NAV

Clofibrate

Identification

Summary

Clofibrate is a fibric acid derivative used to treat hypertriglyceridemia and high cholesterol.

Generic Name
Clofibrate
DrugBank Accession Number
DB00636
Background

A fibric acid derivative used in the treatment of hyperlipoproteinemia type III and severe hypertriglyceridemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p986)

Type
Small Molecule
Groups
Approved, Investigational
Structure
3D
Similar Structures
Weight
Average: 242.699
Monoisotopic: 242.070972053
Chemical Formula
C12H15ClO3
Synonyms
  • 2-(4-Chlorophenoxy)-2-methylpropanoic acid ethyl ester
  • 2-(p-Chlorophenoxy)-2-methylpropionic acid ethyl ester
  • alpha-(p-Chlorophenoxy)isobutyric acid, ethyl ester
  • alpha-p-Chlorophenoxyisobutyryl ethyl ester
  • Clofibrate
  • Clofibrato
  • Clofibratum
  • EPIB
  • Ethyl 2-(p-chlorophenoxy)isobutyrate
  • Ethyl chlorophenoxyisobutyrate
  • Ethyl clofibrate
  • Liprin
External IDs
  • AY-61123
  • ICI 28257
  • ICI-28257
  • NSC-79389
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Pharmacology

Indication

For Primary Dysbetalipoproteinemia (Type III hyperlipidemia) that does not respond adequately to diet. This helps control high cholesterol and high triglyceride levels.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Clofibrate is an antilipidemic agent similar to gemfibrozil. It acts to lower elevated serum lipids by reducing the very low-density lipoprotein fraction (Sf 20-400) rich in triglycerides. Serum cholesterol may be decreased, particularly in those patients whose cholesterol elevation is due to the presence of IDL as a result of Type III hyperlipoproteinemia. Several investigators have observed in their studies that clofibrate may produce a decrease in cholesterol linoleate but an increase in palmitoleate and oleate, the latter being considered atherogenic in experimental animals. The significance of this finding is unknown at this time. Reduction of triglycerides in some patients treated with clofibrate or certain of its chemically and clinically similar analogs may be associated with an increase in LDL cholesterol. Increase in LDL cholesterol has been observed in patients whose cholesterol is initially normal. Animal studies suggest that clofibrate interrupts cholesterol biosynthesis prior to mevalonate formation.

Mechanism of action

Clofibrate increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. 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. Clofibrate also inhibits the synthesis and increases the clearance of apolipoprotein B, a carrier molecule for VLDL. Also, as a fibrate, Clofibrate is an agonist of the PPAR-α receptor[4] in muscle, liver, and other tissues. This agonism ultimately leads to modification in gene expression resulting in increased beta-oxidation, decreased triglyceride secretion, increased HDL, increased lipoprotein lipase activity.

TargetActionsOrganism
APeroxisome proliferator-activated receptor alpha
agonist
Humans
Absorption

Completely but slowly absorbed from the intestine. Between 95% and 99% of an oral dose of clofibrate is excreted in the urine as free and conjugated clofibric acid; thus, the absorption of clofibrate is virtually complete.

Volume of distribution

Not Available

Protein binding

Highly protein-bound (95% to 97%).

Metabolism

Hepatic and gastrointestinal: rapid de-esterification occurs in the gastrointestinal tract and/or on first-pass metabolism to produce the active form, clofibric acid (chlorophenoxy isobutyric acid [CPIB]).

Route of elimination

Not Available

Half-life

Half-life in normal volunteers averages 18 to 22 hours (range 14 to 35 hours) but can vary by up to 7 hours in the same subject at different times.

Clearance

Not Available

Adverse Effects
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Toxicity

Oral, mouse: LD50 = 1220 mg/kg; Oral, rabbit: LD50 = 1370 mg/kg; Oral, rat: LD50 = 940 mg/kg. No reported case of overdosage in humans.

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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbametapirThe serum concentration of Clofibrate can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Clofibrate.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Clofibrate.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Clofibrate.
AcetaminophenClofibrate may increase the hepatotoxic activities of Acetaminophen.
Food Interactions
  • Take with food. Food decreases the risk of GI side effects.

Products

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International/Other Brands
Alufibrate (The Central) / Atromid-S / Binograc (Kotobuki Seiyaku) / Clobrate (Johnson) / ELPI / Hisunsero (Newai Chem) / Koliva (Golden Horse) / Lipofacton / Myanlin (Sinton)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Atromid S Cap 500mgCapsule500 mg / capOralAyerst Laboratories1968-12-311997-08-15Canada flag
Atromid-S 1gmCapsule1 g / capOralWyeth Ayerst Canada Inc.1994-12-311998-10-20Canada flag
Atromid-S Cap 500mgCapsule500 mg / capOralWyeth Ayerst Canada Inc.1996-10-252000-08-02Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Novo-fibrate Cap 500mgCapsule500 mg / capOralNovopharm Limited1976-12-312005-08-10Canada flag

Categories

ATC Codes
C10AB01 — Clofibrate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenoxyacetic acid derivatives
Direct Parent
Phenoxyacetic acid derivatives
Alternative Parents
Phenoxy compounds / Phenol ethers / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organochlorides / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Alkyl aryl ether / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Chlorobenzene / Ether / Halobenzene
show 10 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
ethyl ester, aromatic ether, monochlorobenzenes (CHEBI:3750)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
HPN91K7FU3
CAS number
637-07-0
InChI Key
KNHUKKLJHYUCFP-UHFFFAOYSA-N
InChI
InChI=1S/C12H15ClO3/c1-4-15-11(14)12(2,3)16-10-7-5-9(13)6-8-10/h5-8H,4H2,1-3H3
IUPAC Name
ethyl 2-(4-chlorophenoxy)-2-methylpropanoate
SMILES
CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1

References

Synthesis Reference

Jones, W.G.M.,Thorp, J.M. and Waring, W.S.; U.S. Patent 3,262,850; July 26, 1966; assigned to Imperial Chemical Industries Limited, England.

General References
Not Available
Human Metabolome Database
HMDB0014774
KEGG Drug
D00279
KEGG Compound
C06916
PubChem Compound
2796
PubChem Substance
46504748
ChemSpider
2694
BindingDB
50085047
RxNav
2594
ChEBI
3750
ChEMBL
CHEMBL565
ZINC
ZINC000000056648
Therapeutic Targets Database
DAP000262
PharmGKB
PA449045
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Clofibrate
MSDS
Download (62.6 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Myocardial Infarction / Myocardial Ischemia1
Not AvailableCompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Myocardial Infarction / Myocardial Ischemia1

Pharmacoeconomics

Manufacturers
  • Wyeth ayerst laboratories
  • Banner pharmacaps inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Watson laboratories inc
Packagers
  • Banner Pharmacaps Inc.
  • Major Pharmaceuticals
  • Novopharm Ltd.
Dosage Forms
FormRouteStrength
CapsuleOral1 g / cap
CapsuleOral
CapsuleOral500 mg / cap
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)118-119Jones, W.G.M.,Thorp, J.M. and Waring, W.S.; U.S. Patent 3,262,850; July 26, 1966; assigned to Imperial Chemical Industries Limited, England.
boiling point (°C)149 °C at 2.00E+01 mm HgPhysProp
water solubilityInsolubleNot Available
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.029 mg/mLALOGPS
logP3.99ALOGPS
logP3.4Chemaxon
logS-3.9ALOGPS
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area35.53 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity62.14 m3·mol-1Chemaxon
Polarizability24.7 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9329
Caco-2 permeable+0.717
P-glycoprotein substrateNon-substrate0.589
P-glycoprotein inhibitor INon-inhibitor0.7133
P-glycoprotein inhibitor IINon-inhibitor0.8544
Renal organic cation transporterNon-inhibitor0.8868
CYP450 2C9 substrateNon-substrate0.8517
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6692
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8861
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5832
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.5492
BiodegradationNot ready biodegradable0.9711
Rat acute toxicity2.3806 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9891
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.78 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00or-4900000000-b0f27a4473b7e59d68c3
Mass Spectrum (Electron Ionization)MSsplash10-004i-3900000000-fc2f01df51d424557e9f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9220000000-8e4c6bb9fc22e3503092
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-5920000000-156beedffe1cc1f8b11f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001r-9200000000-c6073e93908134e14d68
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0096-9300000000-0f7a08357c01d04dff59
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0040-9400000000-4a078011a70c39921f1a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9200000000-67240ceb48f7fd0c3aa0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-154.3778988
predicted
DarkChem Lite v0.1.0
[M-H]-154.5927988
predicted
DarkChem Lite v0.1.0
[M-H]-153.29771
predicted
DeepCCS 1.0 (2019)
[M+H]+155.4228988
predicted
DarkChem Lite v0.1.0
[M+H]+155.1726988
predicted
DarkChem Lite v0.1.0
[M+H]+155.65572
predicted
DeepCCS 1.0 (2019)
[M+Na]+154.8313988
predicted
DarkChem Lite v0.1.0
[M+Na]+155.0638988
predicted
DarkChem Lite v0.1.0
[M+Na]+161.74886
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Peroxisome proliferator-activated receptor alpha
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
  1. Barclay TB, Peters JM, Sewer MB, Ferrari L, Gonzalez FJ, Morgan ET: Modulation of cytochrome P-450 gene expression in endotoxemic mice is tissue specific and peroxisome proliferator-activated receptor-alpha dependent. J Pharmacol Exp Ther. 1999 Sep;290(3):1250-7. [Article]
  2. Murata M, Kaji H, Takahashi Y, Iida K, Mizuno I, Okimura Y, Abe H, Chihara K: Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro. Biochem Biophys Res Commun. 2000 Apr 13;270(2):343-8. [Article]
  3. Hunt MC, Lindquist PJ, Peters JM, Gonzalez FJ, Diczfalusy U, Alexson SE: Involvement of the peroxisome proliferator-activated receptor alpha in regulating long-chain acyl-CoA thioesterases. J Lipid Res. 2000 May;41(5):814-23. [Article]
  4. Casas F, Domenjoud L, Rochard P, Hatier R, Rodier A, Daury L, Bianchi A, Kremarik-Bouillaud P, Becuwe P, Keller J, Schohn H, Wrutniak-Cabello C, Cabello G, Dauca M: A 45 kDa protein related to PPARgamma2, induced by peroxisome proliferators, is located in the mitochondrial matrix. FEBS Lett. 2000 Jul 28;478(1-2):4-8. [Article]
  5. Komuves LG, Hanley K, Lefebvre AM, Man MQ, Ng DC, Bikle DD, Williams ML, Elias PM, Auwerx J, Feingold KR: Stimulation of PPARalpha promotes epidermal keratinocyte differentiation in vivo. J Invest Dermatol. 2000 Sep;115(3):353-60. [Article]
  6. Gelosa P, Banfi C, Gianella A, Brioschi M, Pignieri A, Nobili E, Castiglioni L, Cimino M, Tremoli E, Sironi L: Peroxisome proliferator-activated receptor {alpha} agonism prevents renal damage and the oxidative stress and inflammatory processes affecting the brains of stroke-prone rats. J Pharmacol Exp Ther. 2010 Nov;335(2):324-31. doi: 10.1124/jpet.110.171090. Epub 2010 Jul 29. [Article]
  7. Palkar PS, Anderson CR, Ferry CH, Gonzalez FJ, Peters JM: Effect of prenatal peroxisome proliferator-activated receptor alpha (PPARalpha) agonism on postnatal development. Toxicology. 2010 Sep 30;276(1):79-84. doi: 10.1016/j.tox.2010.07.008. Epub 2010 Jul 15. [Article]

Enzymes

Details1. Cytochrome P450 1A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d 24-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
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Lee PC, Marquardt M, Lech JJ: Metabolism of nonylphenol by rat and human microsomes. Toxicol Lett. 1998 Oct 15;99(2):117-26. doi: 10.1016/s0378-4274(98)00153-2. [Article]
  2. Seree E, Villard PH, Pascussi JM, Pineau T, Maurel P, Nguyen QB, Fallone F, Martin PM, Champion S, Lacarelle B, Savouret JF, Barra Y: Evidence for a new human CYP1A1 regulation pathway involving PPAR-alpha and 2 PPRE sites. Gastroenterology. 2004 Nov;127(5):1436-45. doi: 10.1053/j.gastro.2004.08.023. [Article]
  3. Rey-Grobellet X, Eeckhoutte C, Sutra JF, Alvinerie M, Galtier P: Major involvement of rabbit liver cytochrome P4501A in thiabendazole 5-hydroxylation. Xenobiotica. 1996 Jul;26(7):765-78. [Article]
Details2. Cytochrome P450 4A11
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Leukotriene-b4 20-monooxygenase activity
Specific Function
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 2...
Gene Name
CYP4A11
Uniprot ID
Q02928
Uniprot Name
Cytochrome P450 4A11
Molecular Weight
59347.31 Da
References
  1. Li J, Li D, Tie C, Wu J, Wu Q, Li Q: Cisplatin-mediated cytotoxicity through inducing CYP4A 11 expression in human renal tubular epithelial cells. J Toxicol Sci. 2015 Dec;40(6):895-900. doi: 10.2131/jts.40.895. [Article]
  2. Raucy JL, Lasker J, Ozaki K, Zoleta V: Regulation of CYP2E1 by ethanol and palmitic acid and CYP4A11 by clofibrate in primary cultures of human hepatocytes. Toxicol Sci. 2004 Jun;79(2):233-41. doi: 10.1093/toxsci/kfh126. Epub 2004 Mar 31. [Article]
  3. Savas U, Machemer DE, Hsu MH, Gaynor P, Lasker JM, Tukey RH, Johnson EF: Opposing roles of peroxisome proliferator-activated receptor alpha and growth hormone in the regulation of CYP4A11 expression in a transgenic mouse model. J Biol Chem. 2009 Jun 12;284(24):16541-52. doi: 10.1074/jbc.M902074200. Epub 2009 Apr 14. [Article]
Details3. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
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. Donato MT, Castell JV, Gomez-Lechon MJ: Effect of model inducers on cytochrome P450 activities of human hepatocytes in primary culture. Drug Metab Dispos. 1995 May;23(5):553-8. [Article]
  2. 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]
Details4. Glutathione S-transferase A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA2
Uniprot ID
P09210
Uniprot Name
Glutathione S-transferase A2
Molecular Weight
25663.675 Da
References
  1. Foliot A, Touchard D, Mallet L: Inhibition of liver glutathione S-transferase activity in rats by hypolipidemic drugs related or unrelated to clofibrate. Biochem Pharmacol. 1986 May 15;35(10):1685-90. [Article]
  2. Foliot A, Touchard D, Celier C: Impairment of hepatic glutathione S-transferase activity as a cause of reduced biliary sulfobromophthalein excretion in clofibrate-treated rats. Biochem Pharmacol. 1984 Sep 15;33(18):2829-34. [Article]
Details5. Cytochrome P450 2E1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Lee PC, Marquardt M, Lech JJ: Metabolism of nonylphenol by rat and human microsomes. Toxicol Lett. 1998 Oct 15;99(2):117-26. doi: 10.1016/s0378-4274(98)00153-2. [Article]
  2. Adas F, Berthou F, Picart D, Lozac'h P, Beauge F, Amet Y: Involvement of cytochrome P450 2E1 in the (omega-1)-hydroxylation of oleic acid in human and rat liver microsomes. J Lipid Res. 1998 Jun;39(6):1210-9. [Article]

Carriers

Details1. Thyroxine-binding globulin
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Serine-type endopeptidase inhibitor activity
Specific Function
Major thyroid hormone transport protein in serum.
Gene Name
SERPINA7
Uniprot ID
P05543
Uniprot Name
Thyroxine-binding globulin
Molecular Weight
46324.12 Da
References
  1. CYTOMEL (liothyronine) FDA label [File]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:53