CIPROFIBRATE

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 Search

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

Molecular Formula	C13H14Cl2O3
Molecular Weight	289.154
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/454514
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12163133 | https://www.ncbi.nlm.nih.gov/pubmed/8497456 | https://www.ncbi.nlm.nih.gov/pubmed/15272932 |https://www.ncbi.nlm.nih.gov/pubmed/8831920

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12163133	Agonist 2678		58.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperlipidemia 80 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8497456 https://www.ncbi.nlm.nih.gov/pubmed/8831920 https://www.ncbi.nlm.nih.gov/pubmed/8831912 https://www.ncbi.nlm.nih.gov/pubmed/15272932	Primary		Approved 8429	CIPROFIBRATE Approved Use Ciprofibrate tablets are indicated as an adjunct to diet and other non-pharmacological treatment (e.g. exercise, weight reduction) for the following: - Treatment of severe hypertriglyceridaemia with or without low HDL cholesterol. - Mixed hyperlipidaemia when a statin is contraindicated or not tolerated.

PubMed

Title	Date	PubMed
Plasma levels of HGF in rats treated with tumor promoters.	1992 Jan	1370768
[Long-term hypolipidemic treatment of mixed hyperlipidemia with a combination of statins and fibrates].	2003 Aug	14626567
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	12915663
Lipid-lowering drugs and serum liver enzymes: the effects of body weight and baseline enzyme levels.	2003 Aug	12914553
Overexpression of SR-BI by adenoviral vector reverses the fibrateinduced hypercholesterolemia of apolipoprotein E-deficient mice.	2003 Dec 26	14570884
[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	14593958
Changes of peroxisomal fatty acid metabolism during cold acclimatization in hibernating jerboa (Jaculus orientalis).	2003 Jul	14505827
LDL-cholesterol, HDL-cholesterol or triglycerides--which is the culprit?	2003 Jul	12880691
Fibrates and renal function.	2003 Jul	12872864
[Ciprofibrate-induced acute cholestatic hepatitis].	2003 Jun	12910067
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	12877356
Hypertriglyceridemia increases mitochondrial resting respiration and susceptibility to permeability transition.	2003 Oct	14740893
Cell proliferation and apoptosis are altered in mice deficient in the NF-kappaB p50 subunit after treatment with the peroxisome proliferator ciprofibrate.	2003 Oct	12883078
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	12964952
Characterization of the species-specificity of peroxisome proliferators in rat and human hepatocytes.	2004 Apr	14976357
Effects of vitamin E on the NF-kappaB pathway in rats treated with the peroxisome proliferator, ciprofibrate.	2004 Aug 15	15289085
PPARalpha agonists stimulate progastrin production in human colorectal carcinoma cells.	2004 Aug 15	15177943
Application of comparative functional genomics to identify best-fit mouse models to study human cancer.	2004 Dec	15565109
Plasmalogens in rat liver chromatin: new molecules involved in cell proliferation.	2004 Dec	15389549
Peroxisome proliferator-activated receptor alpha (PPARalpha) activators induce hepatic farnesyl diphosphate synthase gene expression in rodents.	2004 Feb	15084352
Application of UV-derivative spectra for determination of four antihyperlipidaemic drugs in pharmaceutical formulations.	2004 Jan-Feb	15259852
Peroxisome proliferator activated receptors alpha and gamma require zinc for their anti-inflammatory properties in porcine vascular endothelial cells.	2004 Jul	15226458
Visualization and quantitation of peroxisomes using fluorescent nanocrystals: treatment of rats and monkeys with fibrates and detection in the liver.	2004 Jul	15084755
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	15123680
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	15272932
Effects of peroxisome proliferator-activated receptor alpha activation on pathways contributing to cholesterol homeostasis in rat hepatocytes.	2004 Jul 5	15238219
Effects of antihypertensive and hypolipidemic drugs on plasma and high-density lipoprotein-associated platelet activating factor-acetylhydrolase activity.	2004 Jun	15309245
Miniaturized fluorescent RNA dot blot method for rapid quantitation of gene expression.	2004 Jun 10	15191615
Peroxisome proliferator-activated receptor alpha agonists as therapy for autoimmune disease.	2004 May 1	15100326
Homocysteine and reactive oxygen species in metabolic syndrome, type 2 diabetes mellitus, and atheroscleropathy: the pleiotropic effects of folate supplementation.	2004 May 10	15134582
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	15589684
The levels of soluble adhesion molecules in diabetic and nondiabetic patients with combined hyperlipoproteinemia and the effect of ciprofibrate therapy.	2004 Nov-Dec	15547649
The effect of statins and fibrates on interferon-gamma and interleukin-2 release in patients with primary type II dyslipidemia.	2004 Oct	15380456
Fenofibrate impairs rat mitochondrial function by inhibition of respiratory complex I.	2004 Oct	15166256
Activation of peroxisome proliferator-activated receptor alpha in rat spinal cord after peripheral noxious stimulation.	2004 Oct 7	15380308
Fibrates induce hepatic peroxisome and mitochondrial proliferation without overt evidence of cellular proliferation and oxidative stress in cynomolgus monkeys.	2004 Sep	15131011
Regulation of human hepatic hydroxysteroid sulfotransferase gene expression by the peroxisome proliferator-activated receptor alpha transcription factor.	2005 Apr	15635043
Agonists for the peroxisome proliferator-activated receptor-alpha and the retinoid X receptor inhibit inflammatory responses of microglia.	2005 Aug 1	15968640
Ciprofibrate stimulates the gastrin-producing cell by acting luminally on antral PPAR-alpha.	2005 Dec	16099866
[A case of Parkinsonian syndrome, cognitive impairment and hyperammonemia induced by divalproate sodium prescribed for bipolar disorder].	2005 Jan-Feb	15971646
Induction of the multidrug resistance-associated protein family of transporters by chemical activators of receptor-mediated pathways in mouse liver.	2005 Jul	15833929
The effect of ciprofibrate on flow-mediated dilation and inflammatory markers in patients with combined hyperlipidemia.	2005 Jul-Aug	16162440
Induction of pancreatic acinar cell proliferation by thyroid hormone.	2005 Jun	15930165
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	15859075
Differences in cell proliferation in rodent and human hepatic derived cell lines exposed to ciprofibrate.	2005 May 26	15863271
Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters.	2005 May 4	15853379
Gene expression profiling of the PPAR-alpha agonist ciprofibrate in the cynomolgus monkey liver.	2005 Nov	16081524
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	16116345
Regulation of mouse organic anion-transporting polypeptides (Oatps) in liver by prototypical microsomal enzyme inducers that activate distinct transcription factor pathways.	2005 Sep	15919853
Characterization of liver function in transdifferentiated hepatocytes.	2006 Jan	15965953

Patents

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:57:57 GMT 2023` Edited by `admin` on `Sat Dec 16 16:57:57 GMT 2023`
Record UNII	F8252JGO9S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIPROFIBRATE

Official Name

English

PROPANOIC ACID, 2-(4-(2,2-DICHLOROCYCLOPROPYL)PHENOXY)-2-METHYL-

Common Name

English

CIPROFIBRATE [EP MONOGRAPH]

Common Name

English

NSC-759617

Code

English

CIPROFIBRATE [USAN]

Common Name

English

CIPROFIBRATE [MART.]

Common Name

English

CIPROFIBRATE [MI]

Common Name

English

2-(P-(2,2-DICHLOROCYCLOPROPYL)PHENOXY)-2-METHYLPROPIONIC ACID

Common Name

English

WIN-35833

Code

English

WIN 35833

Code

English

Ciprofibrate [WHO-DD]

Common Name

English

ciprofibrate [INN]

Common Name

English

CIPROFIBRATE [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QC10AB08