Febuxostat

Febuxostat Struktur
144060-53-7
CAS-Nr.
144060-53-7
Englisch Name:
Febuxostat
Synonyma:
FBX;Uloric;Febuxostat Impurity;2-(3-cyano-4-isobutoxyphenyl);TMX 67;CS-1598;Tei-6720;NSC63871;Febrista;Adenuric
CBNumber:
CB4841564
Summenformel:
C16H16N2O3S
Molgewicht:
316.37
MOL-Datei:
144060-53-7.mol

Febuxostat Eigenschaften

Schmelzpunkt:
238-239°(dec.)
Siedepunkt:
536.6±60.0 °C(Predicted)
Dichte
1.31±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
powder
pka
2.48±0.10(Predicted)
Farbe
White to Off-White
Merck 
14,3948
InChI
InChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)
InChIKey
BQSJTQLCZDPROO-UHFFFAOYSA-N
SMILES
S1C(C(O)=O)=C(C)N=C1C1=CC=C(OCC(C)C)C(C#N)=C1
CAS Datenbank
144060-53-7(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
RTECS-Nr. XJ3675310
HS Code  2934.10.2000
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P330 Mund ausspülen.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Febuxostat Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Febuxostat, 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 eventual disappearance.
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%.

Chemische Eigenschaften

Crystalline Solid

Physikalische Eigenschaften

Febuxostat has low solubility. It is almost insoluble in acidic conditions, slightly soluble in neutral conditions, and slightly more soluble in alkaline conditions. It is not suitable for making injections, but it can be taken orally because of its high oil-water partition coefficient and strong ability to cross cell membranes.

Verwenden

Febuxostat 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. 40-120 mg/day febuxostat was proven effective in lowering serum urate levels when administered to manage hyperuricemia in patients with gout. It is not recommended for gout patients without hyperuricemia.

synthetische

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.

Allgemeine Beschreibung

Febuxostat is a potent, non-purine compound, which inhibits the expression of cytokines/chemokines. It has also been reported to inhibit LPS-induced TNF-α, VCAM-1, MMP9 and MCP-1 expression.

Clinical Use

Fabuxostat was discovered by Teijin Pharmaceuticals and licensed to TAP Pharmaceuticals (which is currently part of Takeda Pharmaceuticals) and was approved in the U.S. for the treatment of hyperuricemia in patients with gout. It is a once-daily non-purine based agent with potent inhibitory activity against xanthine oxidase. The safety profile of the drug also does not require dose adjustment for patients with mild to moderate renal or hepatic impairment. Febuxostat is the first new agent cleared for this indication in 40 years.

Nebenwirkungen

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.

Mode of action

Xanthine oxidase is the main enzyme promoting uric acid production. It works by non-competitively blocking the molybdenum pterin center, which is the active site of xanthine oxidase. Through highly selective inhibition of oxidized and reduced xanthine oxidase, Febuxostat can reduce the 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.

Febuxostat Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Febuxostat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 858)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
SHANDONG BOYUAN PHARMACEUTICAL CO., LTD.
+86-0531-69954981 +8615666777973
dwyane.wang@boyuanpharm.com China 211 58
shan dong Fengjin Pharmaceutical company
+8615066764791
liangfulin@fengjin-pharma.com China 8 58
JUYE XIANDAI fine chemistry Co.,Ltd
+86-18958038633; +8618958038633
tony@sdhypharma.com China 64 58
Hebei Mojin Biotechnology Co., Ltd
+8613288715578
sales@hbmojin.com China 12470 58
Zibo Hangyu Biotechnology Development Co., Ltd
+86-0533-2185556 +8617865335152
Mandy@hangyubiotech.com China 11013 58
Anhui Ruihan Technology Co., Ltd
+8617756083858
daisy@anhuiruihan.com China 994 58
Shanghai Affida new material science and technology center
+undefined15081010295
admin@oudaxin.com China 371 58
hebei hongtan Biotechnology Co., Ltd
+86-86-1913198-3935 +8617331935328
sales03@chemcn.cn China 952 58
Ouhuang Engineering Materials (Hubei) Co., Ltd
+8617702722807
admin@hbouhuang.com China 3001 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806
sales@capotchem.com China 29797 60

144060-53-7()Verwandte Suche:


  • Febuxostat (Uloric)
  • Febuxostat (TEI-6720)
  • Febuxostat Tablets
  • FEBUXOSTAT API
  • Febuxostat (This product is unavailable in the U.S.)
  • Febuxostat Tabletshehe
  • Febuxostat 2-[3-Cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid
  • Febuxostat, >=99%
  • Febuxostat IMP
  • Tei-6720
  • 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
  • 2-[3-Cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid
  • 2-(3-Cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic Acid
  • 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid
  • TMX 67
  • FEBUXOSTAT
  • Febuxosta
  • Febuxostat Impurity V
  • Febuxostat(ThisproductisunavailableintheU.S.)>
  • 5-Thiazolecarboxylic acid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-
  • Febuxostat A
  • Fubuxostat
  • 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylicaci
  • Febuxostat USP/EP/BP
  • Febuxostat Working std
  • Febuxostat (A/C crystal)
  • FebuxostatQ: What is Febuxostat Q: What is the CAS Number of Febuxostat Q: What is the storage condition of Febuxostat Q: What are the applications of Febuxostat
  • NSC63871
  • NSC 63871
  • NSC-63871
  • CS-1598
  • TEI 6720 - Febuxostat
  • FBX
  • Uloric
  • Febuxostat Impurity
  • 2-(3-cyano-4-isobutoxyphenyl)
  • The cloth sutent
  • Febrista
  • Fesotan *
  • Febuxostat( China GMP )
  • 2-(3-Cyano-4-isobutoxyphenyl)-4-methylthiazol-5-carboxylic acid
  • Febuxostat CRS
  • Febuxostat 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5- carboxylic acid
  • Febuxostat Form-A, C & G
  • Adenuric
  • Febuxostat Reference Standard
  • 144060-53-7
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  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • eterocycles
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