Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H21ClO4 |
Molecular Weight | 360.831 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C2=CC=C(Cl)C=C2
InChI
InChIKey=YMTINGFKWWXKFG-UHFFFAOYSA-N
InChI=1S/C20H21ClO4/c1-13(2)24-19(23)20(3,4)25-17-11-7-15(8-12-17)18(22)14-5-9-16(21)10-6-14/h5-13H,1-4H3
Molecular Formula | C20H21ClO4 |
Molecular Weight | 360.831 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25903954
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25903954
Fenofibrate is a drug of the fibrate class. It is mainly used to reduce cholesterol levels in people at risk of cardiovascular disease. It’s used as adjunctive therapy to diet to reduce elevated LDL-C, Total-C,Triglycerides and Apo B, and to increase HDL-C in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb). Fenofibrate is a fibric acid derivative, a prodrug comprising fenofibric acid linked to an isopropyl ester. Fenofibrate is rapidly hydrolyzed after oral ingestion to its pharmacologically active form, fenofibric acid. The effects of fenofibric acid seen in clinical practice have been explained in vivo in transgenic mice and in vitro in human hepatocyte cultures by the activation of peroxisome proliferator activated receptor α (PPARα). It lowers lipid levels by activating peroxisome proliferator-activated receptor alpha (PPARα). PPARα activates lipoprotein lipase and reduces apoprotein CIII (an inhibitor of lipoprotein lipase activity), which increases lipolysis and elimination of triglyceride-rich particles from plasma. The resulting fall in triglycerides produces an alteration in the size and composition of LDL from small, dense particles (which are thought to be atherogenic due to their susceptibility to oxidation), to large buoyant particles. These larger particles have a greater affinity for cholesterol receptors and are catabolized rapidly. PPARα also increases apoproteins AI and AII, reduces VLDL- and LDL-containing apoprotein B, and increases HDL-containing apoprotein AI and AII.Fenofibrate also reduces serum uric acid levels in hyperuricemic and normal individuals by increasing the urinary excretion of uric acid. Fenofibrate also has an off-label use as uricosuric therapy in people who have gout.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25903954
Curator's Comment: fenofbrate cannot cross the blood-brain barrier and reach the central nervous system
Originator
Curator's Comment: Procetofen was synthesized in 1974 and was introduced in clinical practice in France the same year. Procetofen, which significantly decreased plasma lipid concentrations in hyperlipidemic patients, was later called fenofibrate to comply with World Health Organization nomenclature guidelines
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26693220 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | TRICOR Approved UseTreatment of Hypercholesterolemia. TRICOR is indicated as adjunctive therapy to diet to reduce elevated LDL-C, Total-C, Triglycerides
and Apo B, and to increase HDL-C in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb). lipid-altering agents should be used in addition to a diet restricted in saturated fat and cholesterol when response to diet and non-pharmacological interventions alone has been inadequate (see National Cholesterol Education Program [NCEP] Treatment
Treatment of Hypertriglyceridemia: TRICOR is also indicated as adjunctive therapy to diet for treatment of adult patients with
hypertriglyceridemia (Fredrickson Types IV and V hyperlipidemia). Improving glycemic control in diabetic patients showing fasting chylomicronemia will usually reduce fasting triglycerides and eliminate chylomicronemia thereby obviating the need for pharmacologic intervention. Launch Date1.09952644E12 |
|||
Palliative | TRICOR Approved UseTreatment of Hypercholesterolemia. TRICOR is indicated as adjunctive therapy to diet to reduce elevated LDL-C, Total-C, Triglycerides
and Apo B, and to increase HDL-C in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb). lipid-altering agents should be used in addition to a diet restricted in saturated fat and cholesterol when response to diet and non-pharmacological interventions alone has been inadequate (see National Cholesterol Education Program [NCEP] Treatment
Treatment of Hypertriglyceridemia: TRICOR is also indicated as adjunctive therapy to diet for treatment of adult patients with
hypertriglyceridemia (Fredrickson Types IV and V hyperlipidemia). Improving glycemic control in diabetic patients showing fasting chylomicronemia will usually reduce fasting triglycerides and eliminate chylomicronemia thereby obviating the need for pharmacologic intervention. Launch Date1.09952644E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.96 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27648957 |
67 mg single, oral dose: 67 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOFIBRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
51.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27648957 |
67 mg single, oral dose: 67 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOFIBRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27648957 |
67 mg single, oral dose: 67 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOFIBRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16 h |
160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FENOFIBRIC ACID serum | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FENOFIBRIC ACID serum | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Other AEs: Asthenia, Pain... Other AEs: Asthenia (1.1%) Sources: Pain (1.1%) Headache (3.4%) Migraine (2.3%) Dyspepsia (2.3%) Gastrointestinal disorder (1.1%) Nausea (3.4%) Diarrhoea (1.1%) Myalgia (1.1%) Dizziness (1.1%) Abnormal thinking (1.1%) |
145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Other AEs: Abdominal pain, Back pain... Other AEs: Abdominal pain (4.6%) Sources: Back pain (3.4%) Headache (3.2%) Nausea (2.3%) Constipation (2.1%) Abnormal liver function tests (7.5%) ALT increased (3%) CPK increased (3%) AST increased (3.4%) Respiratory disorder (6.2%) Rhinitis (2.3%) Urticaria (1.1%) Rash (1.4%) |
200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy n = 46 Health Status: unhealthy Condition: hyperlipoproteinaemia Sex: M+F Population Size: 46 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abnormal thinking | 1.1% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Asthenia | 1.1% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Diarrhoea | 1.1% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Dizziness | 1.1% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Gastrointestinal disorder | 1.1% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Myalgia | 1.1% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Pain | 1.1% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Dyspepsia | 2.3% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Migraine | 2.3% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Headache | 3.4% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Nausea | 3.4% | 200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 49.5 n = 87 Health Status: unhealthy Condition: dyslipidemia Age Group: 49.5 Sex: M+F Population Size: 87 Sources: |
Urticaria | 1.1% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Rash | 1.4% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Constipation | 2.1% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Nausea | 2.3% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Rhinitis | 2.3% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
ALT increased | 3% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
CPK increased | 3% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Headache | 3.2% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
AST increased | 3.4% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Back pain | 3.4% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Abdominal pain | 4.6% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Respiratory disorder | 6.2% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Abnormal liver function tests | 7.5% | 145 mg 1 times / day multiple, oral Recommended Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: |
unhealthy, adult n = 439 Health Status: unhealthy Condition: dyslipidemia Age Group: adult Population Size: 439 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 3.0 |
moderate | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
weak | |||
Page: 3.0 |
weak | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/26700956/ Page: 16.0 |
yes [IC50 170 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/ Page: 6.0 |
yes [IC50 2.39 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/14698041/ Page: 4.0 |
yes [IC50 5.83 uM] | |||
yes [Inhibition 50 uM] | ||||
yes [Ki 105.2 uM] | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/14698041/ Page: 1.0 |
no | |||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/15304429/ Page: 3.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Expression of peroxisomal proliferator-activated receptors and retinoid X receptors in the kidney. | 1999 Dec |
|
Fibrates suppress fibrinogen gene expression in rodents via activation of the peroxisome proliferator-activated receptor-alpha. | 1999 May 1 |
|
Fenofibrate and rosiglitazone lower serum triglycerides with opposing effects on body weight. | 2000 May 10 |
|
Treating lipid abnormalities in patients with type 2 diabetes mellitus. | 2001 Dec 20 |
|
Benefits of micronised Fenofibrate in type 2 diabetes mellitus subjects with good glycemic control. | 2001 Feb 1 |
|
Peroxisome proliferator-activated receptor alpha is not rate-limiting for the lipoprotein-lowering action of fish oil. | 2001 Feb 16 |
|
Apoprotein c-III and E-containing lipoparticles are markedly increased in HIV-infected patients treated with protease inhibitors: association with the development of lipodystrophy. | 2001 Jan |
|
Deterioration in renal function associated with fibrate therapy. | 2001 Jan |
|
Fenofibrate and warfarin interaction. | 2001 Jul |
|
Fibrate induction of the adrenoleukodystrophy-related gene (ABCD2): promoter analysis and role of the peroxisome proliferator-activated receptor PPARalpha. | 2001 Jun |
|
Role of fibrates and HMG-CoA reductase inhibitors in gallstone formation: epidemiological study in an unselected population. | 2001 Mar |
|
Choice of lipid-regulating drugs. | 2001 May 28 |
|
Comparison of DNA damage photoinduced by ketoprofen, fenofibric acid and benzophenone via electron and energy transfer. | 2001 Nov |
|
Effects of fenofibrate and gemfibrozil on plasma homocysteine. | 2001 Nov 24 |
|
Effects of fenofibrate on lipid parameters in obese rhesus monkeys. | 2001 Oct |
|
[Effect of phenofibrate treatment on endothelial dysfunction in patients with history of myocardial infarction in young age]. | 2002 |
|
Pancreatitis associated with simvastatin plus fenofibrate. | 2002 Feb |
|
A laser flash photolysis study of fenofibric acid in aqueous buffered media: unexpected triplet state inversion in a derivative of 4-alkoxybenzophenone. | 2002 Mar |
Sample Use Guides
Primary Hypercholesterolemia or Mixed Hyperlipidemia: the initial dose of TRICOR (FENOFIBRATE TABLETS) is 145 mg per day
Hypertriglyceridemia: the initial dose is 48 to 145 mg per day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27629528
Fenofibrate may protect against endothelin-1 (ET-1)-induced cardiomyocyte hypertrophy and enhanced adiponectin expression through modulation of PPARα expression in vitro and limitation of daunorubicin cardiotoxicity in vivo, suggesting a novel mechanistic insight into the role of PPARα and adiponectin in cardiachypertrophy and heart failure.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:32:23 UTC 2023
by
admin
on
Wed Jul 05 22:32:23 UTC 2023
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Record UNII |
U202363UOS
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175375
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WHO-VATC |
QC10BA03
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WHO-ATC |
C10BA04
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LIVERTOX |
NBK548607
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NCI_THESAURUS |
C98150
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WHO-VATC |
QC10AB05
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WHO-ATC |
C10BA03
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WHO-ATC |
C10AB05
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WHO-VATC |
QC10BA04
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NDF-RT |
N0000170118
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NDF-RT |
N0000175596
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N0000170118
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C29047
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49562-28-9
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CHEMBL672
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221100
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U202363UOS
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256-376-3
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5001
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Fenofibrate
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1269447
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D011345
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8703
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FENOFIBRATE
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M5279
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DTXSID2029874
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3339
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100000092530
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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
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