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Also known as: 42017-89-0, Procetofenic acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic acid, Trilipix, Nsc 281318
Molecular Formula
C17H15ClO4
Molecular Weight
318.7  g/mol
InChI Key
MQOBSOSZFYZQOK-UHFFFAOYSA-N
FDA UNII
BGF9MN2HU1

CAS 42017-89-0
Fenofibric Acid is the active form of fenofibrate, a synthetic phenoxy-isobutyric acid derivate with antihyperlipidemic activity.
Fenofibric acid is a Peroxisome Proliferator Receptor alpha Agonist.
1 2D Structure

CAS 42017-89-0

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic acid
2.1.2 InChI
InChI=1S/C17H15ClO4/c1-17(2,16(20)21)22-14-9-5-12(6-10-14)15(19)11-3-7-13(18)8-4-11/h3-10H,1-2H3,(H,20,21)
2.1.3 InChI Key
MQOBSOSZFYZQOK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)(C(=O)O)OC1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)Cl
2.2 Other Identifiers
2.2.1 UNII
BGF9MN2HU1
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 42017-89-0

2. Procetofenic Acid

3. 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic Acid

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

5. Trilipix

6. Nsc 281318

7. Fnf Acid

8. Lf 153

9. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic Acid

10. Fenofibrate Related Compound B

11. Bgf9mn2hu1

12. Chembl981

13. Nsc-281318

14. Propanoic Acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-

15. Chebi:83469

16. Fibricor

17. Lf-153

18. Mfcd00792461

19. Fenofibric Acid-d6

20. 2-{4-[(4-chlorophenyl)carbonyl]phenoxy}-2-methylpropanoic Acid

21. 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionic Acid

22. Propanoic Acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-

23. Fenofibricacid

24. Alpha 1081

25. 2-[4-(4-chlorobenzene-1-carbonyl)phenoxy]-2-methylpropanoic Acid

26. Lf 178 Acid

27. Abt 335

28. Ccris 7302

29. Einecs 255-626-9

30. Unii-bgf9mn2hu1

31. Brn 2058973

32. Fenofibric-acid

33. Feno-fibric Acid

34. Fibricor (tn)

35. F5a

36. Fenofibrate Free Acid

37. Fenofibric Acid

38. Schembl16377

39. Gtpl2662

40. Zinc1984

41. Fenofibric Acid [vandf]

42. Dtxsid8041030

43. Bdbm28700

44. Fenofibric Acid [usp-rs]

45. Fenofibric Acid [who-dd]

46. Fenofibrate Free Acid [mi]

47. Amy25229

48. Bcp22437

49. Hy-b0760

50. Fenofibric Acid, Analytical Standard

51. Nsc281318

52. S4527

53. Fenofibric Acid [orange Book]

54. Akos015889489

55. Ccg-213311

56. Db13873

57. Ks-1234

58. Ac-22277

59. Sy052754

60. F1011

61. Ft-0600402

62. D11579

63. D83849

64. Fenofibrate Related Compound B [usp-rs]

65. Fenofibric Acid 100 Microg/ml In Acetonitrile

66. Ab01563028_01

67. 017f890

68. A825720

69. W-106287

70. 2-[4-(p-chlorobenzoyl)phenoxy]-2-methylpropionicacid

71. Q27077290

72. 2-[4-(4-chlorobenzoyl)-phenoxy]-2-methylpropionic Acid

73. 2-[4-(4-chloro-benzoyl)-phenoxy]-2-methyl-propionic Acid

74. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic Acid, 95%

75. 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic Acid (fenofibric Acid)

76. Fenofibrate Impurity B, European Pharmacopoeia (ep) Reference Standard

77. Fenofibrate Related Compound B, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 318.7 g/mol
Molecular Formula C17H15ClO4
XLogP33.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass318.0658866 g/mol
Monoisotopic Mass318.0658866 g/mol
Topological Polar Surface Area63.6 Ų
Heavy Atom Count22
Formal Charge0
Complexity405
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 3  
Drug NameFENOFIBRIC ACID
Active IngredientCHOLINE FENOFIBRATE
CompanyACTAVIS ELIZABETH (Application Number: A200920); ALEMBIC PHARMS LTD (Application Number: A208705); ANCHEN PHARMS (Application Number: A201573); IMPAX LABS INC (Application Number: A200264); LUPIN LTD (Application Number: A200750); MYLAN PHARMS INC (Application Number: A200913)

2 of 3  
Drug NameTRILIPIX
Active IngredientCHOLINE FENOFIBRATE
CompanyABBVIE (Application Number: N022224. Patent: 7259186)

3 of 3  
Drug NameFIBRICOR
Active IngredientFENOFIBRIC ACID
CompanyARALEZ PHARMS INC (Application Number: N022418. Patents: 7569612, 7741373, 7741374, 7915247)

4.2 Drug Indication

For use as an adjunctive therapy to diet to: (a) reduce triglyceride levels in adult patients with severe hypertriglyceridemia, and (b) reduce elevated total cholesterol, low-density-lipoprotein (LDL-C), triglycerides, and apolipoprotein B, and to increase high-density-lipoprotein (HDL-C) in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb).


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Various clinical studies have shown that elevated levels of total cholesterol, low-desnsity-lipoprotein (LDL-C), and apolipoprotein B (apo B) - an LDL membrane complex - are associated with human atherosclerosis. Concurrently, decreased levels of high-density-lioprotein (HDL-C) and its transport complex, apolipoproteins apo AI and apo AII, are associated with the development of atherosclerosis. Furthermore, epidemiological investigations demonstrate that cardiovascular morbidity and mortality vary directly with the levels of total cholesterol, LDL-C, and triglycerides, and inversely with the level of HDL-C. Fenofibric acid, the active metabolite of fenofibrate, subsequently produces reductions in total cholesterol, LDL-C, apo B, total triglycerides, and triglyceride rich lipoprotein (VLDL) in treated patients. Moreover, such treatment with fenofibrate also results in increases in HDL-C and apo AI and apo AII.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
FENOFIBRIC ACID
5.2.2 FDA UNII
BGF9MN2HU1
5.2.3 Pharmacological Classes
Peroxisome Proliferator Receptor alpha Agonist [EPC]
5.3 ATC Code

C10AB05

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


5.4 Absorption, Distribution and Excretion

Absorption

Some studies have demonstrated that the bioavailability of fenofibric acid (a sample administration of 130 mg oral suspension to healthy volunteers about 4 hours after a light breakfast) is approximately 81% in the stomach, 88% in the proximal small bowel, 84% in the distal small bowel, and 78% in the colon. Nevertheless, following the oral administration of fenofibric acid in healthy volunteers, median peak plasma levels for the drug occurred about 2.5 hours after administration. Moreover, exposure after administration of three 35 mg fenofibric acid tablets is largely comparable to that of one 105 mg tablet.


Route of Elimination

Fenofibric acid metabolites are largely excreted in the urine.


Volume of Distribution

The volume of distribution for fenofibric acid is demonstrated to be 70.9 +/- 27.5 L.


Clearance

In five elderly volunteers aged 77 to 87, the oral clearance of fenofibric acid after a single oral dose of fenofibrate was 1.2 L/h, which compares to 1.1 L/h in young adults.


5.5 Metabolism/Metabolites

In vitro and in vivo metabolism studies reveal that fenofibric acid does not experience significant oxidative metabolism via the cytochrome P450 isoenzymes. The CYP1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 enzymes are not known to play a role in the metabolism of fenofibric acid. Rather, fenofibric acid is predominantly conjugated with glucuronic acid and then excreted in urine. A small amount of fenofibric acid is reduced at the carbonyl moiety to benzhydrol metabolite which is, in turn, conjugated with glucuronic acid and excreted in urine.


Fenofibric Acid has known human metabolites that include Fenofibryl glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

Following once daily dosing, fenofibric acid demonstrates an elimination associated with a half-life of about 20 hours after absorption.


5.7 Mechanism of Action

Having performed clinical studies with in vivo transgenic mice and in vitro human hepatocyte cultures, it is believed that the principal mechanism of action of fenofibric acid is demonstrated through its capability to activate peroxisome proliferator receptor alpha (PPAR-alpha). By activating PPAR-alpha, fenofibric acid increases lipolysis and the elimination of triglyceride-rich particles from plasma by actuating lipoprotein lipase and reducing production of apoprotein C-III, which acts as an inhibitor of lipoprotein lipase activity. The resultant decrease in triglycerides causes an alteration in the size and composition of low-density-lipoprotein from small, dense particles to large, buoyant ones. The size of these larger low-density-lipoprotein particles have a greater affinity for cholesterol receptors and are therefore catabolized more rapidly. Additionally, fenofibric acid's activation of PPAR-alpha also induces an increase in the synthesis of apoproteins apo A-I, apo A-II, and high-density-lipoprotein. Moreover, the use of fenofibric acid can also act to reduce serum uric acid levels in ordinary or hyperuricemic individuals by increasing the urinary excretion of uric acid.


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