51940-44-4 Usage
Description
Pipemidic acid, a pyridopyrimidine derivative, is a potent antibiotic and cell selection agent characterized by its 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid structure. It features a piperazin-1-yl group at position 2 and an ethyl group at position 8, which contribute to its effectiveness in treating various infections.
Uses
Used in Pharmaceutical Industry:
Pipemidic acid is used as an antibiotic for treating gastrointestinal, biliary, and urinary infections. Its potent antimicrobial properties make it a valuable asset in combating bacterial infections in these areas.
Used in Research and Development:
As a cell selection agent, pipemidic acid is employed in the field of research and development, particularly in the selection and isolation of specific cell types for various experimental purposes. Its ability to selectively target cells aids in advancing scientific understanding and the development of new treatments and therapies.
Used in Antimicrobial Applications:
Pipemidic acid is also used in various antimicrobial applications, where its effectiveness in inhibiting bacterial growth is harnessed to prevent and treat infections. This makes it a versatile compound with widespread use in the medical and healthcare sectors.
Originator
Pipram ,Bellon, France ,1975
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)
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.
Check Digit Verification of cas no
The CAS Registry Mumber 51940-44-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,9,4 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 51940-44:
(7*5)+(6*1)+(5*9)+(4*4)+(3*0)+(2*4)+(1*4)=114
114 % 10 = 4
So 51940-44-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H17N5O3/c1-2-18-8-10(13(21)22)11(20)9-7-16-14(17-12(9)18)19-5-3-15-4-6-19/h7-8,15H,2-6H2,1H3,(H,21,22)
51940-44-4Relevant articles and documents
An interpenetrated bioactive nonlinear optical MOF containing a coordinated quinolone-like drug and Zn(ii) for pH-responsive release
Duan, Li-Na,Dang, Qin-Qin,Han, Cai-Yun,Zhang, Xian-Ming
, p. 1800 - 1804 (2015)
A new interpenetrated bioactive nonlinear optical metal-organic framework [Zn2(ppa)2(1,3-bdc)(H2O)] has been designed and synthesized, which shows both a high drug content of 63.9% and a good slow release effect in simulated physical conditions compared to other non-interpenetrated bioactive MOFs. It also shows a large powder second-harmonic generation (SHG) efficiency of 5.6 times that of KH2PO4 (particle size: 150-200 μm). This journal is
8-Alkyl-5-oxo-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acids and their preparation
-
, (2008/06/13)
Valuable antibacterial 8-alkyl-5-oxo-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acids, some of which are new compounds, are made from corresponding pyrimidines by a process involving condensation with an amino-ester, cyclization, halogenation, dehydrohalogenation, and saponification.
