Febuxostat Chemical Properties
- Melting point:238-239°(dec.)
- Boiling point:536.6±60.0 °C(Predicted)
- Density 1.31±0.1 g/cm3(Predicted)
- storage temp. Refrigerator
- form powder
- Merck 14,3948
- CAS DataBase Reference144060-53-7(CAS DataBase Reference)
- RTECS XJ3675310
Febuxostat Usage And Synthesis
- Indications and UsageFebuxostat is a new generation xanthine oxidase inhibitor developed by Tejin Co. (Japan,) used clinically for for long-term treatment of hyperuicemia (gout,) a new and highly effective non-purine selective inhibitor of xanthine oxidase. It is not recommended for gout patients without hyperuricemia.
- Mechanisms of ActionThe production of uric acid in the body is related to purine metabolism. In the last step of the production, hypoxanthine produces xanthine through the action of xanthine oxidoreductase (XOR), finally producing uric acid. Inhibiting the activity of this enzyme can effectively reduce the production of uric acid. Xanthine oxidase is the main enzyme promoting uric acid production. Through highly selective inhibition of oxidized and reduced xanthine oxidase, Febuxostat can reduce synthesis of uric acid, decreasing its concentration and effectively treating gout . Through liver metabolism, Xanthine oxidase does not rely on renal excretion, so patients with moderate to severe liver and kidney dysfunction do not need to reduce dosages. Febuxostat is a non-purine XOR inhibitor, so it is very safe.
- DescriptionFebuxostat, a selective xanthine oxidase inhibitor, was launched for the chronic management of hyperuricemia in patients with
gout. Hyperuricemia is defined as a serum uric acid concentration
exceeding the limit of solubility. It predisposes affected persons to
gout, a disease characterized by the formation of crystals of monosodium urate or uric acid from supersaturated fluids in joints and other
tissues. Crystal deposition is asymptomatic, but it is revealed by bouts
of joint inflammation. If left untreated, further crystals accumulate in
joints and can form deposits known as tophi. A major aim in gout
management is the long-term reduction of serum uric acid concentrations below saturation levels, as this results in crystal dissolution and
Febuxostat is a nonpurine derivative with higher potency and selectivity than allopurinol for inhibiting xanthine oxidase. It completely inhibits human xanthine oxidase activity in the lung cancer cell line A549, whereas the activities of other enzymes involved in purine or pyrimidine metabolism (e.g., purine nucleoside phosphorylase, adenosine deaminase, and pyrimidine nucleoside phosphorylase) are affected by <4%.
The incidence of adverse events such as dizziness, diarrhea, headache, and nausea with febuxostat was similar to allopurinol. Febuxostat is contraindicated in patients being treated with the xanthine oxidase substrates such as azathioprine, mercaptopurine, and theophylline. Febuxostat can be synthesized in a multistep sequence from 2,4-dicyanophenol, starting with the alkylation of the phenolic hydroxyl group with isobutyl bromide and potassium carbonate, followed by treatment with thioacetamide in hot dimethyl formamide to yield 3-cyano-4-isobutoxythiobenzamide. Cyclization of the thioamide group with 2-chloroacetoacetic acid ethyl ester in refluxing ethanol affords 2-(3-cyano-4-isoutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester, which is hydrolyzed with sodium hydroxide to produce febuxostat.
- Chemical PropertiesCrystalline Solid
- OriginatorTeijin (Japan)
- UsesXanthine oxidase/xanthine dehydrogenase inhibitor. Used for treatment of hyperuricemia and chronic gout. 40-120 mg/day febuxostat was proven effective in lowering serum urate levels when administered to manage hyperuricemia in patients with gout.
- UsesFebuxostat is primarily indicated in conditions like Gout, Hyperuricemia
- brand nameUloric, Adenuric
- ethyl 2-(4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate 4-(2-THIAZOLYL)PHENOL 2-Methoxy-5-methylbenzonitrile 4-METHYL-2-PHENYL-1,3-THIAZOLE-5-CARBOXYLIC ACID (4-METHYL-2-PHENYL-1,3-THIAZOL-5-YL)METHANOL 2-Ethoxybenzonitrile Febuxostat 5-Chloro-2-methyl-3(2H)-isothiazolone with 2-methyl-3(2H)-isothiazolone Methyl salicylate Lithium tri-tert-butoxyaluminum hydride Thiophanate-methyl Methyl bromide Ethyl cyanoformate Methyl 4-cyanobenzoate Tribenuron methyl Cyano
- Company Name:Beijing Zhongshuo Pharmaceutical Technology Development Co., Ltd Gold
- Company Name:Nanjing Gold Pharmaceutical Technology Co. Ltd. Gold
- Company Name:Beijing Mediking Biopharm Co., Ltd Gold
- Tel:15901403431 010-81769521
- Company Name:Shandong Bolode Bio-Technology Co.,ltd Gold
- Company Name:Enki Biopharmaceuticals(Shanghai) Limited Gold
- Tel:13916707528 021-57680965-