Drug General Information (ID: D0637)
  Drug Name
Febuxostat
  Drug Type Small molecule
  Drug Synonymous
Adenuric; TEI; Uloric; Febuxostat [USAN]; S1547; TMX 67; Tei 6720; TMX-67; Tei-6720; Uloric (TN); Febuxostat (JAN/USAN/INN); TMX-67, Adenuric, Uloric, Febuxostat; 111GE013; 2-(3-CYANO-4-ISOBUTOXY-PHENYL)-4-METHYL-5-THIAZOLE-CARBOXYLIC ACID; 2-(3-Cyano-4-(2-methylpropoxy)phenyl)-4-methylthiazole-5-carboxylic acid;2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acid; 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
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  Disease Class 5C55: Inborn purine/pyrimidine/nucleotide metabolism error
  Therapeutic Class Antihyperuricemic Agents
  Structure Could Not Find 2D Structure
3D Structure 2D Structure
  Formula C16H16N2O3S
  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
  Canonical SMILES CC1=C(SC(=N1)C2=CC(=C(C=C2)OCC(C)C)C#N)C(=O)O
  External Link
Pubchem ID 134018
CAS Number 144060-53-7
CHEBI ID 31596
TTD ID D0A5SE
INTEDE ID DR0681

Drug-Drug Interaction Network
  Sunburst Graph
AM004  Affected intra/extra-hepatic metabolism
AM006  Pharmacodynamic additive effects
BM018  Non-CYP450 enzyme inhibition
BM023  UGT induction
BM055  Increased risk of hepatotoxicity
  Relation Graph
 Full list of drugs interacting with Febuxostat
      Affected intra/extra-hepatic metabolism
   Non-CYP450 enzyme inhibition Drug Num:  6
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0136
 
Azathioprine
 
C9H7N7O2S
 
2265 
Major    Inter Info   
[1]
D1007
 
Mercaptopurine
 
C5H4N4S
 
667490 
Major    Inter Info   
[1]
D0064
 
Aminophylline
 
C16H24N10O4
 
9433 
Moderate    Inter Info   
[1]
D0544
 
Dyphylline
 
C10H14N4O4
 
3182 
Moderate    Inter Info   
[1]
D1201
 
Oxtriphylline
 
C12H21N5O3
 
656652 
Moderate    Inter Info   
[1]
D1570
 
Theophylline
 
C7H8N4O2
 
2153 
Moderate    Inter Info   
[1]
   UGT induction Drug Num:  5
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0255
 
Carbamazepine
 
C15H12N2O
 
2554 
Minor    Inter Info   
[12], [41]
D1265
 
Phenobarbital
 
C12H12N2O3
 
4763 
Minor    Inter Info   
[12], [41]
D1283
 
Phenytoin
 
C15H12N2O2
 
1775 
Minor    Inter Info   
[12], [41]
D1400
 
Rifampicin
 
C43H58N4O12
 
135398735 
Minor    Inter Info   
[12], [42]
D1415
 
Ritonavir
 
C37H48N6O5S2
 
392622 
Minor    Inter Info   
[12], [41]
      Pharmacodynamic additive effects
   Increased risk of hepatotoxicity Drug Num:  24
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0944
 
Lomitapide
 
C39H37F6N3O2
 
9853053 
Major    Inter Info   
[2]
D1073
 
Mipomersen
 
C230H324N67O122P19S19
 
118984467 
Major    Inter Info   
[3]
D1258
 
Pexidartinib
 
C20H15ClF3N5
 
25151352 
Major    Inter Info   
[4]
D1556
 
Teriflunomide
 
C12H9F3N2O2
 
54684141 
Major    Inter Info   
[5], [6], [7]
D0900
 
Leflunomide
 
C12H9F3N2O2
 
3899 
Major    Inter Info   
[5], [6], [7]
D0114
 
Asparaginase Escherichia coli
 
NA
 
NA
Moderate    Inter Info   
[8], [9], [10], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20]
D0357
 
Clofarabine
 
C10H11ClFN5O3
 
119182 
Moderate    Inter Info   
[21]
D0554
 
Efavirenz
 
C14H9ClF3NO2
 
64139 
Moderate    Inter Info   
[22], [23]
D0584
 
Epirubicin
 
C27H29NO11
 
41867 
Moderate    Inter Info   
[11], [12], [24]
D0113
 
Asparaginase Erwinia chrysanthemi
 
NA
 
NA
Moderate    Inter Info   
[8], [9], [10], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20]
D0149
 
Bedaquiline
 
C32H31BrN2O2
 
5388906 
Moderate    Inter Info   
[25]
D0199
 
Brentuximab vedotin
 
NA
 
NA
Moderate    Inter Info   
[26]
D0232
 
Calaspargase pegol
 
NA
 
NA
Moderate    Inter Info   
[8], [9], [10], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20]
D0248
 
Cannabidiol
 
C21H30O2
 
644019 
Moderate    Inter Info   
[12], [27]
D0789
 
Idelalisib
 
C22H18FN7O
 
11625818 
Moderate    Inter Info   
[28]
D1239
 
Peginterferon beta-1a
 
NA
 
NA
Moderate    Inter Info   
[29], [30], [31], [32]
D1389
 
Remdesivir
 
C27H35N6O8P
 
121304016 
Moderate    Inter Info   
[11], [12], [33], [34], [35]
D1615
 
Trabectedin
 
C39H43N3O11S
 
108150 
Moderate    Inter Info   
[12], [36]
D0826
 
Interferon beta-1a
 
NA
 
NA
Moderate    Inter Info   
[29], [30], [31], [32]
D0827
 
Interferon beta-1b
 
NA
 
NA
Moderate    Inter Info   
[29], [30], [31], [32]
D1025
 
Methotrexate
 
C20H22N8O5
 
126941 
Moderate    Inter Info   
[12], [37]
D1106
 
Naltrexone
 
C20H23NO4
 
5360515 
Moderate    Inter Info   
[38]
D1234
 
Pegaspargase
 
C14H19NO
 
436058 
Moderate    Inter Info   
[8], [9], [10], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20]
D1589
 
Tioguanine
 
C5H5N5S
 
2723601 
Moderate    Inter Info   
[39], [40]
References
1 Product Information. Uloric (febuxostat). Takeda Pharmaceuticals America, Lincolnshire, IL.
2 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
3 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
4 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
5 Canadian Pharmacists Association.
6 EMEA "EMEA public statement on leflunomide (ARAVA) - severe and serious hepatic reactions.".
7 Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
8 Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
9 Bodmer M, Sulz M, Stadlmann S, Droll A, Terracciano L, Krahenbuhl S "Fatal liver failure in an adult patient with acute lymphoblastic leukemia following treatment with L-asparaginase." Digestion 74 (2006): epub. [PMID: 16988508]
10 Cerner Multum, Inc "ANVISA Bulario Eletrnico.".
11 Cerner Multum, Inc. "Australian Product Information.".
12 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
13 Christ TN, Stock W, Knoebel RW "Incidence of asparaginase-related hepatotoxicity, pancreatitis, and thrombotic events in adults with acute lymphoblastic leukemia treated with a pediatric-inspired regimen." J Oncol Pharm Pract 24 (2018): 299-308. [PMID: 28355969]
14 Jenkins R, Perlin E "Severe hepatotoxicity from Escherichia coli L-asparaginase." J Natl Med Assoc 79 (1987): 775-9. [PMID: 3305969]
15 Lu G, Karur V, Herrington JD, Walker MG "Successful treatment of pegaspargase-induced acute hepatotoxicity with vitamin B complex and L-carnitine" Proc (Bayl Univ Med Cent) 29 (2016): 46-7. [PMID: 26722167]
16 Product Information. Asparlas (calaspargase pegol). Servier, Boston, MA.
17 Product Information. Elspar (asparaginase). Merck & Co, Inc, West Point, PA.
18 Product Information. Erwinaze (asparaginase Erwinia chrysanthemi). EUSA Pharma, Newtown, PA.
19 Product Information. Oncaspar (pegaspargase). Rhone-Poulenc Rorer, Collegeville, PA.
20 Burke PW, Aldoss I, Lunning MA, et.al "High-grade PEGylated asparaginase-related hepatotoxicity occurrence in a pediatric-inspired adult acute lymphoblastic leukemia regimen does not necessarily predict recurrent hepatotoxicity in subsequent cycles." Blood 122 (2013): 2671. [PMID: 29407583]
21 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
22 Elsharkawy AM, Schwab U, McCarron B, et al. "Efavirenz induced acute liver failure requiring liver transplantation in a slow drug metaboliser." J Clin Virol 58 (2013): 331-3. [PMID: 23763943]
23 Product Information. Sustiva (efavirenz). DuPont Pharmaceuticals, Wilmington, DE.
24 Product Information. Ellence (epirubicin) Pharmacia and Upjohn, Kalamazoo, MI.
25 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
26 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
27 Product Information. Epidiolex (cannabidiol). Greenwich Biosciences Inc, Carlsbad, CA.
28 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
29 Product Information. Avonex (interferon beta-1a). Biogen, Cambridge, MA.
30 Product Information. Betaseron (interferon beta-1b). Berlex, Richmond, CA.
31 Product Information. Plegridy (peginterferon beta-1a). Biogen Idec Inc, Cambridge, MA.
32 Product Information. Rebif (interferon beta-1a). Serono Laboratories Inc, Norwell, MA.
33 European Medicines Agency "Summary on compassionate use. Remdesivir Gilead.".
34 Gilead Sciences, Inc "About Remdesivir.".
35 US Food and Drug Administration "Fact sheet for health care providers emergency use authorization (EUA) of remdesivir (GS-5734TM)".
36 Product Information. Yondelis (trabectedin). Janssen Pharmaceuticals, Titusville, NJ.
37 Product Information. Methotrexate (methotrexate). Lederle Laboratories, Wayne, NJ.
38 Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.
39 Product Information. Aubagio (teriflunomide). Genzyme Corporation, Cambridge, MA.
40 Product Information. Tabloid (thioguanine). Prasco Laboratories, Cincinnati, OH.
41 EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
42 EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".