Identification

Name
Gemfibrozil
Accession Number
DB01241  (APRD00293)
Type
Small Molecule
Groups
Approved
Description

A lipid-regulating agent that lowers elevated serum lipids primarily by decreasing serum triglycerides with a variable reduction in total cholesterol. These decreases occur primarily in the VLDL fraction and less frequently in the LDL fraction. Gemfibrozil increases HDL subfractions HDL2 and HDL3 as well as apolipoproteins A-I and A-II. Its mechanism of action has not been definitely established.

Structure
Thumb
Synonyms
  • 2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeure
  • 2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure
  • 2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid
  • Gemfibrozil
  • Gemfibrozilo
  • Gemfibrozilum
External IDs
CI-719
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GemfibrozilTablet600 mg/1OralWatson Pharmaceuticals2007-01-01Not applicableUs
Gemfibrozil Cap 300mgCapsule300 mgOralOmni Laboratories Division, Warner Lambert Canada Inc.1990-12-312003-07-04Canada
Gemfibrozil Tab 600mgTablet600 mgOralOmni Laboratories Division, Warner Lambert Canada Inc.1991-12-312003-07-04Canada
Gemfibrozil-300 - CapCapsule300 mgOralPro Doc Limitee1995-12-312010-07-13Canada
Gemfibrozil-600 - Tab 600mgTablet600 mgOralPro Doc Limitee1995-12-312015-07-10Canada
LopidTablet, film coated600 mg/1OralPhysicians Total Care, Inc.2004-03-302012-06-30Us
LopidTablet, film coated600 mg/1OralParke Davis Div Of Pfizer Inc2004-03-30Not applicableUs
LopidTablet, film coated600 mg/1OralRemedy Repack2017-08-16Not applicableUs
Lopid 600mgTablet600 mgOralPfizer1987-12-312013-07-18Canada
Lopid Cap 300mgCapsule300 mgOralPfizer1984-12-312013-07-18Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-gemfibrozilTablet600 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-gemfibrozil Cap 300mg USPCapsule300 mgOralApotex Corporation1993-12-31Not applicableCanada
Dom-gemfibrozilTablet600 mgOralDominion Pharmacal1998-10-222013-04-05Canada
Dom-gemfibrozilCapsule300 mgOralDominion Pharmacal2000-03-10Not applicableCanada
GemfibrozilTablet, film coated600 mg/1OralMajor2004-02-062015-09-30Us
GemfibrozilTablet600 mg/1OralNucare Pharmaceuticals,inc.2016-10-13Not applicableUs
GemfibrozilTablet, film coated600 mg/1OralWest Ward Pharmaceutical2006-07-27Not applicableUs0143 913020180907 15195 n8sj11
GemfibrozilTablet600 mg/1Oralbryant ranch prepack2017-03-23Not applicableUs
GemfibrozilTablet600 mg/1OralNorthwind Pharmaceuticals2014-10-23Not applicableUs
GemfibrozilTablet, film coated600 mg/1Oralbryant ranch prepack2015-09-16Not applicableUs
International/Other Brands
Gemlipid (Farmellas Enterprises) / Gen-Fibro / Genlip (Teofarma) / Jezil / Lipur (Pfizer) / Lopid
Categories
UNII
Q8X02027X3
CAS number
25812-30-0
Weight
Average: 250.3334
Monoisotopic: 250.15689457
Chemical Formula
C15H22O3
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

Pharmacology

Indication

For treatment of adult patients with very high elevations of serum triglyceride levels (types IV and V hyperlipidemia) who are at risk of developing pancreatitis (inflammation of the pancreas) and who do not respond adequately to a strict diet.

Associated Conditions
Pharmacodynamics

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).

Mechanism of action

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.

TargetActionsOrganism
APeroxisome proliferator-activated receptor alpha
agonist
Human
Absorption

Well absorbed from gastrointestinal tract (within 1-2 hours).

Volume of distribution
Not Available
Protein binding

95%

Metabolism

Hepatic. Gemfibrozil mainly undergoes oxidation of a ring methyl group to successively form a hydroxymethyl and a carboxyl metabolite.

Route of elimination

Approximately seventy percent of the administered human dose is excreted in the urine, mostly as the glucuronide conjugate, with less than 2% excreted as unchanged gemfibrozil.

Half life

1.5 hours

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 3162 mg/kg. Symptoms of overdose include abdominal cramps, diarrhea, joint and muscle pain, nausea, and vomiting.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Gemfibrozil.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Gemfibrozil.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Gemfibrozil.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Gemfibrozil.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Gemfibrozil.
6-Deoxyerythronolide BThe metabolism of Gemfibrozil can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Gemfibrozil.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Gemfibrozil.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Gemfibrozil.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Gemfibrozil.
Food Interactions
  • Take 30 minutes before meals.

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
Not Available
External Links
Human Metabolome Database
HMDB0015371
KEGG Drug
D00334
KEGG Compound
C07020
PubChem Compound
3463
PubChem Substance
46508264
ChemSpider
3345
BindingDB
50110590
ChEBI
5296
ChEMBL
CHEMBL457
Therapeutic Targets Database
DAP000210
PharmGKB
PA449750
IUPHAR
3439
Guide to Pharmacology
GtP Drug Page
HET
4TX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Gemfibrozil
ATC Codes
C10AB04 — Gemfibrozil
AHFS Codes
  • 24:06.06 — Fribic Acid Derivatives
PDB Entries
5boj
FDA label
Download (260 KB)
MSDS
Download (74.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingPreventionPreclinical Alzheimer's Disease1
1CompletedNot AvailableDrug Drug Interaction (DDI) / Healthy Volunteers / Pharmacokinetics1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedOtherAnemias1
1CompletedTreatmentBioavailability1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHypertriglyceridemias1
1CompletedTreatmentMalignancies1
1CompletedTreatmentType 2 Diabetes Mellitus2
1RecruitingBasic ScienceHealthy Volunteers1
1RecruitingTreatmentDrug Drug Interaction (DDI)1
2CompletedTreatmentCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia1
2CompletedTreatmentNicotine Dependence1
2RecruitingTreatmentCessation, Smoking1
3CompletedTreatmentCoronary Heart Disease (CHD)1
4CompletedTreatmentIron Deficiency Anemia (IDA)1
4WithdrawnTreatmentAtherosclerosis1
Not AvailableCompletedNot AvailableHealthy Volunteers1

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
FormRouteStrength
TabletOral600 mg/1
Tablet, coatedOral600 mg/1
Tablet, film coatedOral600 mg/1
CapsuleOral300 mg
TabletOral600 mg
Prices
Unit descriptionCostUnit
Gemfibrozil powder2.88USD g
Lopid 600 mg tablet2.07USD tablet
Gemfibrozil 600 mg tablet1.8USD tablet
Apo-Gemfibrozil 600 mg Tablet0.65USD tablet
Mylan-Gemfibrozil 600 mg Tablet0.65USD tablet
Novo-Gemfibrozil 600 mg Tablet0.65USD tablet
Nu-Gemfibrozil 600 mg Tablet0.65USD tablet
Pms-Gemfibrozil 600 mg Tablet0.65USD tablet
Lopid 300 mg Capsule0.58USD capsule
Apo-Gemfibrozil 300 mg Capsule0.31USD capsule
Mylan-Gemfibrozil 300 mg Capsule0.31USD capsule
Novo-Gemfibrozil 300 mg Capsule0.31USD capsule
Nu-Gemfibrozil 300 mg Capsule0.31USD capsule
Pms-Gemfibrozil 300 mg Capsule0.31USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)62 °CPhysProp
boiling point (°C)158.5 °C at 2.00E-02 mm HgPhysProp
water solubility10 mg/mL (in base)Not Available
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0278 mg/mLALOGPS
logP3.61ALOGPS
logP4.39ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.42ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.82 m3·mol-1ChemAxon
Polarizability28.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.977
Blood Brain Barrier+0.9213
Caco-2 permeable+0.7918
P-glycoprotein substrateSubstrate0.5597
P-glycoprotein inhibitor INon-inhibitor0.8943
P-glycoprotein inhibitor IINon-inhibitor0.8839
Renal organic cation transporterNon-inhibitor0.8177
CYP450 2C9 substrateNon-substrate0.7512
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6973
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8234
Ames testNon AMES toxic0.7822
CarcinogenicityNon-carcinogens0.8314
BiodegradationNot ready biodegradable0.6759
Rat acute toxicity2.2167 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9774
hERG inhibition (predictor II)Non-inhibitor0.8701
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-24b892a8bd68bdf9cef6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-7a9eaaae65f0e1efcbc4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-12b36ea4be2a1b876c61
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-647692900acca2ec2441
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-41c8e4e08162dfaf1fc4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-28d25da91cc1d391cc84
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0900000000-a08267bdc97edb1a2601
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0900000000-a133a90a69b988c45ffb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0059-6910000000-0ad597adcb83e9f4e4ba
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0059-8900000000-8684ba342d3eb0a7f602
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05cr-9400000000-008385b887cc6ac6d748
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ac0-9300000000-74e1b5c007dd49af6a01
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ab9-9200000000-cc36aaee7c70d8e92f96
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9100000000-ce28ed926945c33079d6
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Phenoxy compound / P-xylene / Xylene / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Carboxylic acid derivative / Carboxylic acid / Ether / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether (CHEBI:5296)

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10494028]
  2. 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. [PubMed:12172398]
  3. 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. [PubMed:12244038]
  4. 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. [PubMed:12834305]
  5. 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. [PubMed:12935323]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
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
  1. 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. [PubMed:22472994]
  2. 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. [PubMed:12433802]
  3. 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. [PubMed:26721703]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:11602509]
Kind
Protein
Organism
Human
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:11602509]
Details
4. Cytochrome P450 2C9
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11602509]
  2. 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. [PubMed:17333159]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inhibitor
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
  1. 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. [PubMed:21175442]
  2. 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. [PubMed:15304429]
  3. FDA Label - ONIVYDE™ (irinotecan liposome injection) [File]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:9515185]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:19919292]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2018 07:57