U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H22O3
Molecular Weight 250.3339
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEMFIBROZIL

SMILES

Cc1ccc(C)c(c1)OCCCC(C)(C)C(=O)O

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

Description
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

Curator's Comment:: gemfibrozil was shown to cross the blood brain barrier in mice

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOPID

Approved Use

LOPID (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 Date

3.77654411E11
Preventing
LOPID

Approved Use

LOPID (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 Date

3.77654411E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
28 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
104 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4.4 h
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

Doses

DosePopulationAdverse 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%)
Flushing (1.1%)
Nausea (2.2%)
Vomiting (1.1%)
Rash (1.1%)
Sources: Page: p.198
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
Abnormal liver function tests
Diarrhea
CPK increased
Joint pain
Muscle pain
Nausea
Vomiting
Sources: Page: p.13
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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
PubMed

PubMed

TitleDatePubMed
A risk factor for atherosclerosis: triglyceride-rich lipoproteins.
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
Treatment of dyslipoproteinemia in the metabolic syndrome.
2001
Treatment of nonalcoholic fatty liver: present and emerging therapies.
2001
[Rhabdomyolysis complicated with acute renal insufficiency in a patient treated with gemfibrozil and cerivastatin].
2001 Apr
Rhabdomyolysis after cerivastatin-gemfibrozil therapy in an HIV-infected patient with protease inhibitor-related hyperlipidemia.
2001 Apr 13
Rhabdomyolysis and acute renal failure following a switchover of therapy between two fibric acid derivatives.
2001 Aug
[Fatal rhabdomyolysis caused by cerivastatin].
2001 Aug
Effect of a six month gemfibrozil treatment and dietary recommendations on the metabolic risk profile of visceral obese men.
2001 Aug
Gemfibrozil treatment potentiates oxidative resistance of high-density lipoprotein in hypertriglyceridemic patients.
2001 Aug
PPARalpha-dependent induction of liver microsomal esterification of estradiol and testosterone by a prototypical peroxisome proliferator.
2001 Aug
A sensitive method for the determination of gemfibrozil in human plasma samples by RP-LC.
2001 Aug
Baycol withdrawn from market.
2001 Aug 21
[Lipid-lowering drugs].
2001 Dec
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
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
[Peroxisome proliferator-activated receptors (PPARs) in the vessel wall: new regulators of gene expression in vascular cells].
2001 Jul
Gemfibrozil improves insulin sensitivity and flow-mediated vasodilatation in type 2 diabetic patients.
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
Statin-fibrate combination therapy.
2001 Jul-Aug
Fibrate treatment can increase serum creatinine levels.
2001 Jun
Normocholesterolaemic dysslipidaemia: is there a role for fibrates?
2001 Jun 4
Normocholesterolaemic dyslipidaemia: is there a role for fibrates?
2001 Jun 4
[Gemfibrozil: new aspects in clinical use].
2001 Mar
[VA-HIT Study [Veterans Affairs High-Density Lipoprotein Cholesterol Intervention Trial Study]].
2001 Mar
Attenuation by fibrates of plasminogen activator inhibitor type-1 expression in human arterial smooth muscle cells.
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
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
[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
[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

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
Sustained potent reduction of [Ca²⁺]i in cultured rat VSMCs was observed with Gemfibrozil 50mg/L
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 MONOGRAPH]
Common Name English
GEMFIBROZIL [MART.]
Common Name English
GEMFIBROZIL [USAN]
Common Name English
GEMFIBROZIL [USP-RS]
Common Name English
GEMFIBROZIL [JAN]
Common Name English
NSC-757024
Code English
GEMFIBROZIL [ORANGE BOOK]
Common Name English
GEMFIBROZIL [WHO-DD]
Common Name English
GEMFIBROZIL [MI]
Common Name English
GEMFIBROZIL [INCI]
Common Name English
CI-719
Code English
GEMFIBROZIL [USP MONOGRAPH]
Common Name 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
FDA ORPHAN DRUG 591917
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
EU-Orphan Drug EU/3/18/1993
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
NCI_THESAURUS C98150
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
WHO-VATC QC10AB04
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
FDA ORPHAN DRUG 591917
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
FDA ORPHAN DRUG 546216
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
NDF-RT N0000170118
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
NDF-RT N0000175375
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
NDF-RT N0000175596
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
WHO-ATC C10AB04
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
NDF-RT N0000170118
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
LIVERTOX 452
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
Code System Code Type Description
CAS
25812-30-0
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
HSDB
7735
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
DRUG BANK
DB01241
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
247-280-2
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
INN
3899
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
USP_CATALOG
1288500
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY USP-RS
EPA CompTox
25812-30-0
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
EVMPD
SUB07894MIG
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
FDA UNII
Q8X02027X3
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
DRUG CENTRAL
1285
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
IUPHAR
3439
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
RXCUI
4719
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY RxNorm
MESH
D015248
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
LACTMED
Gemfibrozil
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
NCI_THESAURUS
C29071
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
MERCK INDEX
M5692
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL457
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
WIKIPEDIA
GEMFIBROZIL
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY
PUBCHEM
3463
Created by admin on Fri Jun 25 21:05:41 UTC 2021 , Edited by admin on Fri Jun 25 21:05:41 UTC 2021
PRIMARY