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Details

Stereochemistry RACEMIC
Molecular Formula C13H14Cl2O3
Molecular Weight 289.154
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIPROFIBRATE

SMILES

CC(C)(OC1=CC=C(C=C1)C2CC2(Cl)Cl)C(O)=O

InChI

InChIKey=KPSRODZRAIWAKH-UHFFFAOYSA-N
InChI=1S/C13H14Cl2O3/c1-12(2,11(16)17)18-9-5-3-8(4-6-9)10-7-13(10,14)15/h3-6,10H,7H2,1-2H3,(H,16,17)

HIDE SMILES / InChI

Description

Ciprofibrate is an orally active phenoxyisobutyrate hypolipidemic compound. It acts by activating peroxisome proliferator activated receptor alpha. Ciprofibrate is efficacious for the correction of hyperlipidaemias.

CNS Activity

Originator

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
58.0 µM [Ki]
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
CIPROFIBRATE
PMID

PMID

TitleDatePMID
Plasma levels of HGF in rats treated with tumor promoters.
1992 Jan
[Long-term hypolipidemic treatment of mixed hyperlipidemia with a combination of statins and fibrates].
2003 Aug
Action of ciprofibrate in type IIb hyperlipoproteinemia: modulation of the atherogenic lipoprotein phenotype and stimulation of high-density lipoprotein-mediated cellular cholesterol efflux.
2003 Aug
Lipid-lowering drugs and serum liver enzymes: the effects of body weight and baseline enzyme levels.
2003 Aug
Overexpression of SR-BI by adenoviral vector reverses the fibrateinduced hypercholesterolemia of apolipoprotein E-deficient mice.
2003 Dec 26
[Efficacy and safety of combined statin-fenofibrates therapy compared with monotherapy in patients with mixed hyperlipidemia and high risk of coronary heart disease].
2003 Jul
Changes of peroxisomal fatty acid metabolism during cold acclimatization in hibernating jerboa (Jaculus orientalis).
2003 Jul
LDL-cholesterol, HDL-cholesterol or triglycerides--which is the culprit?
2003 Jul
Fibrates and renal function.
2003 Jul
[Ciprofibrate-induced acute cholestatic hepatitis].
2003 Jun
Fibrates and their newly synthesized glycinate or glycinate-methylester derivatives: comparison of the interactions with liver cytochrome P450 dependent monooxygenase- and oxidase-functions in vitro.
2003 Jun
Hypertriglyceridemia increases mitochondrial resting respiration and susceptibility to permeability transition.
2003 Oct
Cell proliferation and apoptosis are altered in mice deficient in the NF-kappaB p50 subunit after treatment with the peroxisome proliferator ciprofibrate.
2003 Oct
Hibernation impact on the catalytic activities of the mitochondrial D-3-hydroxybutyrate dehydrogenase in liver and brain tissues of jerboa (Jaculus orientalis).
2003 Sep 10
Characterization of the species-specificity of peroxisome proliferators in rat and human hepatocytes.
2004 Apr
Effects of vitamin E on the NF-kappaB pathway in rats treated with the peroxisome proliferator, ciprofibrate.
2004 Aug 15
PPARalpha agonists stimulate progastrin production in human colorectal carcinoma cells.
2004 Aug 15
Application of comparative functional genomics to identify best-fit mouse models to study human cancer.
2004 Dec
Plasmalogens in rat liver chromatin: new molecules involved in cell proliferation.
2004 Dec
Peroxisome proliferator-activated receptor alpha (PPARalpha) activators induce hepatic farnesyl diphosphate synthase gene expression in rodents.
2004 Feb
Application of UV-derivative spectra for determination of four antihyperlipidaemic drugs in pharmaceutical formulations.
2004 Jan-Feb
Peroxisome proliferator activated receptors alpha and gamma require zinc for their anti-inflammatory properties in porcine vascular endothelial cells.
2004 Jul
Visualization and quantitation of peroxisomes using fluorescent nanocrystals: treatment of rats and monkeys with fibrates and detection in the liver.
2004 Jul
The peroxisome proliferator-activated receptor alpha (PPARalpha) agonist ciprofibrate inhibits apolipoprotein B mRNA editing in low density lipoprotein receptor-deficient mice: effects on plasma lipoproteins and the development of atherosclerotic lesions.
2004 Jul 2
Ciprofibrate therapy in patients with hypertriglyceridemia and low high density lipoprotein (HDL)-cholesterol: greater reduction of non-HDL cholesterol in subjects with excess body weight (The CIPROAMLAT study).
2004 Jul 23
Effects of peroxisome proliferator-activated receptor alpha activation on pathways contributing to cholesterol homeostasis in rat hepatocytes.
2004 Jul 5
Effects of antihypertensive and hypolipidemic drugs on plasma and high-density lipoprotein-associated platelet activating factor-acetylhydrolase activity.
2004 Jun
Miniaturized fluorescent RNA dot blot method for rapid quantitation of gene expression.
2004 Jun 10
Peroxisome proliferator-activated receptor alpha agonists as therapy for autoimmune disease.
2004 May 1
Homocysteine and reactive oxygen species in metabolic syndrome, type 2 diabetes mellitus, and atheroscleropathy: the pleiotropic effects of folate supplementation.
2004 May 10
Peroxisome proliferator-activated receptors as regulators of lipid metabolism; tissue differential expression in adipose tissues during cold acclimatization and hibernation of jerboa (Jaculus orientalis).
2004 Nov
The levels of soluble adhesion molecules in diabetic and nondiabetic patients with combined hyperlipoproteinemia and the effect of ciprofibrate therapy.
2004 Nov-Dec
The effect of statins and fibrates on interferon-gamma and interleukin-2 release in patients with primary type II dyslipidemia.
2004 Oct
Fenofibrate impairs rat mitochondrial function by inhibition of respiratory complex I.
2004 Oct
Activation of peroxisome proliferator-activated receptor alpha in rat spinal cord after peripheral noxious stimulation.
2004 Oct 7
Fibrates induce hepatic peroxisome and mitochondrial proliferation without overt evidence of cellular proliferation and oxidative stress in cynomolgus monkeys.
2004 Sep
Regulation of human hepatic hydroxysteroid sulfotransferase gene expression by the peroxisome proliferator-activated receptor alpha transcription factor.
2005 Apr
Agonists for the peroxisome proliferator-activated receptor-alpha and the retinoid X receptor inhibit inflammatory responses of microglia.
2005 Aug 1
Ciprofibrate stimulates the gastrin-producing cell by acting luminally on antral PPAR-alpha.
2005 Dec
[A case of Parkinsonian syndrome, cognitive impairment and hyperammonemia induced by divalproate sodium prescribed for bipolar disorder].
2005 Jan-Feb
Induction of the multidrug resistance-associated protein family of transporters by chemical activators of receptor-mediated pathways in mouse liver.
2005 Jul
The effect of ciprofibrate on flow-mediated dilation and inflammatory markers in patients with combined hyperlipidemia.
2005 Jul-Aug
Induction of pancreatic acinar cell proliferation by thyroid hormone.
2005 Jun
Study of the liquid chromatography retention of some fibrate-type antihyperlipidemic drugs on C18 and CN columns: application for quantitation in pharmaceutical formulations.
2005 Mar-Apr
Differences in cell proliferation in rodent and human hepatic derived cell lines exposed to ciprofibrate.
2005 May 26
Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters.
2005 May 4
Gene expression profiling of the PPAR-alpha agonist ciprofibrate in the cynomolgus monkey liver.
2005 Nov
Monocyte release of tumor necrosis factor-alpha and interleukin-1beta in primary type IIa and IIb dyslipidemic patients treated with statins or fibrates.
2005 Sep
Regulation of mouse organic anion-transporting polypeptides (Oatps) in liver by prototypical microsomal enzyme inducers that activate distinct transcription factor pathways.
2005 Sep
Characterization of liver function in transdifferentiated hepatocytes.
2006 Jan
Patent

Sample Use Guides

In Vivo Use Guide
The recommended dosage is one tablet (100mg ciprofibrate) per day.
Route of Administration: Oral
In Vitro Use Guide
0.25 mM ciprofibrate was found to increase the phosphorylation of epidermal-growth-factor receptor in isolated rat hepatocytes
Name Type Language
CIPROFIBRATE
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
PROPANOIC ACID, 2-(4-(2,2-DICHLOROCYCLOPROPYL)PHENOXY)-2-METHYL-
Common Name English
CIPROFIBRATE [USAN]
Common Name English
CIPROFIBRATE [MART.]
Common Name English
CIPROFIBRATE [MI]
Common Name English
CIPROFIBRATE [WHO-DD]
Common Name English
2-(P-(2,2-DICHLOROCYCLOPROPYL)PHENOXY)-2-METHYLPROPIONIC ACID
Common Name English
WIN-35833
Code English
WIN 35833
Code English
CIPROFIBRATE [INN]
Common Name English
CIPROFIBRATE [EP]
Common Name English
Classification Tree Code System Code
WHO-VATC QC10AB08
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
WHO-ATC C10AB08
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
Code System Code Type Description
CAS
52214-84-3
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
PUBCHEM
2763
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY SWITZERF
NCI_THESAURUS
C87471
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
WIKIPEDIA
CIPROFIBRATE
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
ChEMBL
CHEMBL557555
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
MESH
C019304
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
ECHA (EC/EINECS)
257-744-6
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
MERCK INDEX
M3582
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY Merck Index
EPA CompTox
52214-84-3
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
EVMPD
SUB07469MIG
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY
RXCUI
21149
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY RxNorm
INN
4057
Created by admin on Tue Mar 06 12:21:56 UTC 2018 , Edited by admin on Tue Mar 06 12:21:56 UTC 2018
PRIMARY