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Details

Stereochemistry ACHIRAL
Molecular Formula C15H22O3
Molecular Weight 250.3334
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEMFIBROZIL

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)

HIDE SMILES / InChI

Molecular Formula C15H22O3
Molecular Weight 250.3334
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
A risk factor for atherosclerosis: triglyceride-rich lipoproteins.
2001
Hypercholesterolemia, lipid-lowering agents, and the risk for brain infarction.
2001
Hypertriglyceridemia: a review of clinical relevance and treatment options: focus on cerivastatin.
2001
Severe rhabdomyolysis associated with the cerivastin-gemfibrozil combination therapy: report of a case.
2001
[Rhabdomyolysis complicated with acute renal insufficiency in a patient treated with gemfibrozil and cerivastatin].
2001 Apr
Rhabdomyolysis and acute renal failure following a switchover of therapy between two fibric acid derivatives.
2001 Aug
[Fatal rhabdomyolysis caused by cerivastatin].
2001 Aug
Inhibitory action of gemfibrozil on cholesterol absorption in rat intestine.
2001 Aug
Gemfibrozil treatment potentiates oxidative resistance of high-density lipoprotein in hypertriglyceridemic patients.
2001 Aug
A sensitive method for the determination of gemfibrozil in human plasma samples by RP-LC.
2001 Aug
Bayer decides to withdraw cholesterol lowering drug.
2001 Aug 18
Baycol withdrawn from market.
2001 Aug 21
Altered expression of the carboxylesterases ES-4 and ES-10 by peroxisome proliferator chemicals.
2001 Aug 28
[Lipid-lowering drugs].
2001 Dec
Massive rhabdomyolysis and life threatening hyperkalaemia in a patient with the combination of cerivastatin and gemfibrozil.
2001 Dec
Treatment for the procoagulant state in type 2 diabetes.
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
Targeting low high-density lipoprotein cholesterol for therapy: lessons from the Veterans Affairs High-density Lipoprotein Intervention Trial.
2001 Dec 20
Gemfibrozil prevents major coronary events by increasing HDL-cholesterol and more.
2001 Jul
Fenofibrate and warfarin interaction.
2001 Jul
The effects of lipid-lowering agents on acute renal allograft rejection.
2001 Jul 27
Effects of fenofibrate and gemfibrozil on plasma homocysteine.
2001 Jul 7
Normocholesterolaemic dysslipidaemia: is there a role for fibrates?
2001 Jun 4
Normocholesterolaemic dyslipidaemia: is there a role for fibrates?
2001 Jun 4
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
PPARS, metabolic disease and atherosclerosis.
2001 Nov
Clinical inquiries. What laboratory monitoring is appropriate to detect adverse drug reactions in patients on cholesterol-lowering agents?
2001 Nov
Niacin, but not gemfibrozil, selectively increases LP-AI, a cardioprotective subfraction of HDL, in patients with low HDL cholesterol.
2001 Nov
Gemfibrozil increases paraoxonase activity in type 2 diabetic patients. A new hypothesis of the beneficial action of fibrates?
2001 Nov
Gemfibrozil is a potent inhibitor of human cytochrome P450 2C9.
2001 Nov
Effects of fenofibrate and gemfibrozil on plasma homocysteine.
2001 Nov 24
Effects of fenofibrate and gemfibrozil on plasma homocysteine.
2001 Nov 24
Statin-associated myopathy.
2001 Nov 5
Fatal rhabdomyolysis caused by lipid-lowering therapy.
2001 Oct
Serum magnesium status during lipid-lowering drug treatment in non-insulin-dependent diabetic patients.
2001 Oct
Cyclic nucleotides in platelets of genetically hypertriglyceridemic and hypertensive rats. Thrombin and nitric oxide responses are unrelated to plasma triglyceride levels.
2001 Oct 1
[Cerivastatin and gemfibrozil: a dangerous combination].
2001 Oct 15
Molecular basis for the effect of lipid lowering drugs on growth factors after de-endothelialization.
2001 Sep
[Cholestatic hepatitis caused by gemfibrozil].
2001 Sep
Cerivastatin and gemfibrozil-associated rhabdomyolysis.
2001 Sep
Is the relationship between adipose tissue and waist girth altered by weight loss in obese men?
2001 Sep
Increase in hepatic expression of SREBP-2 by gemfibrozil administration to rats.
2001 Sep 15
Bayer pulls cerivastatin (Baycol) from market.
2001 Sep 4
[Rhabdomyolysis and anuric kidney failure induced by the treatment with a gemfibrozil-cerivastatin combination].
2001 Sep-Oct
Therapy and clinical trials.
2002 Feb
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
Patents

Sample Use Guides

In Vivo Use Guide
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
Sustained potent reduction of [Ca²⁺]i in cultured rat VSMCs was observed with Gemfibrozil 50mg/L
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:48:28 UTC 2019
Edited
by admin
on Mon Oct 21 20:48:28 UTC 2019
Record UNII
Q8X02027X3
Record Status Validated (UNII)
Record Version
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Name Type Language
GEMFIBROZIL
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
GEMFIBROZIL [IARC]
Common Name English
GEMFIBROZIL [HSDB]
Common Name English
2,2-DIMETHYL-5-(2,5-XYLYLOXY) VALERIC ACID
Systematic Name English
GEMFIBROZIL [INN]
Common Name English
GEMFIBROZIL [EP]
Common Name English
GEMFIBROZIL [MART.]
Common Name English
GEMFIBROZIL [USAN]
Common Name English
GEMFIBROZIL [USP-RS]
Common Name English
GEMFIBROZIL [JAN]
Common Name English
GEMFIBROZIL [ORANGE BOOK]
Common Name English
GEMFIBROZIL [WHO-DD]
Common Name English
GEMFIBROZIL [USP]
Common Name English
GEMFIBROZIL [MI]
Common Name English
CI-719
Code English
PENTANOIC ACID, 5-(2,5-DIMETHYLPHENOXY)-2,2-DIMETHYL-
Common Name English
LOPID
Brand Name English
GEMFIBROZIL [VANDF]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/18/1993
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
NCI_THESAURUS C98150
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
WHO-VATC QC10AB04
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
FDA ORPHAN DRUG 591917
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
FDA ORPHAN DRUG 546216
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
NDF-RT N0000170118
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
NDF-RT N0000175375
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
NDF-RT N0000175596
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
WHO-ATC C10AB04
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
NDF-RT N0000170118
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
LIVERTOX 452
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
Code System Code Type Description
CAS
25812-30-0
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
LactMed
25812-30-0
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
HSDB
25812-30-0
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
DRUG BANK
DB01241
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
ECHA (EC/EINECS)
247-280-2
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
INN
3899
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
EPA CompTox
25812-30-0
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
EVMPD
SUB07894MIG
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
IUPHAR
3439
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
RXCUI
4719
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY RxNorm
MESH
D015248
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
NCI_THESAURUS
C29071
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
MERCK INDEX
M5692
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL457
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
WIKIPEDIA
GEMFIBROZIL
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
PUBCHEM
3463
Created by admin on Mon Oct 21 20:48:28 UTC 2019 , Edited by admin on Mon Oct 21 20:48:28 UTC 2019
PRIMARY
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