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	C17H15ClO4
Molecular Weight	318.752
Charge	0
Count

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

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

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
Drug treatment of combined hyperlipidemia.	2001	14728015
A potent PPARalpha agonist stimulates mitochondrial fatty acid beta-oxidation in liver and skeletal muscle.	2001 Feb	11158930
PPARalpha agonists inhibit tissue factor expression in human monocytes and macrophages.	2001 Jan 16	11208678
Statin-induced inhibition of the Rho-signaling pathway activates PPARalpha and induces HDL apoA-I.	2001 Jun	11390424
Choice of lipid-regulating drugs.	2001 May 28	11378632
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
A laser flash photolysis study of fenofibric acid in aqueous buffered media: unexpected triplet state inversion in a derivative of 4-alkoxybenzophenone.	2002 Mar	11950084
Induction of plasminogen activator inhibitor-1 in endothelial cells by basic fibroblast growth factor and its modulation by fibric acid.	2002 May 1	12006402
Update on fenofibrate.	2002 Winter	12481201
An open-label, randomized, three-way crossover trial of the effects of coadministration of rosuvastatin and fenofibrate on the pharmacokinetic properties of rosuvastatin and fenofibric acid in healthy male volunteers.	2003 Feb	12749507
A chemical switch regulates fibrate specificity for peroxisome proliferator-activated receptor alpha (PPARalpha ) versus liver X receptor.	2003 Jan 24	12441342
Simvastatin does not have a clinically significant pharmacokinetic interaction with fenofibrate in humans.	2004 Sep	15317833
Optimal lipid modification: the rationale for combination therapy.	2005	17315604
Comparative effects of fibrates on drug metabolizing enzymes in human hepatocytes.	2005 Jan	15771232
Fenofibrate: a novel formulation (Triglide) in the treatment of lipid disorders: a review.	2006	17722529
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
Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid.	2007 Aug	17470524
Update on the clinical utility of fenofibrate in mixed dyslipidemias: mechanisms of action and rational prescribing.	2008	19183747
Nanocrystal technology, drug delivery and clinical applications.	2008	18990939
A novel PPARalpha agonist ameliorates insulin resistance in dogs fed a high-fat diet.	2008 May	18212024
Fenofibrate set to benefit from new research on its active metabolite, fenofibric acid.	2008 May-Jun	18568186
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
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 simvastatin in patients with mixed dyslipidemia: a phase 3, randomized, controlled study.	2009 Jan	19081418
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
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
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 `Sat Dec 16 16:23:09 GMT 2023` Edited by `admin` on `Sat Dec 16 16:23:09 GMT 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