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Chemistry

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Also known as: 49562-28-9, Procetofen, Lipantil, Tricor, Lipanthyl, Antara
Molecular Formula
C20H21ClO4
Molecular Weight
360.8  g/mol
InChI Key
YMTINGFKWWXKFG-UHFFFAOYSA-N
FDA UNII
U202363UOS

Fenofibrate
An antilipemic agent which reduces both CHOLESTEROL and TRIGLYCERIDES in the blood.
Fenofibrate is a Peroxisome Proliferator Receptor alpha Agonist. The mechanism of action of fenofibrate is as a Peroxisome Proliferator-activated Receptor alpha Agonist.
1 2D Structure

Fenofibrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
2.1.2 InChI
InChI=1S/C20H21ClO4/c1-13(2)24-19(23)20(3,4)25-17-11-7-15(8-12-17)18(22)14-5-9-16(21)10-6-14/h5-13H,1-4H3
2.1.3 InChI Key
YMTINGFKWWXKFG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)Cl
2.2 Other Identifiers
2.2.1 UNII
U202363UOS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Antara Micronized Procetofen

2. Apo Feno Micro

3. Apo Fenofibrate

4. Apo-feno-micro

5. Apo-fenofibrate

6. Azu, Fenofibrat

7. Cil

8. Controlip

9. Debat, Fnofibrate

10. Durafenat

11. Fnofibrate Debat

12. Fnofibrate Msd

13. Fenobeta

14. Fenofanton

15. Fenofibrat Abz

16. Fenofibrat Al

17. Fenofibrat Azu

18. Fenofibrat Fph

19. Fenofibrat Heumann

20. Fenofibrat Hexal

21. Fenofibrat Ratiopharm

22. Fenofibrat Stada

23. Fenofibrat Von Ct

24. Fenofibrat-ratiopharm

25. Gen Fenofibrate

26. Gen-fenofibrate

27. Heumann, Fenofibrat

28. Hexal, Fenofibrat

29. Lf 178

30. Lf-178

31. Lf178

32. Lipanthyl

33. Lipantil

34. Liparison

35. Lipidil

36. Lipidil Ter

37. Lipidil-ter

38. Livesan

39. Lofibra

40. Micronized Procetofen, Antara

41. Mtw Fenofibrat

42. Mtw-fenofibrat

43. Normalip

44. Novo Fenofibrate

45. Novo-fenofibrate

46. Nu Fenofibrate

47. Nu-fenofibrate

48. Phenofibrate

49. Pms Fenofibrate Micro

50. Pms-fenofibrate Micro

51. Procetofen

52. Procetofen, Antara Micronized

53. Procetofene

54. Secalip

55. Stada, Fenofibrat

56. Supralip

57. Tricor

2.3.2 Depositor-Supplied Synonyms

1. 49562-28-9

2. Procetofen

3. Lipantil

4. Tricor

5. Lipanthyl

6. Antara

7. Lipidil

8. Fenobrate

9. Secalip

10. Triglide

11. Fenoglide

12. Finofibrate

13. Lipoclar

14. Lipofene

15. Proctofene

16. Fenogal

17. Lipirex

18. Lipofen

19. Sedufen

20. Elasterin

21. Fenotard

22. Protolipan

23. Ankebin

24. Lipidex

25. Lipifen

26. Liposit

27. Lipsin

28. Nolipax

29. Fenofibratum [inn-latin]

30. Propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate

31. Fenofibrato [inn-spanish]

32. Lipantil (tn)

33. Tricor (tn)

34. Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

35. Lf-178

36. Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionate

37. 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic Acid 1-methylethyl Ester

38. Nsc 281319

39. Fenofibrate Micronized

40. Isopropyl (4'-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate

41. Fnf

42. Propanoic Acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, 1-methylethyl Ester

43. Elasterate

44. Procetofene

45. Luxacor

46. Mfcd00133314

47. Fenofibrate Delayed Release

48. Chembl672

49. Mls000028515

50. Chebi:5001

51. Isopropyl 2-(p-(p-chlorobenzoyl)phenoxy)-2-methylpropionate

52. Isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate

53. Lofibra

54. U202363uos

55. Propanoic Acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-, 1-methylethyl Ester

56. Nsc-281319

57. Ncgc00015437-10

58. Fenofibrato

59. Fenofibratum

60. Smr000058299

61. Supralip

62. Cas-49562-28-9

63. Dsstox_cid_9874

64. Propan-2-yl 2-{4-[(4-chlorophenyl)carbonyl]phenoxy}-2-methylpropanoate

65. Dsstox_rid_78828

66. Dsstox_gsid_29874

67. Tricor (micronized)

68. Antara (micronized)

69. Fenomax

70. Isopropyl 2-[p-(p-chlorobenzoyl)phenoxy]-2-methylpropionate

71. Pharmavit

72. Fenofibrate (micronized)

73. Fulcro

74. Cip-fenofibrate

75. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic Acid 1-methylethyl Ester

76. Lcp-fenochol

77. Lcp-feno

78. Triglide (tn)

79. Fenofibrate Idd-p

80. Lipofen (tn)

81. Antara (tn)

82. Ccris 7282

83. Sr-01000000091

84. Einecs 256-376-3

85. Lf 178

86. Brn 2062462

87. Procetoken

88. Isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionate

89. Unii-u202363uos

90. Hsdb 7736

91. Fenofibrate,(s)

92. Grs-027

93. Fenofibrate [usan:usp:inn:ban]

94. Prestwick_217

95. Spectrum_001250

96. Opera_id_328

97. Fenofibrate [mi]

98. Prestwick0_000275

99. Prestwick1_000275

100. Prestwick2_000275

101. Prestwick3_000275

102. Spectrum2_001390

103. Spectrum3_001431

104. Spectrum4_000413

105. Spectrum5_001479

106. Fenofibrate [inn]

107. Fenofibrate [jan]

108. Lopac-f-6020

109. Fenofibrate [hsdb]

110. Fenofibrate [usan]

111. Ec 256-376-3

112. F 6020

113. Fenofibrate [vandf]

114. Schembl4670

115. Fenofibrate [mart.]

116. Lopac0_000486

117. Bspbio_000150

118. Bspbio_003162

119. Fenofibrate [usp-rs]

120. Fenofibrate [who-dd]

121. Kbiogr_000706

122. Kbioss_001730

123. Mls001148191

124. Mls002548878

125. Bidd:gt0574

126. Divk1c_000557

127. Fenofibrate (jan/usp/inn)

128. Spectrum1501010

129. Spbio_001380

130. Spbio_002369

131. Fenofibrate [ema Epar]

132. Fenofibrate, >=99%, Powder

133. Bpbio1_000166

134. Fenofibrate (tricor, Trilipix)

135. Gtpl7186

136. Dtxsid2029874

137. Hms501l19

138. Kbio1_000557

139. Kbio2_001730

140. Kbio2_004298

141. Kbio2_006866

142. Kbio3_002382

143. Fenofibrate [orange Book]

144. Ninds_000557

145. Fenofibrate [ep Monograph]

146. Fenofibrate [usp Impurity]

147. Hms1568h12

148. Hms1921b17

149. Hms2090g20

150. Hms2092b05

151. Hms2095h12

152. Hms2231b14

153. Hms3259k03

154. Hms3261b13

155. Hms3369m13

156. Hms3649d20

157. Hms3655k12

158. Hms3712h12

159. Isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate

160. Pharmakon1600-01501010

161. Zinc584092

162. Fenofibrate [usp Monograph]

163. Albb-028958

164. Bcp21243

165. Tox21_110147

166. Tox21_300151

167. Tox21_500486

168. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic Acid Isopropyl Ester

169. Bdbm50085042

170. Ccg-38996

171. Nsc281319

172. Nsc757822

173. S1794

174. Akos005107777

175. Tox21_110147_1

176. Ab03716

177. Ac-4227

178. Cs-0892

179. Db01039

180. Lp00486

181. Ms-2223

182. Nc00452

183. Nsc-757822

184. Sdccgsbi-0050470.p004

185. Idi1_000557

186. Ncgc00015437-01

187. Ncgc00015437-02

188. Ncgc00015437-03

189. Ncgc00015437-04

190. Ncgc00015437-05

191. Ncgc00015437-06

192. Ncgc00015437-07

193. Ncgc00015437-08

194. Ncgc00015437-09

195. Ncgc00015437-11

196. Ncgc00015437-12

197. Ncgc00015437-13

198. Ncgc00015437-14

199. Ncgc00015437-16

200. Ncgc00015437-17

201. Ncgc00015437-31

202. Ncgc00021475-03

203. Ncgc00021475-04

204. Ncgc00021475-05

205. Ncgc00021475-06

206. Ncgc00021475-07

207. Ncgc00021475-08

208. Ncgc00253945-01

209. Ncgc00261171-01

210. Fenofibrate (micronized) (fenofibrate

211. Fenofibrate, Analytical Reference Material

212. Hy-17356

213. Sy052561

214. Sbi-0050470.p003

215. Db-051642

216. Ab00052196

217. Eu-0100486

218. F0674

219. Ft-0626400

220. Ft-0654669

221. Sw196525-4

222. C07586

223. D00565

224. Ab00052196-15

225. Ab00052196-16

226. Ab00052196_17

227. Ab00052196_18

228. 562f289

229. A827746

230. Q419724

231. Q-201111

232. Sr-01000000091-2

233. Sr-01000000091-5

234. Sr-01000000091-6

235. Sr-01000000091-8

236. Brd-k50388907-001-05-6

237. Brd-k50388907-001-18-9

238. Brd-k50388907-001-20-5

239. Sr-01000000091-16

240. Z2768724415

241. Fenofibrate, European Pharmacopoeia (ep) Reference Standard

242. Isopropyl 2-(4-(4-chlorobenzoyl)-phenoxy)-2-methylpropanoate

243. 1-methylethyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate

244. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoicacidisopropylester

245. Fenofibrate, United States Pharmacopeia (usp) Reference Standard

246. Isopropyl (4''-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate

247. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic Acid 1-methyl-ethyl Ester

248. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic Acid Isopropyl Ester

249. Fenofibrate, Pharmaceutical Secondary Standard; Certified Reference Material

250. Isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate;fenofibrate

251. Propanoic Acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, 1-methylethylester

2.3.3 Other Synonyms

1. 42017-89-0

2. Fenofibric Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 360.8 g/mol
Molecular Formula C20H21ClO4
XLogP35.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass360.1128368 g/mol
Monoisotopic Mass360.1128368 g/mol
Topological Polar Surface Area52.6 Ų
Heavy Atom Count25
Formal Charge0
Complexity458
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 16  
Drug NameAntara
PubMed HealthFenofibrate (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelFenofibrate, is a lipid regulating agent available as tablets for oral administration. Each tablet contains 54 mg or 160 mg of fenofibrate, USP. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoic acid, 1-methylethy...
Active IngredientFenofibrate
Dosage FormCapsule
RouteOral
Strength43mg; 130mg; 30mg; 90mg
Market StatusPrescription
CompanyLupin Atlantis

2 of 16  
Drug NameFenofibrate
PubMed HealthFenofibrate (By mouth)
Drug ClassesAntihyperlipidemic
Active IngredientFenofibrate
Dosage FormCapsule
RouteOral
Strength43mg; 200mg; 130mg; 67mg; 134mg
Market StatusPrescription
CompanyMylan Pharms; Teva; Apotex; Dr Reddys Labs Sa; Impax Labs

3 of 16  
Drug NameFenofibrate
PubMed HealthFenofibric acid (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelFENOGLIDE (fenofibrate) Tablets, is a lipid regulating agent available as tablets for oral administration. Each tablet contains 40 mg or 120 mg fenofibrate. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl) phenoxy]-2-methyl-propanoic acid,...
Active IngredientFenofibrate
Dosage FormTablet; Capsule
Routeoral; Oral
Strength43mg; 160mg; 54mg; 48mg; 130mg; 107mg; 145mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Ranbaxy; Valeant Intl; Teva; Lupin; Mylan; Impax Labs

4 of 16  
Drug NameFenoglide
Drug LabelLIPOFEN (fenofibrate capsules, USP), is a lipid regulating agent available as hard gelatin capsules for oral administration. Each hard gelatin capsule contains 50 or 150 mg of fenofibrate, USP. The chemical name for fenofibrate is 2-[4-(4-chloroben...
Active IngredientFenofibrate
Dosage FormTablet
RouteOral
Strength120mg; 40mg
Market StatusPrescription
CompanySantarus

5 of 16  
Drug NameFibricor
Drug LabelTRICOR (fenofibrate tablets), is a lipid regulating agent available as tablets for oral administration. Each tablet contains 48 mg or 145 mg of fenofibrate. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl) phenoxy]-2-methyl-propanoic acid,...
Active IngredientFenofibric acid
Dosage FormTablet
RouteOral
Strength105mg; 35mg
Market StatusPrescription
CompanyMutual Pharm

6 of 16  
Drug NameLipofen
Drug Label Triglide (fenofibrate) Tablets, is a lipid regulating agent available as tablets for oral administration. Each tablet contains 50 mg or 160 mg of fenofibrate. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl) phenoxy] 2-methyl-pr...
Active IngredientFenofibrate
Dosage FormCapsule
RouteOral
Strength150mg; 50mg
Market StatusPrescription
CompanyCipher Pharms

7 of 16  
Drug NameTricor
Active IngredientFenofibrate
Dosage FormTablet
RouteOral
Strength145mg; 48mg
Market StatusPrescription
CompanyAbbvie

8 of 16  
Drug NameTriglide
Active IngredientFenofibrate
Dosage FormTablet
RouteOral
Strength160mg
Market StatusPrescription
CompanySkyepharma Ag

9 of 16  
Drug NameAntara
PubMed HealthFenofibrate (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelFenofibrate, is a lipid regulating agent available as tablets for oral administration. Each tablet contains 54 mg or 160 mg of fenofibrate, USP. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoic acid, 1-methylethy...
Active IngredientFenofibrate
Dosage FormCapsule
RouteOral
Strength43mg; 130mg; 30mg; 90mg
Market StatusPrescription
CompanyLupin Atlantis

10 of 16  
Drug NameFenofibrate
PubMed HealthFenofibrate (By mouth)
Drug ClassesAntihyperlipidemic
Active IngredientFenofibrate
Dosage FormCapsule
RouteOral
Strength43mg; 200mg; 130mg; 67mg; 134mg
Market StatusPrescription
CompanyMylan Pharms; Teva; Apotex; Dr Reddys Labs Sa; Impax Labs

11 of 16  
Drug NameFenofibrate
PubMed HealthFenofibric acid (By mouth)
Drug ClassesAntihyperlipidemic
Drug LabelFENOGLIDE (fenofibrate) Tablets, is a lipid regulating agent available as tablets for oral administration. Each tablet contains 40 mg or 120 mg fenofibrate. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl) phenoxy]-2-methyl-propanoic acid,...
Active IngredientFenofibrate
Dosage FormTablet; Capsule
Routeoral; Oral
Strength43mg; 160mg; 54mg; 48mg; 130mg; 107mg; 145mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Ranbaxy; Valeant Intl; Teva; Lupin; Mylan; Impax Labs

12 of 16  
Drug NameFenoglide
Drug LabelLIPOFEN (fenofibrate capsules, USP), is a lipid regulating agent available as hard gelatin capsules for oral administration. Each hard gelatin capsule contains 50 or 150 mg of fenofibrate, USP. The chemical name for fenofibrate is 2-[4-(4-chloroben...
Active IngredientFenofibrate
Dosage FormTablet
RouteOral
Strength120mg; 40mg
Market StatusPrescription
CompanySantarus

13 of 16  
Drug NameFibricor
Drug LabelTRICOR (fenofibrate tablets), is a lipid regulating agent available as tablets for oral administration. Each tablet contains 48 mg or 145 mg of fenofibrate. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl) phenoxy]-2-methyl-propanoic acid,...
Active IngredientFenofibric acid
Dosage FormTablet
RouteOral
Strength105mg; 35mg
Market StatusPrescription
CompanyMutual Pharm

14 of 16  
Drug NameLipofen
Drug Label Triglide (fenofibrate) Tablets, is a lipid regulating agent available as tablets for oral administration. Each tablet contains 50 mg or 160 mg of fenofibrate. The chemical name for fenofibrate is 2-[4-(4-chlorobenzoyl) phenoxy] 2-methyl-pr...
Active IngredientFenofibrate
Dosage FormCapsule
RouteOral
Strength150mg; 50mg
Market StatusPrescription
CompanyCipher Pharms

15 of 16  
Drug NameTricor
Active IngredientFenofibrate
Dosage FormTablet
RouteOral
Strength145mg; 48mg
Market StatusPrescription
CompanyAbbvie

16 of 16  
Drug NameTriglide
Active IngredientFenofibrate
Dosage FormTablet
RouteOral
Strength160mg
Market StatusPrescription
CompanySkyepharma Ag

4.2 Therapeutic Uses

Fenofibrate is used as an adjunct to dietary therapy to decrease elevated serum total and LDL-cholesterol, triglyceride, and apo B concentrations, and to increase HDL-cholesterol concentrations in the management of primary hypercholesterolemia and mixed dyslipidemia, including heterozygous familial hypercholesterolemia and other causes of hypercholesterolemia.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1731


Fenofibrate also is used as an adjunct to dietary therapy in the management of patients with elevated serum triglyceride concentrations. Efficacy of the drug in reducing the risk of pancreatitis in patients with marked elevations in triglyceride concentrations (i.e., greater than 2000 mg/dL) has not been established. Fenofibrate is not indicated for use in patients with type I hyperlipoproteinemia who have elevated triglyceride and chylomicron concentrations but normal VLDL-cholesterol concentrations.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1732


/EXPL THER/ Inflammation is implicated in chronic heart failure. In this study, the potential inhibitory effect of peroxisome proliferator-activated receptor-alpha (PPARalpha) activator fenofibrate on monocyte adhesion in chronic heart failure patients was investigated in vitro. ... Isolated peripheral blood mononuclear cells were collected from 36 patients (aged 65 +/- 8 years) with symptomatic chronic heart failure and from 12 healthy control subjects. The cultured human aortic endothelial cells were stimulated with or without 2 ng mL(-1) tumor necrosis factor-alpha (TNF-alpha) and the inhibitory effects of fenofibrate at 25, 50, 100 and 200 uM on endothelial mononuclear cell adhesion were tested. Furthermore, the human aortic endothelial cells were stimulated with 70% sera obtained from chronic heart failure patients and control individuals, respectively, with or without pretreatments with fenofibrate. The endothelial expression of vascular cell adhesion molecule-1 (VCAM-1) and intercellular adhesion molecule-1 (ICAM-1) was then confirmed by mRNA expression and Western blot. ... The increased adhesion of peripheral blood mononuclear cells to TNF-alpha-stimulated human aortic endothelial cells in chronic heart failure patients was reduced when the human aortic endothelial cells were pretreated with fenofibrate (31% inhibition, P = 0.0121). However, pretreatment of the isolated peripheral blood mononuclear cells collected from chronic heart failure patients with fenofibrate failed to suppress their adherence to TNF-alpha-stimulated human aortic endothelial cells. Furthermore, stimulation of cultured human aortic endothelial cells with chronic heart failure patient sera significantly increased VCAM-1 and ICAM-1 expression, which could also be inhibited by fenofibrate. The fenofibrate directly inhibits monocyte binding by TNF-alpha-activated human aortic endothelial cells, probably through preventing up-regulation of cell adhesion molecules by endothelial cells in response to inflammatory stimuli. This PPARalpha activator may have the potential to ameliorate vascular inflammation in patients with chronic heart failure.

PMID:19531154 Huang WP et al; Eur J Clin Invest. 2009 Jun 15. (Epub ahead of print)


4.3 Drug Warning

Severe rashes requiring hospitalization and corticosteroid therapy, including Stevens-Johnson syndrome and toxic epidermal necrolysis, have been reported rarely with fenofibrate in clinical studies. Urticaria and rash also have been reported in approximately 1% of patients receiving fenofibrate therapy in controlled trials.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1732


Fenofibrate, like other fibric acid derivatives (e.g., gemfibrozil), may increase cholesterol excretion in bile, resulting in cholelithiasis. If gallbladder studies indicate the presence of gallstones, fenofibrate should be discontinued.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1732


Liver function tests should be performed periodically (i.e., every 3 months) during the first 12 months of therapy. If serum aminotransferase concentrations of 3 times the upper limit of normal or higher persist, fenofibrate therapy should be discontinued.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1732


Chronic active hepatitis and cholestatic hepatitis have occurred as early as several weeks and as late as several years after initiation of fenofibrate therapy; cirrhosis associated with chronic active hepatitis has been reported rarely with fenofibrate.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1732


For more Drug Warnings (Complete) data for Fenofibrate (17 total), please visit the HSDB record page.


4.4 Drug Indication

Fenofibrate is indicated as adjunctive therapy to diet to reduce elevated LDL-C, Total-C, Triglycerides, and Apo B, and to increase HDL-C adults with primary hypercholesterolemia or mixed dyslipidemia. Fenofibrate is also indicated to treat adults with severe hypertriglyceridemia.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Fenofibrate is a fibrate that activates peroxisome proliferator activated receptor alpha (PPAR) to alter lipid metabolism and treat primary hypercholesterolemia, mixed dyslipidemia, and severe hypertriglyceridemia. Fenofibrate requires once daily dosing and has a half life of 19-27 hours so its duration of action is long. Fenofibrate capsules are given at a dose of 50-150mg daily so the therapeutic index is wide. Patients should be counselled about the risk of rhabdomyolysis, myopathy, and cholelithiasis when taking fibrates.


5.2 MeSH Pharmacological Classification

Hypolipidemic Agents

Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS. (See all compounds classified as Hypolipidemic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FENOFIBRATE
5.3.2 FDA UNII
U202363UOS
5.3.3 Pharmacological Classes
Peroxisome Proliferator Receptor alpha Agonist [EPC]
5.4 ATC Code

C10AB05

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


C10AB05

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448


C - Cardiovascular system

C10 - Lipid modifying agents

C10A - Lipid modifying agents, plain

C10AB - Fibrates

C10AB05 - Fenofibrate


5.5 Absorption, Distribution and Excretion

Absorption

A single 300mg oral dose of fenofibrate reaches a Cmax of 6-9.5mg/L with a Tmax of 4-6h in healthy, fasting volunteers.


Route of Elimination

5-25% of a dose of fenofibrate is eliminated in the feces, while 60-88% is eliminated in the urine. 70-75% of the dose recovered in the urine is in the form of fenofibryl glucuronide and 16% as fenofibric acid.


Volume of Distribution

The volume of distribution of fenofibrate is 0.89L/kg, and can be as high as 60L.


Clearance

The oral clearance of fenofibrate is 1.1L/h in young adults and 1.2L/h in the elderly.


Upon multiple dosing of fenofibrate, fenofibric acid steady state is achieved within 9 days. Plasma concentrations of fenofibric acid at steady state are approximately double those following a single dose. Serum protein binding was approximately 99% in normal and hyperlipidemic subjects.

Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 521


The absolute bioavailability of fenofibrate cannot be determined as the compound is virtually insoluble in aqueous media suitable for injection. However, fenofibrate is well absorbed from the gastrointestinal tract. Following oral administration in healthy volunteers, approximately 60% of a single dose of radiolabelled fenofibrate appeared in urine, primarily as fenofibric acid and its glucuronate conjugate, and 25% was excreted in the feces. Peak plasma levels of fenofibric acid occur within 6 to 8 hours after administration.

Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 520


After absorption, fenofibrate is mainly excreted in the urine in the form of metabolites, primarily fenofibric acid and fenofibric acid glucuronide. After administration of radiolabelled fenofibrate, approximately 60% of the dose appeared in the urine and 25% was excreted in the feces.

Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 521


The metabolism and disposition of orally administered single doses of (14)C fenofibrate (isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2- methylpropionate) have been studied in rat, guinea pig, and dog. In rats, the urinary excretion of (14)C in 5 days varied from 11 to 51% of the dose and was markedly dependent upon the dose form given. The interpretation of these data in terms of factors affecting the absorption of fenofibrate from the gut is complicated by the enterohepatic recirculation of metabolites. The tissue distribution of (14)C after oral administration of an ethanolic solution of fenofibrate has been studied in the rat. The only tissues in which the concentration of (14)C exceeded that in the blood were the organs of absorption and elimination, the gut, liver, and kidneys. Guinea pigs excreted 53% of the dose in the urine in 5 days, with a further 34% in the feces, while in dogs the corresponding figures were 9% and 81%, respectively. In all three species, all the urinary metabolites were products of ester hydrolysis, and the principal excretion product was "reduced fenofibric acid" which arose by subsequent carbonyl reduction. Glucuronidation of fenofibric acid and "reduced fenofibric acid" was a very minor reaction in the rat and guinea pig and was not detected in the dog. In addition, polar unknown metabolite(s) were detected in all three species, but were not investigated further. The results are discussed in terms of the comparative disposition of fenofibrate and other hypolipidemic agents and the contribution of these findings to the safety assessment of such drugs.

PMID:2898351 Weil A et al; Drug Metab Dispos 16 (2): 302-9 (1988).


5.6 Metabolism/Metabolites

Fenofibrate is completely hydrolyzed by liver carboxylesterase 1 to fenofibric acid. Fenofibric acid is either glucuronidated or has its carbonyl group reduced to a benzhydrol that is then glucuronidated. Glucuronidation of fenofibrate metabolites is mediated by UGT1A9. Reduction of the carbonyl group is primarily mediated by CBR1 and minorly by AKR1C1, AKR1C2, AKR1C3, and AKR1B1.


... The metabolism of fenofibrate was investigated in cynomolgus monkeys by ultraperformance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOFMS)-based metabolomics. Urine samples were collected before and after oral doses of fenofibrate. The samples were analyzed in both positive-ion and negative-ion modes by UPLC-QTOFMS, and after data deconvolution, the resulting data matrices were subjected to multivariate data analysis. Pattern recognition was performed on the retention time, mass/charge ratio, and other metabolite-related variables. Synthesized or purchased authentic compounds were used for metabolite identification and structure elucidation by liquid chromatography tandem mass spectrometry. Several metabolites were identified, including fenofibric acid, reduced fenofibric acid, fenofibric acid ester glucuronide, reduced fenofibric acid ester glucuronide, and compound X. Another two metabolites (compound B and compound AR), not previously reported in other species, were characterized in cynomolgus monkeys. More importantly, previously unknown metabolites, fenofibric acid taurine conjugate and reduced fenofibric acid taurine conjugate were identified, revealing a previously unrecognized conjugation pathway for fenofibrate.

PMID:19251819 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2683687 Liu A et al; Drug Metab Dispos 37 (6): 1157-63 (2009).


Fenofibrate has been widely used for the treatment of dyslipidemia with a long history. Species differences of its metabolism were reported, but its metabolites in rodent have not been fully investigated. Urine and plasma samples were collected before and after oral dosages of fenofibrate in Sprague-Dawley rats. Urine samples were subjected to ultra-performance liquid chromatography-electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-ESI-QTOF-MS) analysis, and projection to latent structures discriminant analysis was used for the identification of metabolites. New metabolites in urine and plasma were also studied by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The metabolism pathway was studied in rat hepatocytes. Synthesized and purchased authentic compounds were used for metabolite identification by LC-MS/MS. Five ever-reported metabolites were identified and another four new ones were found. Among these new metabolites, fenofibric acid taurine and reduced fenofibric acid taurine indicate new phase II conjugation pathway of fenofibrate.

PMID:19350456 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2794380 Liu A et al; Xenobiotica 39 (4): 345-54 (2009).


Following oral administration, fenofibrate is rapidly hydrolyzed by esterases to the active metabolite, fenofibric acid; no unchanged fenofibrate is detected in plasma. Fenofibric acid is primarily conjugated with glucuronic acid and then excreted in urine. A small amount of fenofibric acid is reduced at the carbonyl moiety to a benzhydrol metabolite which is, in turn, conjugated with glucuronic acid and excreted in urine. In vivo metabolism data indicate that neither fenofibrate nor fenofibric acid undergo oxidative metabolism (e.g., cytochrome P450) to a significant extent.

Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 521


The metabolism and disposition of orally administered single doses of (14)C fenofibrate (isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2- methylpropionate) have been studied in rat, guinea pig, and dog. In rats, the urinary excretion of (14)C in 5 days varied from 11 to 51% of the dose and was markedly dependent upon the dose form given. The interpretation of these data in terms of factors affecting the absorption of fenofibrate from the gut is complicated by the enterohepatic recirculation of metabolites. The tissue distribution of (14)C after oral administration of an ethanolic solution of fenofibrate has been studied in the rat. The only tissues in which the concentration of (14)C exceeded that in the blood were the organs of absorption and elimination, the gut, liver, and kidneys. Guinea pigs excreted 53% of the dose in the urine in 5 days, with a further 34% in the feces, while in dogs the corresponding figures were 9% and 81%, respectively. In all three species, all the urinary metabolites were products of ester hydrolysis, and the principal excretion product was "reduced fenofibric acid" which arose by subsequent carbonyl reduction. Glucuronidation of fenofibric acid and "reduced fenofibric acid" was a very minor reaction in the rat and guinea pig and was not detected in the dog. In addition, polar unknown metabolite(s) were detected in all three species, but were not investigated further. The results are discussed in terms of the comparative disposition of fenofibrate and other hypolipidemic agents and the contribution of these findings to the safety assessment of such drugs.

PMID:2898351 Weil A et al; Drug Metab Dispos 16 (2): 302-9 (1988).


5.7 Biological Half-Life

Fenofibric acid, the active metabolite of fenofibrate, has a half life of 23 hours. Fenofibrate has a half life of 19-27 hours in healthy subjects and up to 143 hours in patients with renal failure.


Fenofibric acid is eliminated with a half-life of 20 hours, allowing once daily administration in a clinical setting. /Fenofibric acid/

Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 521


5.8 Mechanism of Action

Fenofibrate activates peroxisome proliferator activated receptor alpha (PPAR), increasing lipolysis, activating lipoprotein lipase, and reducing apoprotein C-III. PPAR is a nuclear receptor and its activation alters lipid, glucose, and amino acid homeostasis. Activation of PPAR activates transcription of gene transcription and translation that generates peroxisomes filled with hydrogen peroxide, reactive oxygen species, and hydroxyl radicals that also participate in lipolysis. This mechanism of increased lipid metabolism is also associated with increased oxidative stress on the liver. In rare cases this stress can lead to cirrhosis and chronic active hepatitis.


Fenofibrate is a synthetic ligand for the nuclear receptor peroxisome proliferator-activated receptor (PPAR) alpha and has been widely used in the treatment of metabolic disorders, especially hyperlipemia, due to its lipid-lowering effect. The molecular mechanism of lipid-lowering is relatively well defined: an activated PPARalpha forms a PPAR-RXR heterodimer and this regulates the transcription of genes involved in energy metabolism by binding to PPAR response elements in their promoter regions, so-called "trans-activation". In addition, fenofibrate also has anti-inflammatory and anti-athrogenic effects in vascular endothelial and smooth muscle cells. /There is/ limited information about the anti-inflammatory mechanism of fenofibrate; however, "trans-repression" which suppresses production of inflammatory cytokines and adhesion molecules probably contributes to this mechanism. Furthermore, there are reports that fenofibrate affects endothelial cells in a PPARalpha-independent manner. In order to identify PPARalpha-dependently and PPARalpha-independently regulated transcripts, ... microarray data from human endothelial cells treated with fenofibrate, and with and without siRNA-mediated knock-down of PPARalpha /were obtained/. ... Dynamic Bayesian transcriptome networks /were used/ to reveal PPARalpha-dependent and -independent pathways. Transcriptome network analysis identified growth differentiation factor 15 (GDF15) as a hub gene having PPARalpha-independently regulated transcripts as its direct downstream children. This result suggests that GDF15 may be PPARalpha-independent master-regulator of fenofibrate action in human endothelial cells.

PMID:19357976 Araki H et al; Angiogenesis 12 (3): 221-9 ( 2009).


The effects of fenofibric acid seen in clinical practice have been explained in vivo in transgenic mice and in vitro in human hepatocyte cultures by the activation of peroxisome proliferator activated receptor a (PPARa). Through this mechanism, fenofibrate increases lipolysis and elimination of triglyceride-rich particles from plasma by activating lipoprotein lipase and reducing production of apoprotein C-III (an inhibitor of lipoprotein lipase activity). The resulting fall in triglycerides produces an alteration in the size and composition of LDL from small, dense particles (which are thought to be atherogenic due to their susceptibility to oxidation), to large buoyant particles. These larger particles have a greater affinity for cholesterol receptors and are catabolized rapidly. Activation of PPARa also induces an increase in the synthesis of apoproteins A-I, A-II and HDL-cholesterol.

Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 520


... /This study/ investigated whether fenofibrate affects serum levels of retinol-binding protein-4 (RBP4), an adipocytokine that has recently been shown to link obesity and insulin resistance. Fenofibrate treatment significantly decreased serum RBP4 levels of dyslipidemic patients, which correlated with reduced body weight and increased insulin sensitivity. ... the effect of fenofibrate on RBP4 expression in obese rats /were also examined/. Fenofibrate greatly decreased RBP4 mRNA levels in adipose tissue but not in the liver, which correlated with decreased serum RBP4 levels and increased insulin sensitivity in obese rats. Consistent with a direct effect on RBP4 expression, fenofibrate treatment significantly reduced the mRNA expression levels of RPB4 in 3T3-L1 adipocytes. ...

PMID:19088257 Wu H et al; Am J Physiol Endocrinol Metab 296 (4): E628-34 (2009).


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04-Jan-2021
29-Oct-2024
KGS
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Average Price (USD/KGS)

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

API Imports and Exports

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 160MG

USFDA APPLICATION NUMBER - 21350

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DOSAGE - CAPSULE;ORAL - 150MG

USFDA APPLICATION NUMBER - 21612

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DOSAGE - CAPSULE;ORAL - 50MG

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DOSAGE - TABLET;ORAL - 145MG

USFDA APPLICATION NUMBER - 21656

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DOSAGE - TABLET;ORAL - 48MG

USFDA APPLICATION NUMBER - 21656

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DOSAGE - CAPSULE;ORAL - 130MG

USFDA APPLICATION NUMBER - 21695

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DOSAGE - CAPSULE;ORAL - 30MG **Federal Regist...DOSAGE - CAPSULE;ORAL - 30MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21695

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DOSAGE - CAPSULE;ORAL - 43MG

USFDA APPLICATION NUMBER - 21695

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DOSAGE - CAPSULE;ORAL - 90MG

USFDA APPLICATION NUMBER - 21695

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DOSAGE - TABLET;ORAL - 105MG

USFDA APPLICATION NUMBER - 22418

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DOSAGE - TABLET;ORAL - 35MG

USFDA APPLICATION NUMBER - 22418

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