibacterial activity and is effective for treating urinary tract and ENT infections.

Preparation

The synthesis of pipemidic acid involves a series of steps. First, ethyl 2,4-dichloropyrimidine-5-carboxylate is condensed and cyclized with ethyl β-ethylaminopropionate to yield 2-chloro-5-hydroxy-7,8-dihydro-8-ethylpyridine[2,3-d]pyrimidine-6-carboxylate. This compound is then brominated and subsequently condensed with piperazine. The resulting product is hydrolyzed and neutralized to obtain pipemidic acid.

Definition

ChEBI: 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.

Manufacturing Process

A mixture containing 1.33 g of 5,8-dihydro-8-ethyl-2-methylthio-5oxopyridol[2,3-d]pyrimidine-6-carboxylic acid, 1.94 g of piperazine hexahydrate and 20 ml of dimethyl sulfoxide was heated at 110°C for 1 hour with stirring. The separated solid was collected by filtration, washed with ethanol, and then dried at such a temperature that did not rise above 50°C to give 1.57 g of the trihydrate of the product as nearly colorless needles, MP 253° to 255°C.
The starting material may be produced by reacting 6-amino-2methylthiopyrimidine with ethoxymethylene malonic acid diethyl ester. The intermediate thus produced is converted by boiling in diphenyl ether to 6ethoxycarbonyl-2-methylthio-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine. That is hydrolyzed by sodium hydroxide to cleave the ethoxy group and then ethylated with diethyl sulfate to give the starting material.

Therapeutic Function

Antibacterial (urinary)

General Description

Chemical structure: quinolone

Pharmaceutical Applications

An orally administered pyridopyrimidine derivative with a 7-piperazinyl moiety. The piperazinyl moiety at C-7 increases in-vitro activity against Ps. aeruginosa. Pipemidic acid is inactive against Gram-positive bacteria or anaerobes
It is well absorbed orally. The drug is rapidly metabolized, primarily to acetyl, formyl and oxo derivatives, which exhibit much reduced antibacterial activity. It is eliminated in the urine, 50–85% of a dose appearing over the first 24 h, less than 2% as inactive metabolites. Non-renal clearance accounts for 10–40% of a dose in the young, rising to 40–70% in elderly subjects, thereby compensating for possible renal insufficiency. No dosage adjustment is necessary in patients with mild renal insufficiency. Some of the drug is eliminated in the bile and a significant portion appears in the feces.
Nausea and vomiting are common; dizziness, weakness and grand mal seizures have been observed, principally in the elderly. A number of reactions have been sufficiently severe to require discontinuation of therapy. Clinical use is restricted to urinary tract infections.

Biochem/physiol Actions

Pipemidic acid modulates (inhibits) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependent) DNA supercoiling, and chromosome fragmentation. Pipemidic acid has been shown to induce inhibition of lymphocyte DNA synthesis.

References

Comprehensive Heterocyclic Chemistry II Volume 7, 1996, Pages 561-624 DOI: 10.1016/B978-008096518-5.00160-X
A New Approach for Improving the Antibacterial and Tumor Cytotoxic Activities of Pipemidic Acid by Including It in Trimethyl-β-cyclodextrin doi:10.3390/ijms20020416
https://pubchem.ncbi.nlm.nih.gov/compound/Pipemidic-acid
Pipemidic Acid, a New Antibacterial Agent Active Against Pseudomonas aeruginosa: In Vitro Properties DOI: 10.1128/aac.8.2.132

Pipemidic acid Preparation Products And Raw materials

Raw materials

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester Ethyl propionate Dimethyl malonate Trimethoxymethane Urea 2,4-Dichloropyrimidine-5-carboxylic acid Methyl acrylate

Preparation Products

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View Lastest Price from Pipemidic acid manufacturers

Hebei Yanxi Chemical Co., Ltd.

Product: Pipemidic acid 51940-44-4
Price: US $40.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10 tons
Release date: 2023-09-07

Anhui Zhongda Biotechnology Co., Ltd

Product: Pipemidic acid 51940-44-4
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 100000tons
Release date: 2023-08-11

Anhui Zhongda Biotechnology Co., Ltd

Product: Pipemidic acid 51940-44-4
Price: US $90.00-70.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000/month
Release date: 2023-08-07

51940-44-4, Pipemidic acidRelated Search:

Hyaluronic acid Citric acid Folic acid Ethyl cyanoacetate Dihydromyrcenol 2,5-PYRIDINEDICARBOXYLIC ACID Ethyl 2-(Chlorosulfonyl)acetate Ethanol Quinolinic acid ISOXADIFEN-ETHYL Ethyl acetate N-Aminoethylpiperazine Pyrimidine 2-Ethylhexyl ferulate Ethylparaben Ethyl acrylate Piperacillin Ascoric Acid

8-ETHYL-5,8-DIHYDRO-5-OXO-2-[1-PIPERAZINYL]PYRIDO[2,3-D]-PYRIMIDINE-6-CARBOXYLIC ACID

LABOTEST-BB LT00772244

PIPEMIDIC ACID

1489rb

pipemid

piperamicacid

pipram

pyrido(2,3-d)pyrimidine-6-carboxylicacid,5,8-dihydro-8-ethyl-5-oxo-2-(1-piper

rb1489

xylique

8-ethyl-5-oxo-2-(1-piperazinyl)-6-pyrido[2,3-d]pyrimidinecarboxylic acid

5,8-dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxy

acideethyl-8oxo-5piperazinyl-2dihydro-5,8pyrido(2,3-d)pyrimidine-6carbo

acidopipemidico

deblaston

dolcol

palin

pipedac

Pipemidic Acid Anhydrous

8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-pyrido-(2,3-d)primidine-6-carboxylic acid

Deblaston(Madaus,Kolu)

pipemidic acid， PPA

8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylicacidtrihydrate

PB-1489

Pipemidic acid,8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acid

Pipemidic acid Solution, 1000ppm

Pyrido[2,3-d]pyriMidine-6-carboxylicacid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-

Pipemidic acid USP/EP/BP

Pipemidic Acid See P479800

Pipemidic AcidQ: What is Pipemidic Acid Q: What is the CAS Number of Pipemidic Acid Q: What is the storage condition of Pipemidic Acid

8-Ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid

C16218000 PipemidiCacid

Pipemidic acid in Methanol

51940-44-4

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