30652-13-2

Usage

Explanation

This is the chemical name of the compound, also known as deferiprone.

Explanation

Deferiprone is classified as a chelating agent because it binds to metal ions, specifically excess iron in the body.

Explanation

Deferiprone is used to treat iron overload by binding to excess iron and promoting its excretion, thus reducing the risk of organ damage.

Explanation

Deferiprone is commonly prescribed for patients with thalassemia, a genetic blood disorder that often requires frequent blood transfusions, leading to iron overload.

Explanation

Deferiprone is available in tablet form, making it easy for patients to take as prescribed.

Explanation

While deferiprone is generally well-tolerated, some patients may experience mild side effects such as gastrointestinal upset.

Explanation

Deferiprone plays a crucial role in managing iron overload and mitigating its potential complications in patients with certain medical conditions.

Classification

Chelating agent

Medical use

Treatment of iron overload

Target patient population

Patients with thalassemia

Form

Tablet

Side effects

Generally well-tolerated, mild gastrointestinal upset in some patients

Role

Managing iron overload and mitigating potential complications

InChI:InChI=1/C9H13NO2/c1-3-5-10-6-4-8(11)9(12)7(10)2/h4,6,12H,3,5H2,1-2H3

Upstream product

• 51807-73-9 1-propylammonium acetate 
• 130752-64-6 Acetic acid 5-acetoxy-1-methyl-2-oxo-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclopent-3-enyl ester 
• 138548-48-8 5,6-Dihydro-3,5-dihydroxy-1-n-propyl-4H-pyridone 
• 90037-24-4 3-Benzyloxy-2-methyl-1-(propyl)-pyridin-4(1H)-one 
• 107-10-8 propylamine 
• 118-71-8 Maltol 
• 82756-28-3 3-(β-D-galactopyranosyloxy)-2-furanyl methyl ketone 
• 3420-59-5 isomaltol 
• 61049-69-2 3-O-benzylmaltol 
• 24822-33-1 D-isomaltose 
• 24404-57-7 glucose-6-phosphate sodium salt 
• 20675-63-2 6-O-benzyl-D-galactose 

Relevant academic research and scientific papers

Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxypyridine-4-one and 3-hydroxypyran-4-one derivatives

A series of Mannich bases of 2-alkyl-3-hydroxy-pyridine-4-ones, namely 2-alkyl-3-hydroxy-5-N-piperidylmethyl or N,N-dialkylaminomethyl pyridine-4-ones 9, 10 and 15-18, two derivatives of N-aryl-2-methyl-3-hydroxy-pyridine-4-ones 19, 20 and two N-alkyl derivatives of maltol, 21 and 22 were prepared. They were screened for their antibacterial and antifungal activities against a variety of microorganisms using micro plate Alamar Blue assay (MABA) method. Multiple linear regressions (MLR) analysis was performed for the synthesized compounds as well as a series of pyridinone and pyranone derivatives 23-43 which have been synthesized and evaluated for antimicrobial activity by other researchers previously. Studied compounds showed a better quantitative structure-activity relationship (QSAR) model for the antimicrobial activity against Candida albicans and Staphylococcus aureus in comparison with other tested microorganisms.

Efficient syntheses of N-alkyl-3-hydroxy-2-methyl-4(1H)-pyridinones from carbohydrate precursors

N-alkyl-3-hydroxy-2-methyl-4(1H)-pyridinones can be synthesised in reasonable yield from either 1-(3-hydroxy-2-furanyl)ethanone or O- galactosylisomaltol. Since these carbohydrate precursors can be produced from the disaccharide, α-D-lactose, a simple and inexpensive transformation into pyridinones is possible.

Synthesis and in vitro trypanocidal activity of some novel iron chelating agents

This report describes the syntheses and in vitro trypanocidal activity of a number of iron(III) chelators against epimastigotes of Trypanosoma cruzi. The compounds examined included a number of lipophilic N-alkyl derivatives of 2-ethyl- and 2-methyl-3-hydroxypyrid-4-ones, N,N'-bis(o-hydroxybenzyl)-(±)-trans-1,2-diaminocyclohexane, cyclotetrachromotropylene and four commercially available carboxy derivatives of pyridine, pyrazine, and pyarazole. Benznidazole, the drug clinically used in the treatment of Chagas' disease in humans, served as standard. All compounds were screened in vitro against Trypanosoma cruzi epimastigotes at 50 and 100 μg/ml for 72 h of exposure. At 100 μg/ml dosage, at least 4 compounds exhibited high epimastigote growth inhibition (65-69%) comparable to benznidazole (72%), whereas 9 compounds showed moderate to fair activity (53-64%) in the in vitro assay. At the lower concentration (50 μg/ml), the inhibitory activity of the best of these compounds was reduced significantly (39-48%) compared to the standard drug (59%). The activity of all the carboxylic acids remained in the lower range (4-25%). It is hypothesized that the enhanced activity of some of the compounds is due to their increased lipophilicity which enables them to successfully pass through the cellular membrane of Trypanosoma cruzi epimastigotes. The trypanocidal activities of the most effective compounds were significantly reduced when tested in the presence of added ferric ion.

Synthesis of N-Substituted 3-Hydroxy-2-methyl-4-pyridones and -pyridonimines

Carbohydrates with 1,4-glycoside bonds like maltose, lactose, dextrin or strach react with primary amines as well as amino acids or proteins to give i.e. 3-hydroxy-2-methyl-4-pyridones 5 and 3-hydroxy-2-methyl-4-pyridonimines 7.A generally applicable synt

5,6-Dihydro-3,5-dihydroxy-4H-pyridones - A new maillard products from 6-O-substituted hexoses and primary amines

From reaction mixtures of n-propylamine and 6-O-substituted hexoses 1 (glucose-6-phosphate, isomaltose, 6-O-benzylgalactose) a previously unknown Maillard product, the 5,6-dihydro-3,5-dihydroxy-1-n-propyl-4H-pyridone (7a) was isolated in yields up to 20%.

Formation of 4, 5-dihydroxy-2-α-D-glucopyranosyloxy-5-methyl-2-cyclopenten-1-one in the maillard reaction of maltose

Among other products, 4,5-dihydroxy-2-α-D-glucopyranosyloxy-5-methyl-2-cyclopenten-1-one is formed in warming an aqueous solution of piperidinomaltulose.

Process for producing pyrid-4-ones

Substituted-3-hydroxy-pyrid-4-ones, derivatives thereof, and salts thereof are produced by reacting subsituted-3-hydroxypyr-4-one with ammonia or a non-sterically hindered primary amine usually in the presence of a solvent such as water. Also disclosed are novel derivatives of 2-ethyl-3-hydroxypyrid-4-one.

New synthetic approach and iron chelating studies of 1-alkyl-2-methyl-3-hydroxypyrid-4-ones

The major diseases of iron metabolism are iron deficiency anaemia, which could be treated using Fe2+ or Fe3+ salt supplements, and iron overload, which could arise either from an increased gastrointestinal absorption of iron or from recurrent blood transfusions. While the former form of iron overload could be treated by phlebotomy the latter requires the use of a chelator. Desferrioxamine is the only clinically available chelator for the treatment of iron overload but its use worldwide is limited because it is expensive and orally inactive. Several α-ketohydroxy heteroaromatic chelators have been synthesised and tested for their iron binding properties at physiological pH. The synthetic route involves the benzylation of the hydroxyl group of maltol using benzyl chloride, the conversion of the benzylated maltol to the 1-alkyl benzylated pyridine derivative by introducing the corresponding alkylamine in alkaline conditions and the cleavage of the benzyl group in acid to form the 1-alkyl-2-methyl-3-hydroxypyrid-4-one. All the chelators are water soluble and stable at a wide range of pH, forming stable, water soluble, coloured iron complexes with a molar ratio of approximately 3 chelator:1 iron at pH 7.4 and lower molar ratio of chelators to iron complexes at acidic pH. When the 1-methyl, 1-ethyl and 1-propyl, -2-methyl-3-hydroxypyrid-4-ones were mixed at pH 7.4 with transferrin, ferritin and haemosiderin substantial amounts of iron were released. The low cost of synthesis, the strong iron binding properties of these chelators and their other in vitro and in vivo iron mobilising effects increase the prospects of their use in many aspects of iron metabolism and the possible treatment of related diseases particularly iron overload.

Iron complexes of hydroxy pyridones useful for treating iron deficiency anemia

Pharmaceutical compositions containing an iron complex of a 3-hydroxypyrid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic hydrocarbon group and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are also replaced by an aliphatic hydrocarbon group, are of value for the treatment of iron deficiency anemia.