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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
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%
Packaging
10g
Price
$72.65
Updated
2024/03/01
Alfa Aesar
Product number
J66437
Product name
Pipemidic acid, 98%
Packaging
100g
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

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Pipemidic acid Suppliers

Hubei widely chemical technology Co., Ltd.
Tel
027-83991130 18627774460
Fax
027-83991130
Email
1718093273@qq.com
Country
China
ProdList
1890
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58
XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-0712-2580635 15527768850
Email
1791901229@qq.com
Country
China
ProdList
8850
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52
Tianjin heowns Biochemical Technology Co., Ltd.
Tel
400 638 7771
Email
sales@heowns.com
Country
China
ProdList
14443
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57
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9823
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79
Hunan Hui Bai Shi Biotechnology Co., Ltd.
Tel
0731-85526065 13308475853
Email
ivy@hnhbsj.com
Country
China
ProdList
4531
Advantage
62
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12338
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7553
Advantage
61
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 18521732826;
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
24835
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65
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4863
Advantage
58
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
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View Lastest Price from Pipemidic acid manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
Pipemidic acid 51940-44-4
Price
US $40.00-40.00/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

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