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=C(C)C(OCCCC(C)(C)C(O)=O)=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 Date1981 |
|||
| 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 Date1981 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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: |
|
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 |
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: |
unhealthy, 59 |
Disc. AE: Depression, Flushing... AEs leading to discontinuation/dose reduction: Depression (1.1%) Sources: Flushing (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: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
Disc. AE: Abdominal cramps, Abnormal liver function tests... AEs leading to discontinuation/dose reduction: Abdominal cramps Sources: Abnormal 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: |
unhealthy, 59 |
| 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: |
unhealthy, 59 |
| 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: |
unhealthy, 59 |
| 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: |
unhealthy, 59 |
| 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: |
unhealthy, 59 |
| Abdominal cramps | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
| Abnormal liver function tests | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
| CPK increased | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
| Diarrhea | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
| Joint pain | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
| Muscle pain | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
| Nausea | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
| Vomiting | Disc. AE | 9 g single, oral Overdose Dose: 9 g Route: oral Route: single Dose: 9 g Sources: |
healthy, 7 Health Status: healthy Age Group: 7 Sources: |
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 |
|---|---|---|
| Therapy and clinical trials. | 2002-02 |
|
| 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. | 2002-01-28 |
|
| [Rhabdomyolysis and anuric kidney failure induced by the treatment with a gemfibrozil-cerivastatin combination]. | 2002-01-25 |
|
| Sexual dysfunction secondary to gemfibrozil. | 2002-01 |
|
| Targeting low high-density lipoprotein cholesterol for therapy: lessons from the Veterans Affairs High-density Lipoprotein Intervention Trial. | 2001-12-20 |
|
| Determination of drugs in surface water and wastewater samples by liquid chromatography-mass spectrometry: methods and preliminary results including toxicity studies with Vibrio fischeri. | 2001-12-14 |
|
| [Lipid-lowering drugs]. | 2001-12 |
|
| Massive rhabdomyolysis and life threatening hyperkalaemia in a patient with the combination of cerivastatin and gemfibrozil. | 2001-12 |
|
| Treatment for the procoagulant state in type 2 diabetes. | 2001-12 |
|
| Rhabdomyolysis with HMG CoA reductase inhibitors: a class effect? | 2001-12 |
|
| Effects of fenofibrate and gemfibrozil on plasma homocysteine. | 2001-11-24 |
|
| Effects of fenofibrate and gemfibrozil on plasma homocysteine. | 2001-11-24 |
|
| Statin-associated myopathy. | 2001-11-05 |
|
| Attenuation by fibrates of plasminogen activator inhibitor type-1 expression in human arterial smooth muscle cells. | 2001-11 |
|
| 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. | 2001-11 |
|
| Effect of gemfibrozil on the pharmacokinetics and pharmacodynamics of glimepiride. | 2001-11 |
|
| Ciprofibrate versus gemfibrozil in the treatment of mixed hyperlipidemias: an open-label, multicenter study. | 2001-11 |
|
| PPARS, metabolic disease and atherosclerosis. | 2001-11 |
|
| Clinical inquiries. What laboratory monitoring is appropriate to detect adverse drug reactions in patients on cholesterol-lowering agents? | 2001-11 |
|
| Niacin, but not gemfibrozil, selectively increases LP-AI, a cardioprotective subfraction of HDL, in patients with low HDL cholesterol. | 2001-11 |
|
| Gemfibrozil increases paraoxonase activity in type 2 diabetic patients. A new hypothesis of the beneficial action of fibrates? | 2001-11 |
|
| Are high density lipoprotein (HDL) and triglyceride levels relevant in stroke prevention? | 2001-11 |
|
| Gemfibrozil is a potent inhibitor of human cytochrome P450 2C9. | 2001-11 |
|
| [Cerivastatin and gemfibrozil: a dangerous combination]. | 2001-10-15 |
|
| Cyclic nucleotides in platelets of genetically hypertriglyceridemic and hypertensive rats. Thrombin and nitric oxide responses are unrelated to plasma triglyceride levels. | 2001-10-01 |
|
| Fatal rhabdomyolysis caused by lipid-lowering therapy. | 2001-10 |
|
| Serum magnesium status during lipid-lowering drug treatment in non-insulin-dependent diabetic patients. | 2001-10 |
|
| [Fibrates in the secondary prevention of ischemic cardiopathy]. | 2001-09-22 |
|
| [Severe rhabdomyolysis associated with cerivastatin and gemfibrozil]. | 2001-09-15 |
|
| Increase in hepatic expression of SREBP-2 by gemfibrozil administration to rats. | 2001-09-15 |
|
| Bayer pulls cerivastatin (Baycol) from market. | 2001-09-04 |
|
| Molecular basis for the effect of lipid lowering drugs on growth factors after de-endothelialization. | 2001-09 |
|
| [Cholestatic hepatitis caused by gemfibrozil]. | 2001-09 |
|
| Cerivastatin and gemfibrozil-associated rhabdomyolysis. | 2001-09 |
|
| Smoking diminishes the beneficial effect of statins: observations from the landmark trials. | 2001-09 |
|
| Is the relationship between adipose tissue and waist girth altered by weight loss in obese men? | 2001-09 |
|
| New developments in the prevention of atherosclerosis in patients with low high-density lipoprotein cholesterol. | 2001-09 |
|
| Altered expression of the carboxylesterases ES-4 and ES-10 by peroxisome proliferator chemicals. | 2001-08-28 |
|
| Baycol withdrawn from market. | 2001-08-21 |
|
| Bayer decides to withdraw cholesterol lowering drug. | 2001-08-18 |
|
| Statin-fibrate combination therapy. | 2001-08-04 |
|
| Rhabdomyolysis and acute renal failure following a switchover of therapy between two fibric acid derivatives. | 2001-08 |
|
| [Fatal rhabdomyolysis caused by cerivastatin]. | 2001-08 |
|
| Inhibitory action of gemfibrozil on cholesterol absorption in rat intestine. | 2001-08 |
|
| Effect of a six month gemfibrozil treatment and dietary recommendations on the metabolic risk profile of visceral obese men. | 2001-08 |
|
| The effects of lipid-lowering agents on acute renal allograft rejection. | 2001-07-27 |
|
| Gemfibrozil prevents major coronary events by increasing HDL-cholesterol and more. | 2001-07 |
|
| [Peroxisome proliferator-activated receptors (PPARs) in the vessel wall: new regulators of gene expression in vascular cells]. | 2001-07 |
|
| A risk factor for atherosclerosis: triglyceride-rich lipoproteins. | 2001 |
|
| Hypercholesterolemia, lipid-lowering agents, and the risk for brain infarction. | 2001 |
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
Mon Mar 31 17:54:17 GMT 2025
by
admin
on
Mon Mar 31 17:54:17 GMT 2025
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| Record UNII |
Q8X02027X3
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| Record Status |
Validated (UNII)
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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
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| Code System | Code | Type | Description | ||
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25812-30-0
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7735
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DB01241
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Q8X02027X3
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247-280-2
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3899
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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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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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CHEMBL457
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GEMFIBROZIL
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5296
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3463
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> INHIBITOR |
MAJOR
IC50
|
||
|
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 | |||
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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
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
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 |
|---|---|---|---|---|---|---|
| Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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