Identification
- Summary
Gemfibrozil is a lipid regulator that is used in the reduction of serum triglyceride levels in high-risk patients with hyperlipidemia.
- Brand Names
- Lopid
- Generic Name
- Gemfibrozil
- DrugBank Accession Number
- DB01241
- Background
Gemfibrozil is a fibric acid agent, similar to clofibrate, used to treat Type IIb, IV, and V hyperlipidemias.3,11 Gemfibrozil is not a first line treatment and is prescribed to patients who have not responded adequately to weight loss, diet, exercise, and other medications.11
Gemfibrozil was granted FDA approval on 21 December 1981.11
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Gemfibrozil (DB01241)
- Weight
- Average: 250.3334
Monoisotopic: 250.15689457 - Chemical Formula
- C15H22O3
- Synonyms
- 2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansäure
- 2,2-Dimethyl-5-(2,5-xylyloxy)valeriansäure
- 2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid
- Gemfibrozil
- Gemfibrozilo
- Gemfibrozilum
- External IDs
- CI-719
Pharmacology
- Indication
Gemfibrozil is indicated to treat patients with Types IV and V hyperlipidemia who have elevated serum triglycerides (usually above 2000mg/dL), elevated VLDL cholesterol, fasting chylomicrons, are at risk of developing pancreatitis, and do not adequately respond to dietary restrictions.11 Gemfibrozil is also indicated to reduce the risk of developing coronary heart disease in patients with Type IIb hyperlipidemia without history or symptoms of coronary heart disease; who do not adequately respond to weight loss, diet, exercise, and other medications; and have low HDL, raised LDL, and raised triglycerides.11
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Coronary heart disease •••••••••••• Management of Frederickson type iv hypertriglyceridemia •••••••••••• Management of Frederickson type v hypertriglyceridemia •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Gemfibrozil alters lipid metabolism to treat patients with hyperlipidemia.11 The duration of action requires twice daily dosing as the mean residence time of gemfibrozil is up to 9.6h in patients with chronic renal failure.7 Gemfibrozil has a wide therapeutic index as trials with twice the standard dose were not associated with severe side effects.8,11 Patients taking gemfibrozil may be at an increased risk of developing cholelithiasis and cholecystitis, as seen in patients taking clofibrate.11
- Mechanism of action
Gemfibrozil activates peroxisome proliferator-activated receptor-α (PPARα), which alters lipid metabolism.3 This activation leads to increased HDL, apo AI, apo AII, lipoprotein lipase (LPL), inhibition of apo B synthesis, peripheral lipolysis, decreased removal of free fatty acids by the liver, and increased clearance of apoB.1,3,11
Upregulated LPL reduces plasma triglyceride levels.1,3,11 Decreased hepatic removal of fatty acids decreases the production of triglycerides.1,3,11 The effects on apoB synthesis and clearance decrease VLDL production which also reduce plasma triglyceride levels.1,3,11
Gemfibrozil's glucuronide metabolite is also an inhibitor of CYP2C8.4
Target Actions Organism APeroxisome proliferator-activated receptor alpha agonistHumans USolute carrier organic anion transporter family member 1B1 inhibitorHumans USolute carrier family 22 member 8 inhibitorHumans USolute carrier organic anion transporter family member 2B1 inhibitorHumans USolute carrier organic anion transporter family member 1B3 inhibitorHumans - Absorption
Gemfibrozil is absorbed from the gastrointestinal tract.11
In healthy volunteers, a 900mg oral dose of gemfibrozil has a Cmax of 46±16µg/mL with a Tmax of 2.2±1.1h.7 In patients with chronic renal failure, gemfibrozil has a Cmax of 13.8±11.1µg/mL with a Tmax of 2.3±1.0h.7 In patients with liver disease, gemfibrozil has a Cmax of 23.0±10.3µg/mL with a Tmax of 2.6±1.7h.7
- Volume of distribution
The volume of distribution of gemfibrozil is estimated to be 0.8L/kg.10
- Protein binding
Gemfibrozil is 99% protein bound.3,6 It is 98.6% bound to serum albumin, 0.8% bound to erythrocytes, and 0.8% unbound.5,6 There is negligible binding to alpha-1-acid glycoprotein.6
- Metabolism
Gemfibrozil undergoes hydroxylation at the 5'-methyl and 4' positions to form the M1 and M2 metaolites respectively9. Gemfibrozil also undergoes O-glucuronidation to form gemfibrozil 1-beta glucuronide, an inhibitor of CYP2C8.4 This O-glucuronidation is primarily mediated by UGT2B7, but also by UGT1A1, UGT1A3, UGT1A9, UGT2B4, UGT2B17.4
Hover over products below to view reaction partners
- Route of elimination
Approximately 70% of a dose of gemfibrozil is eliminated in the urine.11 The majority of a dose is eliminated as a glucuronide conjugate and <2% is elimiinated as the unmetabolized drug.11 6% of a dose is eliminated in the feces.11
In healthy volunteers, 0.02-0.15% of a dose was detected in the urine as unmetabolized gemfibrozil, with 7-14% detected as conjugated metabolites.7 In patients with renal failure, trace amounts of unmetabolized gemfibrozil is present in the urine, with 0.5-9.8% detected as conjugated metabolites.7 In patients with liver disease, 0.1-0.2% of a dose was detected in the urine as unmetabolized gemfibrozil, with 25-50% detected as conjugated metabolites.7
- Half-life
Gemfibrozil has a plasma half-life of 1.5 hours.11 In patients with renal failure the half life is 2.4h and in patients with liver disease the half life is 2.1h.7
- Clearance
The clearance of gemfibrozil is estimated to be 6.0L/h.10
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral TDLO of gemfibrozil in humans is 18gm/kg/3Y.12 The oral LD50 in mice is 2218mg/kg and in rats is 1414mg/kg.12 The intraperitoneal LD50 in rats is 445mg/kg.12
Patients experiencing an overdose may present with abdominal cramps, adnormal liver function tests, diarrhea, increased CPK, joint and muscle pain, nausea, and vomiting.11 Patients should be treated with symptomatic and supportive measures.11
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir The metabolism of Abacavir can be decreased when combined with Gemfibrozil. Abametapir The serum concentration of Gemfibrozil can be increased when it is combined with Abametapir. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Gemfibrozil. Acamprosate The excretion of Acamprosate can be decreased when combined with Gemfibrozil. Aceclofenac Aceclofenac may decrease the excretion rate of Gemfibrozil which could result in a higher serum level. - Food Interactions
- Take before a meal. Take 30 minutes before meals.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Gemlipid (Farmellas Enterprises) / Gen-Fibro / Genlip (Teofarma) / Jezil / Lipur (Pfizer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Gemfibrozil Tablet 600 mg/1 Oral Watson Pharmaceuticals 2007-01-01 Not applicable US 
Gemfibrozil Cap 300mg Capsule 300 mg / cap Oral Omni Laboratories Division, Warner Lambert Canada Inc. 1990-12-31 2003-07-04 Canada 
Gemfibrozil Tab 600mg Tablet 600 mg Oral Omni Laboratories Division, Warner Lambert Canada Inc. 1991-12-31 2003-07-04 Canada Gemfibrozil-300 - Cap Capsule 300 mg Oral Pro Doc Limitee 1995-12-31 2010-07-13 Canada Gemfibrozil-600 - Tab 600mg Tablet 600 mg Oral Pro Doc Limitee 1995-12-31 2015-07-10 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-gemfibrozil Tablet 600 mg Oral Apotex Corporation 1993-12-31 Not applicable Canada Apo-gemfibrozil Cap 300mg USP Capsule 300 mg Oral Apotex Corporation 1993-12-31 Not applicable Canada Dom-gemfibrozil Capsule 300 mg Oral Dominion Pharmacal 2000-03-10 Not applicable Canada Dom-gemfibrozil Tablet 600 mg Oral Dominion Pharmacal 1998-10-22 2013-04-05 Canada Gemfibrozil Tablet 600 mg/1 Oral Denton Pharma, Inc. Dba Northwind Pharmaceuticals 2019-01-22 2024-03-31 US
Categories
- ATC Codes
- C10AB04 — Gemfibrozil
- Drug Categories
- Acids, Acyclic
- Agents Causing Muscle Toxicity
- Benzene Derivatives
- Butyrates
- Chemically-Induced Disorders
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (strong)
- Cytochrome P-450 CYP2C8 Inducers
- Cytochrome P-450 CYP2C8 Inducers (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strong)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strong)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Ethers
- Fatty Acids
- Fatty Acids, Volatile
- Fibric Acid Derivatives
- Fibric Acids
- Hypolipidemic Agents
- Hypolipidemic Agents Indicated for Hyperlipidemia
- Isobutyrates
- Lipid Modifying Agents
- Lipid Modifying Agents, Plain
- Lipid Regulating Agents
- Lipids
- Non-statin Hypolipidemic Agents Indicated for Hyperlipidemia
- Noxae
- OAT3/SLC22A8 Inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Pentanoic Acids
- Peroxisome Proliferator Receptor alpha Agonist
- Peroxisome Proliferator-activated Receptor alpha Agonists
- Phenols
- Phenyl Ethers
- Photosensitizing Agents
- Toxic Actions
- UGT1A1 Inhibitors
- UGT1A1 Substrates
- UGT1A3 Inhibitors
- UGT1A3 substrates
- UGT1A9 Substrates
- UGT2B17 substrates
- UGT2B7 substrates
- Valerates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- p-Xylenes / Phenoxy compounds / Alkyl aryl ethers / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alkyl aryl ether / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Ether / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic oxide
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aromatic ether (CHEBI:5296)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Q8X02027X3
- CAS number
- 25812-30-0
- InChI Key
- HEMJJKBWTPKOJG-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid
- SMILES
- CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1
References
- Synthesis Reference
Gianfranco Piccoli, Antonio Tarquini, Giovanni Frare, "Process for the preparation of gemfibrozil." U.S. Patent US5654476, issued May, 1980.
US5654476- General References
- Saku K, Gartside PS, Hynd BA, Kashyap ML: Mechanism of action of gemfibrozil on lipoprotein metabolism. J Clin Invest. 1985 May;75(5):1702-12. doi: 10.1172/JCI111879. [Article]
- Okerholm RA, Keeley FJ, Peterson FE, Glazko AJ: The metabolism of gemfibrozil. Proc R Soc Med. 1976;69 Suppl 2:11-4. [Article]
- Quintanilla Rodriguez BS, Correa R: Gemfibrozil . [Article]
- Mano Y, Usui T, Kamimura H: The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4. doi: 10.1124/dmd.107.017269. Epub 2007 Aug 1. [Article]
- Sallustio BC, Fairchild BA, Pannall PR: Interaction of human serum albumin with the electrophilic metabolite 1-O-gemfibrozil-beta-D-glucuronide. Drug Metab Dispos. 1997 Jan;25(1):55-60. [Article]
- Hamberger C, Barre J, Zini R, Taiclet A, Houin G, Tillement JP: In vitro binding study of gemfibrozil to human serum proteins and erythrocytes: interactions with other drugs. Int J Clin Pharmacol Res. 1986;6(6):441-9. [Article]
- Knauf H, Kolle EU, Mutschler E: Gemfibrozil absorption and elimination in kidney and liver disease. Klin Wochenschr. 1990 Jul 5;68(13):692-8. doi: 10.1007/bf01667018. [Article]
- Fereshetian AG, Davidson M, Haber H, Black DM: Gemfibrozil treatment in patients with elevated lipoprotein a: a pilot study. Clin Drug Investig. 1998;16(1):1-7. doi: 10.2165/00044011-199816010-00001. [Article]
- Takahiro M, Haruo I, Toshihiko, I: Identification of Gemfibrozil Metabolites, Produced as Positional Isomers in Human Liver Microsomes, by On-line Analyses Using Liquid Chromatography/Mass Spectrometry and Liquid Chromatography/Nuclear Magnetic Resonance Spectroscopy J. Mass Spectrom. Soc. Jpn.. 2004 Jun 6;52(5):277-283. [Article]
- Varma MV, Lin J, Bi YA, Kimoto E, Rodrigues AD: Quantitative Rationalization of Gemfibrozil Drug Interactions: Consideration of Transporters-Enzyme Interplay and the Role of Circulating Metabolite Gemfibrozil 1-O-beta-Glucuronide. Drug Metab Dispos. 2015 Jul;43(7):1108-18. doi: 10.1124/dmd.115.064303. Epub 2015 May 4. [Article]
- FDA Approved Drug Products: Gemfibrozil Oral Tablets [Link]
- Cayman Chemicals: Gemfibrozil MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0015371
- KEGG Drug
- D00334
- KEGG Compound
- C07020
- PubChem Compound
- 3463
- PubChem Substance
- 46508264
- ChemSpider
- 3345
- BindingDB
- 50110590
- 4719
- ChEBI
- 5296
- ChEMBL
- CHEMBL457
- ZINC
- ZINC000001530641
- Therapeutic Targets Database
- DAP000210
- PharmGKB
- PA449750
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- 4TX
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Gemfibrozil
- PDB Entries
- 5boj / 7qfe
- FDA label
- Download (260 KB)
- MSDS
- Download (74.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Healthy Subjects (HS) 1 4 Withdrawn Treatment Atherosclerosis 1 3 Completed Treatment Coronary Heart Disease (CHD) 1 3 Not Yet Recruiting Treatment Juvenile Neuronal Ceroid Lipofuscinosis (CLN3, Batten Disease) 1 2 Completed Treatment Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Myocardial Ischemia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Ancheng Pharma Limited
- Apotex Inc.
- Blu Pharmaceuticals LLC
- Bryant Ranch Prepack
- Camber Pharmaceuticals Inc.
- Caraco Pharmaceutical Labs
- Cardinal Health
- Corepharma LLC
- Coupler Enterprises Inc.
- DAVA Pharmaceuticals
- Dept Health Central Pharmacy
- DHHS Program Support Center Supply Service Center
- Direct Dispensing Inc.
- Dispensing Solutions
- Global Pharmaceuticals
- Golden State Medical Supply Inc.
- Heartland Repack Services LLC
- InvaGen Pharmaceuticals Inc.
- Kaiser Foundation Hospital
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Murfreesboro Pharmaceutical Nursing Supply
- Norwich Pharmaceuticals Inc.
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Patheon Inc.
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Professional Co.
- Rebel Distributors Corp.
- Remedy Repack
- Sandhills Packaging Inc.
- Southwood Pharmaceuticals
- Sun Pharmaceutical Industries Ltd.
- Teva Pharmaceutical Industries Ltd.
- Torpharm Inc.
- Tya Pharmaceuticals
- UDL Laboratories
- Va Cmop Dallas
- Vangard Labs Inc.
- Watson Pharmaceuticals
- West-Ward Pharmaceuticals
- Zydus Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet Oral 300 mg Tablet Oral Granule 1200 MG Tablet Oral 600 mg/1 Tablet Oral 900 MG Tablet, coated Oral 600 mg/1 Tablet, film coated Oral 600 mg/1 Capsule Oral 300 mg / cap Tablet, coated Oral 60000000 mg Tablet, film coated Oral 900 mg Tablet, delayed release Oral 600 mg Tablet, coated Oral Capsule Oral 600 mg Capsule, coated Oral 300 mg Granule, for suspension Oral 1200 mg Granule, for suspension Oral 900 mg Tablet, film coated Oral Granule Granule, for suspension Oral Capsule Oral Granule 900 MG Tablet Oral 900.000 mg Tablet Oral 600 mg / tab Tablet Oral 600.00 mg Capsule Oral 300 mg Tablet, coated Oral 900 mg Tablet, coated Oral 600 mg Tablet, film coated Oral 600 mg Tablet Oral 600 mg - Prices
Unit description Cost Unit Gemfibrozil powder 2.88USD g Lopid 600 mg tablet 2.07USD tablet Gemfibrozil 600 mg tablet 1.8USD tablet Apo-Gemfibrozil 600 mg Tablet 0.65USD tablet Mylan-Gemfibrozil 600 mg Tablet 0.65USD tablet Novo-Gemfibrozil 600 mg Tablet 0.65USD tablet Nu-Gemfibrozil 600 mg Tablet 0.65USD tablet Pms-Gemfibrozil 600 mg Tablet 0.65USD tablet Lopid 300 mg Capsule 0.58USD capsule Apo-Gemfibrozil 300 mg Capsule 0.31USD capsule Mylan-Gemfibrozil 300 mg Capsule 0.31USD capsule Novo-Gemfibrozil 300 mg Capsule 0.31USD capsule Nu-Gemfibrozil 300 mg Capsule 0.31USD capsule Pms-Gemfibrozil 300 mg Capsule 0.31USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 58-61 FDA Label boiling point (°C) 158.5 °C at 2.00E-02 mm Hg PhysProp logP 4.387 ChemSpider - Predicted Properties
Property Value Source Water Solubility 0.0278 mg/mL ALOGPS logP 3.61 ALOGPS logP 4.39 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 4.42 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 71.82 m3·mol-1 Chemaxon Polarizability 28.9 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.977 Blood Brain Barrier + 0.9213 Caco-2 permeable + 0.7918 P-glycoprotein substrate Substrate 0.5597 P-glycoprotein inhibitor I Non-inhibitor 0.8943 P-glycoprotein inhibitor II Non-inhibitor 0.8839 Renal organic cation transporter Non-inhibitor 0.8177 CYP450 2C9 substrate Non-substrate 0.7512 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6973 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8234 Ames test Non AMES toxic 0.7822 Carcinogenicity Non-carcinogens 0.8314 Biodegradation Not ready biodegradable 0.6759 Rat acute toxicity 2.2167 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9774 hERG inhibition (predictor II) Non-inhibitor 0.8701
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 168.9544048 predictedDarkChem Lite v0.1.0 [M-H]- 169.4125048 predictedDarkChem Lite v0.1.0 [M-H]- 168.9918048 predictedDarkChem Lite v0.1.0 [M-H]- 164.49422 predictedDeepCCS 1.0 (2019) [M+H]+ 169.3420048 predictedDarkChem Lite v0.1.0 [M+H]+ 169.1184048 predictedDarkChem Lite v0.1.0 [M+H]+ 169.5334048 predictedDarkChem Lite v0.1.0 [M+H]+ 166.85222 predictedDeepCCS 1.0 (2019) [M+Na]+ 169.3135048 predictedDarkChem Lite v0.1.0 [M+Na]+ 169.2560048 predictedDarkChem Lite v0.1.0 [M+Na]+ 169.0482048 predictedDarkChem Lite v0.1.0 [M+Na]+ 172.94537 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
- Gene Name
- PPARA
- Uniprot ID
- Q07869
- Uniprot Name
- Peroxisome proliferator-activated receptor alpha
- Molecular Weight
- 52224.595 Da
References
- Clavey V, Copin C, Mariotte MC, Bauge E, Chinetti G, Fruchart J, Fruchart JC, Dallongeville J, Staels B: Cell culture conditions determine apolipoprotein CIII secretion and regulation by fibrates in human hepatoma HepG2 cells. Cell Physiol Biochem. 1999;9(3):139-49. [Article]
- Bosse Y, Pascot A, Dumont M, Brochu M, Prud'homme D, Bergeron J, Despres JP, Vohl MC: Influences of the PPAR alpha-L162V polymorphism on plasma HDL(2)-cholesterol response of abdominally obese men treated with gemfibrozil. Genet Med. 2002 Jul-Aug;4(4):311-5. [Article]
- Pahan K, Jana M, Liu X, Taylor BS, Wood C, Fischer SM: Gemfibrozil, a lipid-lowering drug, inhibits the induction of nitric-oxide synthase in human astrocytes. J Biol Chem. 2002 Nov 29;277(48):45984-91. Epub 2002 Sep 18. [Article]
- Shoji Y, Sanekata A, Sato M, Imaizumi K: Preparation of antiserum against rat delta6-desaturase and its use to evaluate the desaturase protein levels in rats treated with gemfibrozil, a ligand for peroxisome proliferator-activated receptor alpha. Biosci Biotechnol Biochem. 2003 May;67(5):1177-8. [Article]
- Rizvi F, Iftikhar M, George JP: Beneficial effects of fish liver preparations of sea bass (Lates calcarifer) versus gemfibrozil in high fat diet-induced lipid-intolerant rats. J Med Food. 2003 Summer;6(2):123-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Sharma P, Holmes VE, Elsby R, Lambert C, Surry D: Validation of cell-based OATP1B1 assays to assess drug transport and the potential for drug-drug interaction to support regulatory submissions. Xenobiotica. 2010 Jan;40(1):24-37. doi: 10.3109/00498250903351013. [Article]
- Varma MV, Lin J, Bi YA, Kimoto E, Rodrigues AD: Quantitative Rationalization of Gemfibrozil Drug Interactions: Consideration of Transporters-Enzyme Interplay and the Role of Circulating Metabolite Gemfibrozil 1-O-beta-Glucuronide. Drug Metab Dispos. 2015 Jul;43(7):1108-18. doi: 10.1124/dmd.115.064303. Epub 2015 May 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Varma MV, Lin J, Bi YA, Kimoto E, Rodrigues AD: Quantitative Rationalization of Gemfibrozil Drug Interactions: Consideration of Transporters-Enzyme Interplay and the Role of Circulating Metabolite Gemfibrozil 1-O-beta-Glucuronide. Drug Metab Dispos. 2015 Jul;43(7):1108-18. doi: 10.1124/dmd.115.064303. Epub 2015 May 4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- Noe J, Portmann R, Brun ME, Funk C: Substrate-dependent drug-drug interactions between gemfibrozil, fluvastatin and other organic anion-transporting peptide (OATP) substrates on OATP1B1, OATP2B1, and OATP1B3. Drug Metab Dispos. 2007 Aug;35(8):1308-14. doi: 10.1124/dmd.106.012930. Epub 2007 Apr 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Noe J, Portmann R, Brun ME, Funk C: Substrate-dependent drug-drug interactions between gemfibrozil, fluvastatin and other organic anion-transporting peptide (OATP) substrates on OATP1B1, OATP2B1, and OATP1B3. Drug Metab Dispos. 2007 Aug;35(8):1308-14. doi: 10.1124/dmd.106.012930. Epub 2007 Apr 30. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Honkalammi J, Niemi M, Neuvonen PJ, Backman JT: Gemfibrozil is a strong inactivator of CYP2C8 in very small multiple doses. Clin Pharmacol Ther. 2012 May;91(5):846-55. doi: 10.1038/clpt.2011.313. [Article]
- Wang JS, Neuvonen M, Wen X, Backman JT, Neuvonen PJ: Gemfibrozil inhibits CYP2C8-mediated cerivastatin metabolism in human liver microsomes. Drug Metab Dispos. 2002 Dec;30(12):1352-6. [Article]
- Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Wen X, Wang JS, Backman JT, Kivisto KT, Neuvonen PJ: Gemfibrozil is a potent inhibitor of human cytochrome P450 2C9. Drug Metab Dispos. 2001 Nov;29(11):1359-61. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Wen X, Wang JS, Backman JT, Kivisto KT, Neuvonen PJ: Gemfibrozil is a potent inhibitor of human cytochrome P450 2C9. Drug Metab Dispos. 2001 Nov;29(11):1359-61. [Article]
- Tornio A, Niemi M, Neuvonen PJ, Backman JT: Stereoselective interaction between the CYP2C8 inhibitor gemfibrozil and racemic ibuprofen. Eur J Clin Pharmacol. 2007 May;63(5):463-9. doi: 10.1007/s00228-007-0273-9. Epub 2007 Feb 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data supported only by in vitro studies.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Wen X, Wang JS, Backman JT, Kivisto KT, Neuvonen PJ: Gemfibrozil is a potent inhibitor of human cytochrome P450 2C9. Drug Metab Dispos. 2001 Nov;29(11):1359-61. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Miller DB, Spence JD: Clinical pharmacokinetics of fibric acid derivatives (fibrates). Clin Pharmacokinet. 1998 Feb;34(2):155-62. doi: 10.2165/00003088-199834020-00003. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Mano Y, Usui T, Kamimura H: The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4. doi: 10.1124/dmd.107.017269. Epub 2007 Aug 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Gan J, Chen W, Shen H, Gao L, Hong Y, Tian Y, Li W, Zhang Y, Tang Y, Zhang H, Humphreys WG, Rodrigues AD: Repaglinide-gemfibrozil drug interaction: inhibition of repaglinide glucuronidation as a potential additional contributing mechanism. Br J Clin Pharmacol. 2010 Dec;70(6):870-80. doi: 10.1111/j.1365-2125.2010.03772.x. [Article]
- Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]
- Mano Y, Usui T, Kamimura H: The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4. doi: 10.1124/dmd.107.017269. Epub 2007 Aug 1. [Article]
- FDA Label - ONIVYDE™ (irinotecan liposome injection) [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
References
- Gill KL, Houston JB, Galetin A: Characterization of in vitro glucuronidation clearance of a range of drugs in human kidney microsomes: comparison with liver and intestinal glucuronidation and impact of albumin. Drug Metab Dispos. 2012 Apr;40(4):825-35. doi: 10.1124/dmd.111.043984. Epub 2012 Jan 24. [Article]
- Gan J, Chen W, Shen H, Gao L, Hong Y, Tian Y, Li W, Zhang Y, Tang Y, Zhang H, Humphreys WG, Rodrigues AD: Repaglinide-gemfibrozil drug interaction: inhibition of repaglinide glucuronidation as a potential additional contributing mechanism. Br J Clin Pharmacol. 2010 Dec;70(6):870-80. doi: 10.1111/j.1365-2125.2010.03772.x. [Article]
- Hirvensalo P, Tornio A, Neuvonen M, Tapaninen T, Paile-Hyvarinen M, Karja V, Mannisto VT, Pihlajamaki J, Backman JT, Niemi M: Comprehensive Pharmacogenomic Study Reveals an Important Role of UGT1A3 in Montelukast Pharmacokinetics. Clin Pharmacol Ther. 2018 Jul;104(1):158-168. doi: 10.1002/cpt.891. Epub 2017 Nov 6. [Article]
- Mano Y, Usui T, Kamimura H: The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4. doi: 10.1124/dmd.107.017269. Epub 2007 Aug 1. [Article]
- DRUG-DRUG INTERACTIONS – FROM KNOWLEDGE BASE TO CLINICAL IMPACT [File]
- The UDP-Glucuronosyltransferase 2B7 Isozyme Is Responsible for Gemfibrozil Glucuronidation in the Human Liver [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- Mano Y, Usui T, Kamimura H: The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4. doi: 10.1124/dmd.107.017269. Epub 2007 Aug 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
- Gene Name
- UGT2B4
- Uniprot ID
- P06133
- Uniprot Name
- UDP-glucuronosyltransferase 2B4
- Molecular Weight
- 60512.035 Da
References
- Mano Y, Usui T, Kamimura H: The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4. doi: 10.1124/dmd.107.017269. Epub 2007 Aug 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbe...
- Gene Name
- UGT2B17
- Uniprot ID
- O75795
- Uniprot Name
- UDP-glucuronosyltransferase 2B17
- Molecular Weight
- 61094.915 Da
References
- Mano Y, Usui T, Kamimura H: The UDP-glucuronosyltransferase 2B7 isozyme is responsible for gemfibrozil glucuronidation in the human liver. Drug Metab Dispos. 2007 Nov;35(11):2040-4. doi: 10.1124/dmd.107.017269. Epub 2007 Aug 1. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Sallustio BC, Fairchild BA, Pannall PR: Interaction of human serum albumin with the electrophilic metabolite 1-O-gemfibrozil-beta-D-glucuronide. Drug Metab Dispos. 1997 Jan;25(1):55-60. [Article]
- Hamberger C, Barre J, Zini R, Taiclet A, Houin G, Tillement JP: In vitro binding study of gemfibrozil to human serum proteins and erythrocytes: interactions with other drugs. Int J Clin Pharmacol Res. 1986;6(6):441-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54