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 61 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17343371	Agonist 2637		4500.0 nM [EC50]
Fatty acid binding protein intestinal 2 Target ID: CHEMBL4879 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18533710	Inhibitor 8146		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 8307	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 1670 inducer 753 inhibitor 1532	substrate 985 inducer 372 inhibitor 1695	substrate 1168 inducer 97 inhibitor 1789

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 770 CYP2C8 869 CYP2E1 846 CYP1A2 1463 P-gp 1401 OATP1B1 770 CYP2C19 1410 CYP2A6 670 OAT3 625	CYP1A2 1013 CYP2A6 510 CYP2B6 648 CYP2C8 670 CYP2C19 955 CYP2E1 633 UGT1A3 421 UGT1A6 306 UGT1A9 378 UGT2B7 387	CYP1A2 671 CYP2A6 79 CYP2B6 521 CYP2C19 283 CYP2E1 121 CYP2C8 163 UGT1A1 66

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C9 1747	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	moderate
CYP1A2 1620	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP1A2 1620	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP2A6 702	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2B6 946	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C19 1484	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C8 923	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2C9 1747	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2D6 1826	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2D6 1826	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP2E1 929	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP2E1 929	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
CYP3A4 1857	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	no
CYP3A4 1857	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=7 Page: 7.0	no
P-gp 1588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/14698041/	no
CYP2A6 702	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	weak
CYP2C19 1484	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021350s005lbl.pdf; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2922314/	weak
UGT1A1 249	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/15771232/	weak
OAT3 627	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/17314201/	yes [IC50 2.2 uM]
OATP1B1 785	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/16316932/	yes [IC50 20 uM]
CYP2C8 923	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022418s000_ClinPharmR.pdf#page=11 Page: 11.0	yes [IC50 282 uM]
CYP2B6 946	inhibitor 3185 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 387	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	major
UGT1A3 421	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
UGT1A6 306	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
UGT1A9 378	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774983/	minor
CYP1A2 1013	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2A6 510	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2B6 648	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C19 955	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C8 670	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2C9 985	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2D6 1168	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP2E1 633	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022418lbl.pdf#page=6 Page: 6.0	no
CYP3A4 1670	substrate 3264 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

Statin-induced inhibition of the Rho-signaling pathway activates PPARalpha and induces HDL apoA-I.	2001 Jun	11390424
PPARalpha and PPARdelta activators inhibit cytokine-induced nuclear translocation of NF-kappaB and expression of VCAM-1 in EAhy926 endothelial cells.	2002 Jan 25	11821020
Induction of plasminogen activator inhibitor-1 in endothelial cells by basic fibroblast growth factor and its modulation by fibric acid.	2002 May 1	12006402
Dilazep and fenofibric acid inhibit MCP-1 mRNA expression in glycoxidized LDL-stimulated human endothelial cells.	2003 Aug 15	12954370
Identification of hepatic transcriptional changes in insulin-resistant rats treated with peroxisome proliferator activated receptor-alpha agonists.	2003 Jun	12790802
Influence of lipid lowering fibrates on P-glycoprotein activity in vitro.	2004 Jan 15	14698041
Fenofibrate and fenofibric acid analysis by capillary electrophoresis.	2004 Jun	15188253
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
Gene expression profiling of potential peroxisome proliferator-activated receptor (PPAR) target genes in human hepatoblastoma cell lines inducibly expressing different PPAR isoforms.	2005 Oct 3	16197558
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
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
Rapid broad-spectrum analgesia through activation of peroxisome proliferator-activated receptor-alpha.	2006 Dec	16997973
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
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
Cryptochrome and Period Proteins Are Regulated by the CLOCK/BMAL1 Gene: Crosstalk between the PPARs/RXRalpha-Regulated and CLOCK/BMAL1-Regulated Systems.	2008	18317514
PPARalpha regulates the hepatotoxic biomarker alanine aminotransferase (ALT1) gene expression in human hepatocytes.	2008 Aug 15	18455211
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
Treatment of hyperlipidaemia with fenofibrate and related fibrates.	2008 Oct	18808320
Advances in the medical treatment of diabetic retinopathy.	2009 Aug	19638526
Capecitabine-induced severe hypertriglyceridaemia and diabetes: a case report and review of the literature.	2009 Dec	20002489
Differentiated CaCo-2 cells as an in-vitro model to evaluate de-novo apolipoprotein A-I production in the small intestine.	2009 Jun	19445040
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
Selective modulation of amyloid-beta peptide degradation by flurbiprofen, fenofibrate, and related compounds regulates Abeta levels.	2009 Nov	19702658
Determination of fenofibric acid in human plasma by ultra performance liquid chromatography-electrospray ionization mass spectrometry: application to a bioequivalence study.	2009 Sep	19353730

Substance Class	Chemical Created by `admin` on `Fri Dec 16 20:29:48 UTC 2022` Edited by `admin` on `Fri Dec 16 20:29:48 UTC 2022`
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