Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H22O3 |
Molecular Weight | 250.3334 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1
InChI
InChIKey=HEMJJKBWTPKOJG-UHFFFAOYSA-N
InChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)
Molecular Formula | C15H22O3 |
Molecular Weight | 250.3334 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB01241Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018422s055lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01241
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018422s055lbl.pdf
Gemfibrozil, a fibric acid antilipemic agent similar to clofibrate, is used to treat hyperlipoproteinemia and as a second-line therapy for type IIb hypercholesterolemia. It acts to reduce triglyceride levels, reduce VLDL levels, reduce LDL levels (moderately), and increase HDL levels (moderately). Gemfibrozil increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. It does so by activating Peroxisome proliferator-activated receptor-alpha (PPARα) 'transcription factor ligand', a receptor that is involved in metabolism of carbohydrates and fats, as well as adipose tissue differentiation. This increase in the synthesis of lipoprotein lipase thereby increases the clearance of triglycerides. Chylomicrons are degraded, VLDLs are converted to LDLs, and LDLs are converted to HDL. This is accompanied by a slight increase in secretion of lipids into the bile and ultimately the intestine. Gemfibrozil also inhibits the synthesis and increases the clearance of apolipoprotein B, a carrier molecule for VLDL. Gemfibrozil is most commonly sold as the brand name, Lopid. Other brand names include Jezil and Gen-Fibro.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22706077
Curator's Comment: gemfibrozil was shown to cross the blood brain barrier in mice
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16316932 |
12.5 µM [Ki] | ||
Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16299161 |
30.0 µM [IC50] | ||
Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16176562 |
30.4 µM [Ki] | ||
Target ID: CHEMBL239 Sources: http://www.drugbank.ca/drugs/DB01241 |
59.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LOPID Approved UseLOPID (gemfibrozil tablets, USP) is indicated as adjunctive therapy to diet for:
1. Treatment of adult patients with very high elevations of serum triglyceride levels (Types IV and V hyperlipidemia) who present a risk of pancreatitis and who do not respond adequately to a determined dietary effort to control them.
2. Reducing the risk of developing coronary heart disease only in Type IIb patients without history of or symptoms of existing coronary heart disease who have had an inadequate response to weight loss, dietary therapy, exercise, and other pharmacologic agents (such as bile acid sequestrants and nicotinic acid, known to reduce LDL- and raise HDL-cholesterol) and who have the following triad of lipid abnormalities: low HDL-cholesterol levels in addition to elevated LDL-cholesterol
and elevated triglycerides Launch Date3.77654411E11 |
|||
Preventing | LOPID Approved UseLOPID (gemfibrozil tablets, USP) is indicated as adjunctive therapy to diet for:
1. Treatment of adult patients with very high elevations of serum triglyceride levels (Types IV and V hyperlipidemia) who present a risk of pancreatitis and who do not respond adequately to a determined dietary effort to control them.
2. Reducing the risk of developing coronary heart disease only in Type IIb patients without history of or symptoms of existing coronary heart disease who have had an inadequate response to weight loss, dietary therapy, exercise, and other pharmacologic agents (such as bile acid sequestrants and nicotinic acid, known to reduce LDL- and raise HDL-cholesterol) and who have the following triad of lipid abnormalities: low HDL-cholesterol levels in addition to elevated LDL-cholesterol
and elevated triglycerides Launch Date3.77654411E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
28 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19648824 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
GEMFIBROZIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
17400 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01736254 |
600 mg single, oral dose: 600 mg route of administration: oral experiment type: single co-administered: |
GEMFIBROZIL plasma | Homo sapiens population: healthy age: sex: food status: |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
104 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19648824 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
GEMFIBROZIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19648824 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
GEMFIBROZIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 2 times / day multiple, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: Page: p.198 |
unhealthy, 59 n = 87 Health Status: unhealthy Condition: Non-insulin-dependent diabetes mellitus Age Group: 59 Sex: M+F Population Size: 87 Sources: Page: p.198 |
Disc. AE: Depression, Flushing... AEs leading to discontinuation/dose reduction: Depression (1.1%) Sources: Page: p.198Flushing (1.1%) Nausea (2.2%) Vomiting (1.1%) Rash (1.1%) |
9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Disc. AE: Abdominal cramps, Abnormal liver function tests... AEs leading to discontinuation/dose reduction: Abdominal cramps Sources: Page: p.13Abnormal liver function tests Diarrhea CPK increased Joint pain Muscle pain Nausea Vomiting |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Depression | 1.1% Disc. AE |
600 mg 2 times / day multiple, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: Page: p.198 |
unhealthy, 59 n = 87 Health Status: unhealthy Condition: Non-insulin-dependent diabetes mellitus Age Group: 59 Sex: M+F Population Size: 87 Sources: Page: p.198 |
Flushing | 1.1% Disc. AE |
600 mg 2 times / day multiple, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: Page: p.198 |
unhealthy, 59 n = 87 Health Status: unhealthy Condition: Non-insulin-dependent diabetes mellitus Age Group: 59 Sex: M+F Population Size: 87 Sources: Page: p.198 |
Rash | 1.1% Disc. AE |
600 mg 2 times / day multiple, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: Page: p.198 |
unhealthy, 59 n = 87 Health Status: unhealthy Condition: Non-insulin-dependent diabetes mellitus Age Group: 59 Sex: M+F Population Size: 87 Sources: Page: p.198 |
Vomiting | 1.1% Disc. AE |
600 mg 2 times / day multiple, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: Page: p.198 |
unhealthy, 59 n = 87 Health Status: unhealthy Condition: Non-insulin-dependent diabetes mellitus Age Group: 59 Sex: M+F Population Size: 87 Sources: Page: p.198 |
Nausea | 2.2% Disc. AE |
600 mg 2 times / day multiple, oral Recommended Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: Page: p.198 |
unhealthy, 59 n = 87 Health Status: unhealthy Condition: Non-insulin-dependent diabetes mellitus Age Group: 59 Sex: M+F Population Size: 87 Sources: Page: p.198 |
Abdominal cramps | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Abnormal liver function tests | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
CPK increased | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Diarrhea | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Joint pain | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Muscle pain | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Nausea | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Vomiting | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: Page: p.13 |
healthy, 7 n = 1 Health Status: healthy Age Group: 7 Population Size: 1 Sources: Page: p.13 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Ki 1.5 uM] | ||||
yes [Ki 14.2 uM] | ||||
yes [Ki 5.8 uM] | yes (co-administration study) Comment: [PMID:11719730]:Gemfibrozil modestly increases the plasma concentrations of glimepiride. This may be caused by inhibition of CYP2C9. |
|||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | yes (co-administration study) Comment: [PMID:22472994]: CYP2C8 inactivation by gemfibrozil caused dose-dependent increases in AUC of repaglinide |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Rhabdomyolysis and renal failure associated with cerivastatin-gemfibrozil combination therapy. | 1999 Apr 1 |
|
Effects of fibrate compounds on expression of plasminogen activator inhibitor-1 by cultured endothelial cells. | 1999 Jun |
|
Rhabdomyolysis and acute renal failure after changing statin-fibrate combinations. | 2000 |
|
A risk factor for atherosclerosis: triglyceride-rich lipoproteins. | 2001 |
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Hypertriglyceridemia: a review of clinical relevance and treatment options: focus on cerivastatin. | 2001 |
|
Treatment of dyslipoproteinemia in the metabolic syndrome. | 2001 |
|
Effect of a six month gemfibrozil treatment and dietary recommendations on the metabolic risk profile of visceral obese men. | 2001 Aug |
|
Bayer decides to withdraw cholesterol lowering drug. | 2001 Aug 18 |
|
Altered expression of the carboxylesterases ES-4 and ES-10 by peroxisome proliferator chemicals. | 2001 Aug 28 |
|
Treatment for the procoagulant state in type 2 diabetes. | 2001 Dec |
|
Rhabdomyolysis with HMG CoA reductase inhibitors: a class effect? | 2001 Dec |
|
Determination of drugs in surface water and wastewater samples by liquid chromatography-mass spectrometry: methods and preliminary results including toxicity studies with Vibrio fischeri. | 2001 Dec 14 |
|
Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. | 2001 Feb |
|
The effects of gemfibrozil upon the metabolism of chylomicron-like emulsions in patients with endogenous hypertriglyceridemia. | 2001 Feb 1 |
|
Short-term gemfibrozil treatment reverses lipid profile and peroxidation but does not alter blood glucose and tissue antioxidant enzymes in chronically diabetic rats. | 2001 Jan |
|
Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes. | 2001 Jan |
|
Normocholesterolaemic dyslipidaemia: is there a role for fibrates? | 2001 Jan 15 |
|
Gemfibrozil prevents major coronary events by increasing HDL-cholesterol and more. | 2001 Jul |
|
Effect of gemfibrozil on the composition and oxidation properties of very-low-density lipoprotein and high-density lipoprotein in patients with hypertriglyceridemia. | 2001 Jun |
|
Effect of statin versus fibrate on postprandial endothelial dysfunction: role of remnant-like particles. | 2001 Jun |
|
[Helsinki Heart Study]. | 2001 Mar |
|
Relation of gemfibrozil treatment and lipid levels with major coronary events: VA-HIT: a randomized controlled trial. | 2001 Mar 28 |
|
Choice of lipid-regulating drugs. | 2001 May 28 |
|
Attenuation by fibrates of plasminogen activator inhibitor type-1 expression in human arterial smooth muscle cells. | 2001 Nov |
|
Effect of trans-dehydrocrotonin, a 19-nor-clerodane diterpene from Croton cajucara on experimental hypertriglyceridaemia and hypercholesterolaemia induced by Triton WR 1339 (tyloxapol) in mice. | 2001 Nov |
|
Effect of gemfibrozil on the pharmacokinetics and pharmacodynamics of glimepiride. | 2001 Nov |
|
Ciprofibrate versus gemfibrozil in the treatment of mixed hyperlipidemias: an open-label, multicenter study. | 2001 Nov |
|
Clinical inquiries. What laboratory monitoring is appropriate to detect adverse drug reactions in patients on cholesterol-lowering agents? | 2001 Nov |
|
Gemfibrozil increases paraoxonase activity in type 2 diabetic patients. A new hypothesis of the beneficial action of fibrates? | 2001 Nov |
|
Effects of fenofibrate and gemfibrozil on plasma homocysteine. | 2001 Nov 24 |
|
Cyclic nucleotides in platelets of genetically hypertriglyceridemic and hypertensive rats. Thrombin and nitric oxide responses are unrelated to plasma triglyceride levels. | 2001 Oct 1 |
|
[Cholestatic hepatitis caused by gemfibrozil]. | 2001 Sep |
|
Cerivastatin and gemfibrozil-associated rhabdomyolysis. | 2001 Sep |
|
Bayer pulls cerivastatin (Baycol) from market. | 2001 Sep 4 |
|
Sexual dysfunction secondary to gemfibrozil. | 2002 Jan |
|
Cost-effectiveness of gemfibrozil for coronary heart disease patients with low levels of high-density lipoprotein cholesterol: the Department of Veterans Affairs High-Density Lipoprotein Cholesterol Intervention Trial. | 2002 Jan 28 |
Sample Use Guides
The recommended dose for adults is 1200 mg administered in two divided doses 30 minutes before the morning and evening meals
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22285408
Sustained potent reduction of [Ca²⁺]i in cultured rat VSMCs was observed with Gemfibrozil 50mg/L
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:50:46 UTC 2023
by
admin
on
Wed Jul 05 22:50:46 UTC 2023
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Record UNII |
Q8X02027X3
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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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FDA ORPHAN DRUG |
834821
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FDA ORPHAN DRUG |
591917
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EU-Orphan Drug |
EU/3/18/1993
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NCI_THESAURUS |
C98150
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WHO-VATC |
QC10AB04
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FDA ORPHAN DRUG |
591917
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FDA ORPHAN DRUG |
546216
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NDF-RT |
N0000170118
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NDF-RT |
N0000175375
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NDF-RT |
N0000175596
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WHO-ATC |
C10AB04
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NDF-RT |
N0000170118
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LIVERTOX |
NBK547926
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FDA ORPHAN DRUG |
834921
Created by
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Code System | Code | Type | Description | ||
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25812-30-0
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PRIMARY | |||
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7735
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PRIMARY | |||
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DB01241
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PRIMARY | |||
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Q8X02027X3
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247-280-2
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3899
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PRIMARY | |||
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100000092643
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DTXSID0020652
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SUB07894MIG
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Q8X02027X3
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1285
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757024
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3439
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4719
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PRIMARY | RxNorm | ||
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D015248
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1288500
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Gemfibrozil
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C29071
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M5692
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PRIMARY | Merck Index | ||
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CHEMBL457
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PRIMARY | |||
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GEMFIBROZIL
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PRIMARY | |||
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5296
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PRIMARY | |||
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3463
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PRIMARY |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> INHIBITOR |
MAJOR
IC50
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EXCRETED UNCHANGED |
URINE
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TARGET -> ACTIVATOR |
with 100% efficacy
EC50
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
SUBSTRATE USED: ESTRONE-3-SULFATE
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METABOLIC ENZYME -> NON-INHIBITOR | |||
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TARGET -> ACTIVATOR |
with 79% efficacy
EC50
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
|
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IMPURITY -> PARENT |
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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