19562-30-2 Usage
Description
Piromidic acid is a quinolone antibiotic that exhibits potent activity against a wide range of Gram-positive and Gram-negative bacteria, including Staphylococcus aureus and Escherichia coli. It possesses antimalarial properties and is effective against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum, as well as hepatic stages of Plasmodium yoelii yoelii. The compound works by inhibiting the growth of nalidixic acid-sensitive strains of E. coli in an in vitro model of bacterial cystitis and is characterized by its ability to act as a topoisomerase II inhibitor.
Uses
Used in Pharmaceutical Industry:
Piromidic acid is used as an antibacterial agent for treating various bacterial infections. Its broad-spectrum activity against both Gram-positive and Gram-negative bacteria, including S. aureus and E. coli, makes it a valuable asset in the fight against bacterial infections.
Used in Antimalarial Applications:
Piromidic acid is used as an antimalarial agent for combating chloroquine-sensitive and -resistant strains of P. falciparum. Its effectiveness against hepatic stages of P. yoelii yoelii also contributes to its potential as a therapeutic option in the treatment of malaria.
Used in Bacterial Cystitis Treatment:
Piromidic acid is used as a therapeutic agent for treating bacterial cystitis, a urinary tract infection caused by bacteria such as E. coli. It inhibits the growth of nalidixic acid-sensitive strains of E. coli in an in vitro model, demonstrating its potential in managing and treating this condition.
Used as a Topoisomerase II Inhibitor:
Piromidic acid is used as a topoisomerase II inhibitor, which plays a crucial role in the regulation of DNA replication, transcription, and repair. By inhibiting this enzyme, piromidic acid can disrupt essential cellular processes in bacteria, contributing to its antibacterial activity.
Originator
Panacid, Dainippon, Japan ,1972
Manufacturing Process
150 mg of 6-carboxy-5,8-dihydro-8-ethyl-2-methylthio-5-oxopyrido[2,3d]pyrimidine was added to 30 ml of absolute ethanol containing 1.1 g of dissolved pyrrolidine, and the mixture was reacted for 5 hours at 95°C in a sealed tube. The solvent was removed by distillation, and the residue was recrystallized from methanol-chloroform. There were obtained 111 mg of 6carboxy-5,8-dihydro-8-ethyl-5-oxo-2-pyrrolidino-pyrido[2,3-d]pyrimidine having a MP of 314° to 316°C.The starting material is produced by reacting 6-amino-2-methylthiopyrimidine with ethoxymethylene malonic acid diethyl ester. That intermediate is thermally treated in diphenyl ether to give 6-ethoxycarbonyl-2-methylthio-5oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine. The ethoxy group is hydrolyzed off with sodium hydroxide and one nitrogen is ethylated with diethyl sulfate to give the starting material. These are the same initial steps as used in the pipemidic acid syntheses earlier in this volume.
Therapeutic Function
Antibacterial (urinary)
Pharmaceutical Applications
A pyrimidopyrimidine derivative with a C7-pyrrolidinyl ring, allowing a slight increase in activities against Gram-positive cocci. Its main antibacterial activity is close to that of nalidixic acid and there have been reports of renal toxicity. It is available in only a few countries.
Safety Profile
Poison by subcutaneous and intravenous routes. Moderately toxic by skin contact and intraperitoneal routes. An antibacterial agent. When heated to decomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 19562-30-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,5,6 and 2 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 19562-30:
(7*1)+(6*9)+(5*5)+(4*6)+(3*2)+(2*3)+(1*0)=122
122 % 10 = 2
So 19562-30-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H16N4O3/c1-2-17-8-10(13(20)21)11(19)9-7-15-14(16-12(9)17)18-5-3-4-6-18/h7-8H,2-6H2,1H3,(H,20,21)
19562-30-2Relevant articles and documents
Process for the preparation of 4-chloro-5-alkoxycarbonyl-2-methoxy-pyrimidines
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, (2008/06/13)
Process for the preparation of a 4-chloro-5-alkoxycarbonyl-2-methoxy-pyrimidine of the formula: STR1 IN WHICH R1 is a lower alkyl radical with 1 to 4 carbon atoms, which comprises the following stages: A) condensation of a salt of O-methylisourea and an inorganic or organic acid, with an alkyl alkoxymethylenemalonate STR2 in an aqueous medium and in the presence of an excess of an alkali metal hydroxide, to form the corresponding salt of the 5-alkoxycarbonyl-4-hydroxy-2-methoxy-pyrimidine, and neutralization of the said salt by the addition of an inorganic or organic acid, in order to liberate this 5-alkoxycarbonyl-4-hydroxy-2-methoxy-pyrimidine, and STR3 B) bringing the latter compound, suspended in dimethylformamide, into contact with thionyl chloride, at room temperature, in order to form the corresponding 4-chloro-5-alkoxycarbonyl-2-methoxy-pyrimidine: STR4
