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    Chemistry

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    Also known as: 144060-53-7, Adenuric, Uloric, 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid, Tei 6720, Feburic
    Molecular Formula
    C16H16N2O3S
    Molecular Weight
    316.4  g/mol
    InChI Key
    BQSJTQLCZDPROO-UHFFFAOYSA-N
    FDA UNII
    101V0R1N2E
    Febuxostat
    A thiazole derivative and inhibitor of XANTHINE OXIDASE that is used for the treatment of HYPERURICEMIA in patients with chronic GOUT.
    Febuxostat is a Xanthine Oxidase Inhibitor. The mechanism of action of febuxostat is as a Xanthine Oxidase Inhibitor.
    1 2D Structure

    Febuxostat

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
    2.1.2 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)
    2.1.3 InChI Key
    BQSJTQLCZDPROO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(SC(=N1)C2=CC(=C(C=C2)OCC(C)C)C#N)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    101V0R1N2E
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic Acid

    2. 6720, Tei

    3. Tei 6720

    4. Tei-6720

    5. Tei6720

    6. Uloric

    2.3.2 Depositor-Supplied Synonyms

    1. 144060-53-7

    2. Adenuric

    3. Uloric

    4. 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic Acid

    5. Tei 6720

    6. Feburic

    7. Tei-6720

    8. Tmx 67

    9. Tmx-67

    10. 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic Acid

    11. Zurig

    12. C16h16n2o3s

    13. Febuxostat (uloric)

    14. Nsc-758874

    15. 2-(3-cyano-4-isobutoxy-phenyl)-4-methyl-5-thiazole-carboxylic Acid

    16. Chembl1164729

    17. 101v0r1n2e

    18. 5-thiazolecarboxylic Acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-

    19. Febuxostat [usan]

    20. Ncgc00182059-02

    21. Dsstox_cid_28576

    22. Dsstox_rid_82848

    23. Dsstox_gsid_48650

    24. 5-thiazolecarboxylic Acid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-

    25. Smr002529566

    26. Uloric (tn)

    27. Cas-144060-53-7

    28. 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid

    29. 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic Acid

    30. Donifoxate

    31. Febuxostatum

    32. Febuday

    33. Goturic

    34. Febric

    35. Goutex

    36. Febuxostat (jan/usan/inn)

    37. Febuxostat [usan:inn:ban]

    38. Unii-101v0r1n2e

    39. Febuxostat- Bio-x

    40. Feburic (tn)

    41. Spiramycinadipate

    42. 111ge013

    43. Febuxostat [mi]

    44. Febuxostat [inn]

    45. Febuxostat [jan]

    46. S1547

    47. Febuxostat [vandf]

    48. 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methylthiazole-5-carboxylic Acid

    49. Febuxostat [mart.]

    50. Febuxostat [who-dd]

    51. Febuxostat,uloric, Tmx-67

    52. Mls004774136

    53. Mls006011568

    54. Febuxostat [ema Epar]

    55. Schembl249339

    56. Gtpl6817

    57. Zinc5423

    58. Thyl-thiazole-5-carboxylic Acid

    59. Dtxsid8048650

    60. Febuxostat [orange Book]

    61. Febuxostat, >=98% (hplc)

    62. Chebi:31596

    63. Bcpp000233

    64. Hms3264c20

    65. Hms3655c03

    66. Hms3673m21

    67. Hms3743i09

    68. Hms3868j03

    69. Mx-67

    70. Pharmakon1600-01504286

    71. Act06289

    72. Bcp02342

    73. Wzb81950

    74. Tox21_113004

    75. Ac-425

    76. Bbl036503

    77. Bdbm50320491

    78. Fd7322

    79. Mfcd00871598

    80. Nsc758874

    81. Stl559020

    82. Akos015841695

    83. Tox21_113004_1

    84. Bcp9000679

    85. Bs-1018

    86. Ccg-213303

    87. Cs-0403

    88. Db04854

    89. Nsc 758874

    90. Pb33929

    91. 2-(3-cyano-4-isobutoxy-phenyl)-4-me

    92. Ncgc00182059-03

    93. Bc164443

    94. Hy-14268

    95. Am20090760

    96. F0847

    97. Ft-0601639

    98. Sw219283-1

    99. D01206

    100. Ab01274796-01

    101. Ab01274796_02

    102. Ab01274796_03

    103. 060f537

    104. Q417296

    105. Sr-01000940023

    106. Q-100164

    107. Sr-01000940023-2

    108. Brd-k48367671-001-01-8

    109. Z1550648761

    110. 2-(3-cyano-4-isobutyloxy)-phenyl-4-methyl-5-thiazolecarboxylic Acid

    111. 2-(3-cyano-4-isobutoxyphenyl)-4-methyl- 1,3-thiazole-5-carboxylic Acid

    112. 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 316.4 g/mol
    Molecular Formula C16H16N2O3S
    XLogP33.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass316.08816355 g/mol
    Monoisotopic Mass316.08816355 g/mol
    Topological Polar Surface Area111 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity448
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameUloric
    PubMed HealthFebuxostat (By mouth)
    Drug ClassesAntigout
    Drug LabelULORIC (febuxostat) is a xanthine oxidase inhibitor. The active ingredient in ULORIC is 2-[3-cyano-4-(2-methylpropoxy) phenyl]-4-methylthiazole-5-carboxylic acid, with a molecular weight of 316.38. The empirical formula is C16H16N2O3S.The chemical st...
    Active IngredientFebuxostat
    Dosage FormTablet
    RouteOral
    Strength80mg; 40mg
    Market StatusPrescription
    CompanyTakeda Pharms Usa

    2 of 2  
    Drug NameUloric
    PubMed HealthFebuxostat (By mouth)
    Drug ClassesAntigout
    Drug LabelULORIC (febuxostat) is a xanthine oxidase inhibitor. The active ingredient in ULORIC is 2-[3-cyano-4-(2-methylpropoxy) phenyl]-4-methylthiazole-5-carboxylic acid, with a molecular weight of 316.38. The empirical formula is C16H16N2O3S.The chemical st...
    Active IngredientFebuxostat
    Dosage FormTablet
    RouteOral
    Strength80mg; 40mg
    Market StatusPrescription
    CompanyTakeda Pharms Usa

    4.2 Drug Indication

    Febuxostat is indicated for the chronic management of hyperuricemia in adult patients with gout who have an inadequate response to a maximally titrated dose of [allopurinol], who are intolerant to allopurinol, or for whom treatment with allopurinol is not advisable. It is not recommended for the treatment of asymptomatic hyperuricemia or secondary hyperuricemia.

    FDA Label

    Febuxostat Mylan is indicated for the prevention and treatment of hyperuricaemia in adult patients undergoing chemotherapy for haematologic malignancies at intermediate to high risk of Tumor Lysis Syndrome (TLS).

    Febuxostat Mylan is indicated for the treatment of chronic hyperuricaemia in conditions where urate deposition has already occurred (including a history, or presence of, tophus and/or gouty arthritis ).

    Febuxostat Mylan is indicated in adults.

    Febuxostat Krka is indicated for the treatment of chronic hyperuricaemia in conditions where urate deposition has already occurred (including a history, or presence of, tophus and/or gouty arthritis ).

    Febuxostat Krka is indicated in adults.

    80 mg strength:

    - Treatment of chronic hyperuricaemia in conditions where urate deposition has already occurred (including a history, or presence of, tophus and/or gouty arthritis ).

    - Adenuric is indicated in adults.

    120 mg strength:

    - Adenuric is indicated for the treatment of chronic hyperuricaemia in conditions where urate deposition has already occurred (including a history, or presence of, tophus and/or gouty arthritis ).

    - Adenuric is indicated for the prevention and treatment of hyperuricaemia in adult patients undergoing chemotherapy for haematologic malignancies at intermediate to high risk of Tumor Lysis Syndrome (TLS).

    - Adenuric is indicated in adults.

    Prevention of hyperuricaemia

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Febuxostat is a novel, selective xanthine oxidase/dehydrogenase inhibitor that works by decreasing serum uric acid in a dose-dependent manner. In healthy subjects, febuxostat decreased the mean serum uric acid and serum xanthine concentrations, as well as the total urinary uric acid excretion. Febuxostat at daily doses of 40-80 mg reduced the 24-hour mean serum uric acid concentrations by 40 to 55%. Closely related to the drug-induced reduction of serum uric acid levels and mobilization of urate crystals in tissue deposits, febuxostat is associated with gout flares. Unlike [allopurinol] and [oxypurinol], febuxostat has no inhibitory actions against other enzymes involved in purine and pyrimidine synthesis and metabolism, because it does not structurally resemble purines or pyrimidines.

    5.2 MeSH Pharmacological Classification

    Gout Suppressants

    Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout. (See all compounds classified as Gout Suppressants.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    FEBUXOSTAT
    5.3.2 FDA UNII
    101V0R1N2E
    5.3.3 Pharmacological Classes
    Xanthine Oxidase Inhibitors [MoA]; Xanthine Oxidase Inhibitor [EPC]
    5.4 ATC Code

    M04AA03

    M04AA03

    M04AA03

    M04AA03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    M - Musculo-skeletal system

    M04 - Antigout preparations

    M04A - Antigout preparations

    M04AA - Preparations inhibiting uric acid production

    M04AA03 - Febuxostat

    5.5 Absorption, Distribution and Excretion

    Absorption

    After oral administration, about 85% of febuxostat is absorbed rapidly. Tmax ranges from 1 to 1.5 hours. Following once-daily oral administration, Cmax was approximately 1.6 0.6 mcg/mL at a dose of 40 mg febuxostat and 2.6 1.7 mcg/mL at a dose of 80 mg febuxostat. A high-fat meal decreased Cmax by 49% and AUC by 18%, but there were no clinically significant changes in the ability of febuxostat to decrease serum uric acid concentrations.

    Route of Elimination

    Febuxostat is eliminated via both hepatic and renal pathways. Following oral administration of 80 mg radiolabeled febuxostat, approximately 49% of the dose was recovered in the urine. In urine, about 3% of the recovered dose accounted for unchanged febuxostat, 30% accounted for the acyl glucuronide metabolite, 13% accounted for oxidative metabolites and their conjugates, and 3% accounted for unidentified metabolites. Approximately 45% of the total dose was recovered in the feces, where 12% of the dose accounted for the unchanged parent drug. About 1% accounted for the acyl glucuronide metabolite, 25% accounted for oxidative metabolites and their conjugates, and 7% accounted for unidentified metabolites.

    Volume of Distribution

    The apparent steady-state volume of distribution (Vss/F) of febuxostat ranges from 29 to 75 L, indicating a low to medium volume of distribution.

    Clearance

    Following oral administration of single doses of 10 to 240 mg, the mean apparent total clearance ranged from 10 to 12 L/h.

    5.6 Metabolism/Metabolites

    Febuxostat is metabolized in the liver by UDP-glucuronosyltransferase (UGT) and Cytochrome P450 (CYP) enzymes, with the relative contribution of each enzyme isoform in the metabolism of febuxostat not fully elucidated. UGT1A1, UGT1A3, UGT1A9, and UGT2B7 mediate conjugation of febuxostat, which approximately accounts for 2244% of the metabolism of the total dose administered, to produce the acyl-glucuronide metabolite. CYP1A2, CYP2C8, CYP2C9, and non-P450 enzymes are responsible for the oxidation reaction, which accounts for 2-8% of the metabolism of the dose. Oxidation reaction produces 67M-1, 67M-2, and 67M-4, which are pharmacologically active metabolites. 67M-1, 67M-2, and 67M-4 can further undergo glucuronidation and sulfation. Hydroxy metabolites are present in human plasma at much lower concentrations than the parent drug.

    5.7 Biological Half-Life

    The apparent mean terminal elimination half-life of approximately 5 to 8 hours.

    5.8 Mechanism of Action

    Gout is a form of acute arthritis that is characterized by the accumulation of crystals of monosodium urate and urate crystals in or around a joint, leading to inflammation and persistent urate crystal deposition in bones, joints, tissues, and other organs that may exacerbate over time. Hyperuricemia is closely related to gout, whereby it may exist for many years before the first clinical attack of gout; thus, aberrated serum uric acid levels and hyperuricemia are believed to be the biochemical aberration involved in the pathogenesis of gout. Xanthine oxidoreductase (XOR) can act as a xanthine oxidase or xanthine dehydrogenase. In humans, it is a critical enzyme for uric acid production as it catalyzes the oxidation reaction steps from hypoxanthine to xanthine and from xanthine to uric acid in the pathway of purine metabolism. Febuxostat potently inhibits XOR, blocking both its oxidase and dehydrogenase activities. With high affinity, febuxostat binds to XOR in a molecular channel leading to the molybdenum-pterin active site, where [allopurinol] demonstrates relatively weak competitive inhibition. XOR is mainly found in the dehydrogenase form under normal physiological conditions; however, in inflammatory conditions, XOR can be converted into the xanthine oxidase form, which catalyzes reactions that produce reactive oxygen species (ROS), such as peroxynitrite. ROS contribute to vascular inflammation and alterations in vascular function. As febuxostat can inhibit both forms of XOR, it can inhibit ROS formation, oxidative stress, and inflammation. In a rat model, febuxostat suppressed renal ischemia-reperfusion injury by attenuating oxidative stress.

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    13-Jan-2021
    26-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DOSAGE - TABLET;ORAL - 40MG

    USFDA APPLICATION NUMBER - 21856

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    DOSAGE - TABLET;ORAL - 80MG

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