FENOFIBRIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H15ClO4
Molecular Weight	318.752
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(OC1=CC=C(C=C1)C(=O)C2=CC=C(Cl)C=C2)C(O)=O

InChI

InChIKey=MQOBSOSZFYZQOK-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C17H15ClO4
Molecular Weight	318.752
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17343371	Agonist 2662		4500.0 nM [EC50]
Fatty acid binding protein intestinal 2 Target ID: CHEMBL4879 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18533710	Inhibitor 8228		1000.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
hypertriglyceridemia 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022418s011lbl.pdf	Primary		Approved 8360	FIBRICOR Approved Use FIBRICOR is a peroxisome proliferator receptor alpha (PPARα) activator indicated as an adjunct to diet: to reduce triglyceride (TG) levels in adult patients with severe hypertriglyceridemia (> 500 mg/dL); to reduce elevated total cholesterol (TC), low-density-lipoprotein cholesterol (LDL-C), TG and apolipoprotein (Apo) B and to increase high-density lipoprotein cholesterol (HDL-C) in adult patients with primary hypercholesterolemia or mixed dyslipidemia. Launch Date 1.25020799E12

C_max

Value	Dose	Co-administered	Analyte	Population
8.37 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf	105 mg 1 times / day steady-state, oral dose: 105 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		FENOFIBRIC ACID unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
12 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf	105 mg 1 times / day steady-state, oral dose: 105 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		FENOFIBRIC ACID unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
124 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf	105 mg 1 times / day steady-state, oral dose: 105 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		FENOFIBRIC ACID unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
162.96 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf	105 mg 1 times / day steady-state, oral dose: 105 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		FENOFIBRIC ACID unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf	105 mg 1 times / day steady-state, oral dose: 105 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		FENOFIBRIC ACID unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
135 mg 1 times / day multiple, oral Recommended Dose: 135 mg, 1 times / day Route: oral Route: multiple Dose: 135 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022224s003lbl.pdf	unhealthy, adult n = 490 Health Status: unhealthy Age Group: adult Population Size: 490 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022224s003lbl.pdf	Other AEs: Constipation, Diarrhea... Other AEs: Constipation (3.3%) Diarrhea (3.9%) Dyspepsia (3.7%) Nausea (4.3%) Fatigue (2%) Pain (3.5%) Nasopharyngitis (3.5%) Sinusitis (3.3%) Upper respiratory tract infection (5.3%) ALT increased (1.2%) Arthralgia (3.9%) Back pain (6.3%) Muscle spasms (1.6%) Myalgia (3.3%) Pain in extremity (4.5%) Dizziness (4.1%) Headache (12.7%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022224s003lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709 inducer 768 inhibitor 1579	substrate 1010 inducer 383 inhibitor 1752	substrate 1193 inducer 97 inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 799 CYP2C8 901 CYP2E1 876 CYP1A2 1509 P-gp 1437 OATP1B1 781 CYP2C19 1463 CYP2A6 704 OAT3 636	CYP1A2 1032 CYP2A6 523 CYP2B6 660 CYP2C8 688 CYP2C19 985 CYP2E1 648 UGT1A3 422 UGT1A6 307 UGT1A9 380 UGT2B7 389	CYP1A2 689 CYP2A6 79 CYP2B6 538 CYP2C19 290 CYP2E1 126 CYP2C8 168 UGT1A1 69

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	moderate
CYP1A2 1673	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP2A6 736	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2B6 985	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C19 1537	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C8 955	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C9 1803	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2D6 1875	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP2E1 964	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP3A4 1909	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
P-gp 1626	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/14698041/	no
CYP2A6 736	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	weak
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	weak
UGT1A1 254	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/15771232/	weak
OAT3 638	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/17314201/	yes [IC50 2.2 uM]
OATP1B1 796	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/16316932/	yes [IC50 20 uM]
CYP2C8 955	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	yes [IC50 282 uM]
CYP2B6 985	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	yes [IC50 741 uM]	weak (co-administration study) Comment: IC50 value from pre-incubation study; Coadministration with efavirenz (CYP2B6 substrate) resulted in AUC decrease of efavirenz by 12% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0

Drug as victim

Target	Modality	Activity
UGT2B7 389	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	major
UGT1A3 422	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
UGT1A6 307	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
UGT1A9 380	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
CYP1A2 1032	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2A6 523	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2B6 660	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C19 985	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C8 688	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C9 1010	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2E1 648	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP3A4 1709	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:83469	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:83469
ChemicalBook	CB8400259	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8400259
MolPort	MolPort-000-002-475	https://www.molport.com/shop/molecule-link/MolPort-000-002-475
ZINC	ZINC000000001984	http://zinc15.docking.org/substances/ZINC000000001984
eMolecules	591140	https://www.emolecules.com/cgi-bin/more?vid=591140

PubMed

Title	Date	PubMed
A new fenofibrate formulation: results of six single-dose, clinical studies of bioavailability under fed and fasting conditions.	2004 Sep	15531008
Optimal lipid modification: the rationale for combination therapy.	2005	17315604
Fenofibric acid.	2005 Feb	15695917
Impaired expression of the peroxisome proliferator-activated receptor alpha during hepatitis C virus infection.	2005 Feb	15685545
Effects of fibrates on human organic anion-transporting polypeptide 1B1-, multidrug resistance protein 2- and P-glycoprotein-mediated transport.	2005 Jul	16316932
Fenofibric acid, an active form of fenofibrate, increases apolipoprotein A-I-mediated high-density lipoprotein biogenesis by enhancing transcription of ATP-binding cassette transporter A1 gene in a liver X receptor-dependent manner.	2005 Jun	15790930
Simultaneous determination of rosuvastatin and fenofibric acid in human plasma by LC-MS/MS with electrospray ionization: assay development, validation and application to a clinical study.	2005 Sep 15	15970417
The effects of food on the bioavailability of fenofibrate administered orally in healthy volunteers via sustained-release capsule.	2006	16584288
Absence of a food effect with a 145 mg nanoparticle fenofibrate tablet formulation.	2006 Feb	16502765
Effects of fenofibrate on C-reactive protein levels in hypertriglyceridemic patients.	2006 Jun	16810076
Evaluation of the potential for pharmacokinetic interaction between fenofibrate and ezetimibe: A phase I, open-label, multiple-dose, three-period crossover study in healthy subjects.	2006 Mar	16750452
The PPAR-alpha activator fenofibrate fails to provide myocardial protection in ischemia and reperfusion in pigs.	2006 May	16339839
Aldehyde oxidase 1 is highly abundant in hepatic steatosis and is downregulated by adiponectin and fenofibric acid in hepatocytes in vitro.	2006 Nov 24	17022944
The transfer of a LC-UV method for the determination of fenofibrate and fenofibric acid in Lidoses: use of total error as decision criterion.	2006 Sep 11	16483737
Determination of fenofibric acid concentrations by HPLC after anion exchange solid-phase extraction from human serum.	2007 Apr	17417074
Influence of HDL-cholesterol-elevating drugs on the in vitro activity of the HDL receptor SR-BI.	2007 Aug	17533223
Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid.	2007 Aug	17470524
LC-MS analysis and environmental risk of lipid regulators.	2007 Feb	17047939
Transport of the dipeptidyl peptidase-4 inhibitor sitagliptin by human organic anion transporter 3, organic anion transporting polypeptide 4C1, and multidrug resistance P-glycoprotein.	2007 May	17314201
Statins Activate Human PPARalpha Promoter and Increase PPARalpha mRNA Expression and Activation in HepG2 Cells.	2008	19125197
Nanocrystal technology, drug delivery and clinical applications.	2008	18990939
Evaluation of a new formulation of fenofibric acid, ABT-335, co-administered with statins : study design and rationale of a phase III clinical programme.	2008	18783301
Cryptochrome and Period Proteins Are Regulated by the CLOCK/BMAL1 Gene: Crosstalk between the PPARs/RXRalpha-Regulated and CLOCK/BMAL1-Regulated Systems.	2008	18317514
Dual mechanisms for the fibrate-mediated repression of proprotein convertase subtilisin/kexin type 9.	2008 Apr 11	18245819
Inhibiting wild-type and C299S mutant AKR1B10; a homologue of aldose reductase upregulated in cancers.	2008 Apr 28	18325492
Characterization of the drug binding specificity of rat liver fatty acid binding protein.	2008 Jul 10	18533710
A novel PPARalpha agonist ameliorates insulin resistance in dogs fed a high-fat diet.	2008 May	18212024
An automated method for the simultaneous determination of pravastatin, 3-hydroxy isomeric metabolite, pravalactone and fenofibric acid in human plasma by sensitive liquid chromatography combined with diode array and tandem mass spectrometry detection.	2008 May 2	18342321
Fenofibrate set to benefit from new research on its active metabolite, fenofibric acid.	2008 May-Jun	18568186
Fenofibric acid: in combination therapy in the treatment of mixed dyslipidemia.	2009	19929038
Thinking beyond low-density lipoprotein cholesterol: strategies to further reduce cardiovascular risk.	2009	19812691
MBX-102/JNJ39659100, a novel non-TZD selective partial PPAR-γ agonist lowers triglyceride independently of PPAR-α activation.	2009	19404482
Statins and fenofibrate affect skeletal muscle chloride conductance in rats by differently impairing ClC-1 channel regulation and expression.	2009 Apr	19220292
Advances in the medical treatment of diabetic retinopathy.	2009 Aug	19638526
Peroxisome-proliferator-activated receptor-alpha activation protects brain capillary endothelial cells from oxygen-glucose deprivation-induced hyperpermeability in the blood-brain barrier.	2009 Aug	19534718
Capecitabine-induced severe hypertriglyceridaemia and diabetes: a case report and review of the literature.	2009 Dec	20002489
Efficacy and safety of ABT-335 (fenofibric acid) in combination with atorvastatin in patients with mixed dyslipidemia.	2009 Feb 15	19195513
Efficacy and safety of ABT-335 (fenofibric acid) in combination with simvastatin in patients with mixed dyslipidemia: a phase 3, randomized, controlled study.	2009 Jan	19081418
ABT-335, the choline salt of fenofibric acid, does not have a clinically significant pharmacokinetic interaction with rosuvastatin in humans.	2009 Jan	18952910
Differentiated CaCo-2 cells as an in-vitro model to evaluate de-novo apolipoprotein A-I production in the small intestine.	2009 Jun	19445040
Fenofibrate metabolism in the cynomolgus monkey using ultraperformance liquid chromatography-quadrupole time-of-flight mass spectrometry-based metabolomics.	2009 Jun	19251819
Characterization of lipophilic drug binding to rat intestinal fatty acid binding protein.	2009 Jun	19160019
Fenofibric Acid (trilipix).	2009 May 4	19417718
Myopathy with statin-fibrate combination therapy: clinical considerations.	2009 Sep	19636324
Determination of fenofibric acid in human plasma by ultra performance liquid chromatography-electrospray ionization mass spectrometry: application to a bioequivalence study.	2009 Sep	19353730
Medicinal chemistry of drugs used in diabetic cardiomyopathy.	2010	20015035
Year two assessment of fenofibric acid and moderate-dose statin combination: a phase 3, open-label, extension study.	2010	19995098
Ligand-enhanced expression and in-cell assay of human peroxisome proliferator-activated receptor alpha ligand binding domain.	2010 Apr	19782138
Occurrence of emerging pollutants in urban wastewater and their removal through biological treatment followed by ozonation.	2010 Jan	19628245
Ecotoxicity assessment of lipid regulators in water and biologically treated wastewater using three aquatic organisms.	2010 Jan	19333638

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:59:08 UTC 2023` Edited by `admin` on `Wed Jul 05 23:59:08 UTC 2023`
Record UNII	BGF9MN2HU1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENOFIBRIC ACID

Common Name

English

PROCETOFENIC ACID

Common Name

English

FIBRICOR

Brand Name

English

FENOFIBRIC ACID [ORANGE BOOK]

Common Name

English

FENOFIBRATE FREE ACID [MI]

Common Name

English

FENOFIBRATE RELATED COMPOUND B [USP-RS]

Common Name

English

PROPANOIC ACID, 2-(4-(4-CHLOROBENZOYL)PHENOXY)-2-METHYL-

Common Name

English

LF-153

Code

English

FENOFIBRIC ACID [VANDF]

Common Name

English

NSC-281318

Code

English

FENOFIBRATE RELATED COMPOUND B

Common Name

English

FENOFIBRIC ACID [USP-RS]

Common Name

English

Fenofibric acid [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175596