CHOLINE FENOFIBRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H14ClO4.C5H14NO
Molecular Weight	421.914
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(C)CCO.CC(C)(OC1=CC=C(C=C1)C(=O)C2=CC=C(Cl)C=C2)C([O-])=O

InChI

InChIKey=JWAZHODZSADEHB-UHFFFAOYSA-M

InChI=1S/C17H15ClO4.C5H14NO/c1-17(2,16(20)21)22-14-9-5-12(6-10-14)15(19)11-3-7-13(18)8-4-11;1-6(2,3)4-5-7/h3-10H,1-2H3,(H,20,21);7H,4-5H2,1-3H3/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C5H13NO
Molecular Weight	103.1628
Charge	0
Count

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

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


Effect of colesevelam HCl on single-dose fenofibrate pharmacokinetics.	2004	15509187
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 new fenofibrate formulation: results of six single-dose, clinical studies of bioavailability under fed and fasting conditions.	2004 Sep	15531008
Simvastatin does not have a clinically significant pharmacokinetic interaction with fenofibrate in humans.	2004 Sep	15317833
Fenofibrate, troglitazone, and 15-deoxy-Delta12,14-prostaglandin J2 close KATP channels and induce insulin secretion.	2004 Sep	15201343
Fenofibric acid.	2005 Feb	15695917
Impaired expression of the peroxisome proliferator-activated receptor alpha during hepatitis C virus infection.	2005 Feb	15685545
Comparative effects of fibrates on drug metabolizing enzymes in human hepatocytes.	2005 Jan	15771232
Troglitazone and 15-deoxy-delta(12,14)-prostaglandin J2 inhibit shear-induced coupling factor 6 release in endothelial cells.	2005 Jul 1	15949477
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
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
Regulation of adiponectin receptor 1 in human hepatocytes by agonists of nuclear receptors.	2005 Sep 2	16023994
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
Activating effect of benzbromarone, a uricosuric drug, on peroxisome proliferator-activated receptors.	2007	18274627
LC-MS analysis and environmental risk of lipid regulators.	2007 Feb	17047939
Update on the clinical utility of fenofibrate in mixed dyslipidemias: mechanisms of action and rational prescribing.	2008	19183747
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
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
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
Regulation of sulfotransferase and UDP-glucuronosyltransferase gene expression by the PPARs.	2009	19680455
MBX-102/JNJ39659100, a novel non-TZD selective partial PPAR-γ agonist lowers triglyceride independently of PPAR-α activation.	2009	19404482
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
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
Fenofibric Acid (trilipix).	2009 May 4	19417718
Selective modulation of amyloid-beta peptide degradation by flurbiprofen, fenofibrate, and related compounds regulates Abeta levels.	2009 Nov	19702658
In vitro glucuronidation of fenofibric acid by human UDP-glucuronosyltransferases and liver microsomes.	2009 Nov	19661212
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
Probing the fibrate binding specificity of rat liver fatty acid binding protein.	2009 Sep 10	19663428
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 `Thu Jul 06 21:52:49 UTC 2023` Edited by `admin` on `Thu Jul 06 21:52:49 UTC 2023`
Record UNII	4BMH7IZT98
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHOLINE FENOFIBRATE

Official Name

English

ABT-335

Code

English

Choline fenofibrate [WHO-DD]

Common Name

English

FENOFIBRIC ACID CHOLINE SALT

Common Name

English

FENOFIBRIC ACID CHOLINE SALT [MI]

Common Name

English

CHOLINE FENOFIBRATE [USP-RS]

Common Name

English

CHOLINE FENOFIBRATE [USAN]

Common Name

English

choline fenofibrate [INN]

Common Name

English

CHOLINE FENOFIBRATE [MART.]

Common Name

English

TRILIPIX

Brand Name

English

ETHANAMINIUM, 2-HYDROXY-N,N,N-TRIMETHYL-, SALT WITH 2-(4-(4- CHLOROBENZOYL)PHENOXY)-2-METHYLPROPANOIC ACID (1:1)

Common Name

English

CHOLINE FENOFIBRATE [ORANGE BOOK]

Common Name

English

2-HYDROXY-N,N,N-TRIMETHYLETHANAMINIUM 2-(4-(4-CHLOROBENZOYL)PHENOXY)-2- METHYLPROPANOATE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QC10AB11