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 2678		4500.0 nM [EC50]
Fatty acid binding protein intestinal 2 Target ID: CHEMBL4879 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18533710	Inhibitor 8297		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 8429	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 2009

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 1737 inducer 781 inhibitor 1587	substrate 1037 inducer 389 inhibitor 1767	substrate 1217 inducer 97 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 810 CYP2C8 911 CYP2E1 882 CYP1A2 1524 P-gp 1461 OATP1B1 788 CYP2C19 1478 CYP2A6 707 OAT3 642	CYP1A2 1054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C19 991 CYP2E1 667 UGT1A3 422 UGT1A6 307 UGT1A9 380 UGT2B7 389	CYP1A2 701 CYP2A6 79 CYP2B6 547 CYP2C19 293 CYP2E1 128 CYP2C8 168 UGT1A1 69

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	moderate
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP2A6 739	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C19 1553	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C8 965	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C9 1819	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2D6 1891	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP2E1 970	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14698041/	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	weak
CYP2C19 1553	inhibitor 3277 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 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15771232/	weak
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17314201/	yes [IC50 2.2 uM]
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16316932/	yes [IC50 20 uM]
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	yes [IC50 282 uM]
CYP2B6 1001	inhibitor 3277 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 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	major
UGT1A3 422	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
UGT1A6 307	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
UGT1A9 380	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2A6 543	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2B6 664	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C8 693	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2E1 667	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP3A4 1737	substrate 3367 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
Comparison of DNA damage photoinduced by ketoprofen, fenofibric acid and benzophenone via electron and energy transfer.	2001 Nov	11723794
Effect of fenofibrate on plasma concentration and urinary excretion of purine bases and oxypurinol.	2001 Oct	11669172
Regulation of lipid metabolism and gene expression by fenofibrate in hamsters.	2001 Oct 31	11731332
Peroxisome proliferator-activated receptor alpha induces hepatic expression of the human bile acid glucuronidating UDP-glucuronosyltransferase 2B4 enzyme.	2003 Aug 29	12810707
Photosensitization of thymine nucleobase by benzophenone derivatives as models for photoinduced DNA damage: Paterno-Büchi vs energy and electron transfer processes.	2004 Jul	15257609
A novel selective peroxisome proliferator-activated receptor alpha agonist, 2-methyl-c-5-[4-[5-methyl-2-(4-methylphenyl)-4-oxazolyl]butyl]-1,3-dioxane-r-2-carboxylic acid (NS-220), potently decreases plasma triglyceride and glucose levels and modifies lipoprotein profiles in KK-Ay mice.	2004 Jun	14982965
Fenofibrate, troglitazone, and 15-deoxy-Delta12,14-prostaglandin J2 close KATP channels and induce insulin secretion.	2004 Sep	15201343
Fenofibric acid.	2005 Feb	15695917
Comparative effects of fibrates on drug metabolizing enzymes in human hepatocytes.	2005 Jan	15771232
Effects of fibrates on human organic anion-transporting polypeptide 1B1-, multidrug resistance protein 2- and P-glycoprotein-mediated transport.	2005 Jul	16316932
Bezafibrate increases very-long-chain acyl-CoA dehydrogenase protein and mRNA expression in deficient fibroblasts and is a potential therapy for fatty acid oxidation disorders.	2005 Sep 15	16115821
Regulation of adiponectin receptor 1 in human hepatocytes by agonists of nuclear receptors.	2005 Sep 2	16023994
Absence of a food effect with a 145 mg nanoparticle fenofibrate tablet formulation.	2006 Feb	16502765
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
Activating effect of benzbromarone, a uricosuric drug, on peroxisome proliferator-activated receptors.	2007	18274627
Influence of HDL-cholesterol-elevating drugs on the in vitro activity of the HDL receptor SR-BI.	2007 Aug	17533223
LC-MS analysis and environmental risk of lipid regulators.	2007 Feb	17047939
Effects of peroxisome proliferator-activated receptor activation on gonadotropin transcription and cell mitosis induced by bone morphogenetic proteins in mouse gonadotrope LbetaT2 cells.	2007 Jul	17592024
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
Update on the clinical utility of fenofibrate in mixed dyslipidemias: mechanisms of action and rational prescribing.	2008	19183747
Statins Activate Human PPARalpha Promoter and Increase PPARalpha mRNA Expression and Activation in HepG2 Cells.	2008	19125197
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
PPARalpha regulates the hepatotoxic biomarker alanine aminotransferase (ALT1) gene expression in human hepatocytes.	2008 Aug 15	18455211
Characterization of the drug binding specificity of rat liver fatty acid binding protein.	2008 Jul 10	18533710
Fenofibrate set to benefit from new research on its active metabolite, fenofibric acid.	2008 May-Jun	18568186
Treatment of hyperlipidaemia with fenofibrate and related fibrates.	2008 Oct	18808320
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
Fenofibrate-loaded PLGA microparticles: effects on ischemic stroke.	2009 Apr 11	19168134
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
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
IVIVC in oral absorption for fenofibrate immediate release tablets using a dissolution/permeation system.	2009 Jun	18855916
Efficacy and safety of ABT-335 (fenofibric acid) in combination with rosuvastatin in patients with mixed dyslipidemia: a phase 3 study.	2009 May	18996523
Fenofibric Acid (trilipix).	2009 May 4	19417718
Myopathy with statin-fibrate combination therapy: clinical considerations.	2009 Sep	19636324
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:33:38 GMT 2023` Edited by `admin` on `Fri Dec 15 16:33:38 GMT 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