CIPROFIBRATE

Possibly Marketed Outside US

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

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 2752		58.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperlipidemia 82 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 8583	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.

C_max

Value	Dose	Analyte	Population
66 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8831918/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
111 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8831918/	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
20.93 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21763220/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
24 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
22 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
17 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1666 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8831918/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2832 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8831918/	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
818.58 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21763220/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1370 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1759 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2445 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2431 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
104 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8831918/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8831918/	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
81 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
117 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
172 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
154 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2611089/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFIBRATE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% OTHER GOV'T https://www.medicines.org.uk/emc/product/4997/smpc#PHARMACOKINETIC_PROPS			CIPROFIBRATE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/	Disc. AE: Alopecia, Somnolence... AEs leading to discontinuation/dose reduction: Alopecia (1.2%) Somnolence (1.2%) Fever (1.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/

AEs

AE	Significance	Dose	Population
Alopecia	1.2% Disc. AE	100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/
Fever	1.2% Disc. AE	100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/
Somnolence	1.2% Disc. AE	100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9015467/

PubMed

Title	Date	PubMed
Characterization of liver function in transdifferentiated hepatocytes.	2006-01	15965953
Ciprofibrate stimulates the gastrin-producing cell by acting luminally on antral PPAR-alpha.	2005-12	16099866
Gene expression profiling of the PPAR-alpha agonist ciprofibrate in the cynomolgus monkey liver.	2005-11	16081524
The effect of ciprofibrate on flow-mediated dilation and inflammatory markers in patients with combined hyperlipidemia.	2005-09-16	16162440
Monocyte release of tumor necrosis factor-alpha and interleukin-1beta in primary type IIa and IIb dyslipidemic patients treated with statins or fibrates.	2005-09	16116345
Regulation of mouse organic anion-transporting polypeptides (Oatps) in liver by prototypical microsomal enzyme inducers that activate distinct transcription factor pathways.	2005-09	15919853
Agonists for the peroxisome proliferator-activated receptor-alpha and the retinoid X receptor inhibit inflammatory responses of microglia.	2005-08-01	15968640
Induction of the multidrug resistance-associated protein family of transporters by chemical activators of receptor-mediated pathways in mouse liver.	2005-07	15833929
[A case of Parkinsonian syndrome, cognitive impairment and hyperammonemia induced by divalproate sodium prescribed for bipolar disorder].	2005-06-24	15971646
Induction of pancreatic acinar cell proliferation by thyroid hormone.	2005-06	15930165
Differences in cell proliferation in rodent and human hepatic derived cell lines exposed to ciprofibrate.	2005-05-26	15863271
Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters.	2005-05-04	15853379
Study of the liquid chromatography retention of some fibrate-type antihyperlipidemic drugs on C18 and CN columns: application for quantitation in pharmaceutical formulations.	2005-04-30	15859075
Regulation of human hepatic hydroxysteroid sulfotransferase gene expression by the peroxisome proliferator-activated receptor alpha transcription factor.	2005-04	15635043
Application of comparative functional genomics to identify best-fit mouse models to study human cancer.	2004-12	15565109
Plasmalogens in rat liver chromatin: new molecules involved in cell proliferation.	2004-12	15389549
The levels of soluble adhesion molecules in diabetic and nondiabetic patients with combined hyperlipoproteinemia and the effect of ciprofibrate therapy.	2004-11-18	15547649
Peroxisome proliferator-activated receptors as regulators of lipid metabolism; tissue differential expression in adipose tissues during cold acclimatization and hibernation of jerboa (Jaculus orientalis).	2004-11	15589684
Activation of peroxisome proliferator-activated receptor alpha in rat spinal cord after peripheral noxious stimulation.	2004-10-07	15380308
The effect of statins and fibrates on interferon-gamma and interleukin-2 release in patients with primary type II dyslipidemia.	2004-10	15380456
Fenofibrate impairs rat mitochondrial function by inhibition of respiratory complex I.	2004-10	15166256
Fibrates induce hepatic peroxisome and mitochondrial proliferation without overt evidence of cellular proliferation and oxidative stress in cynomolgus monkeys.	2004-09	15131011
Effects of vitamin E on the NF-kappaB pathway in rats treated with the peroxisome proliferator, ciprofibrate.	2004-08-15	15289085
PPARalpha agonists stimulate progastrin production in human colorectal carcinoma cells.	2004-08-15	15177943
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).	2004-07-23	15272932
Application of UV-derivative spectra for determination of four antihyperlipidaemic drugs in pharmaceutical formulations.	2004-07-21	15259852
Effects of peroxisome proliferator-activated receptor alpha activation on pathways contributing to cholesterol homeostasis in rat hepatocytes.	2004-07-05	15238219
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.	2004-07-02	15123680
Peroxisome proliferator activated receptors alpha and gamma require zinc for their anti-inflammatory properties in porcine vascular endothelial cells.	2004-07	15226458
Visualization and quantitation of peroxisomes using fluorescent nanocrystals: treatment of rats and monkeys with fibrates and detection in the liver.	2004-07	15084755
Miniaturized fluorescent RNA dot blot method for rapid quantitation of gene expression.	2004-06-10	15191615
Effects of antihypertensive and hypolipidemic drugs on plasma and high-density lipoprotein-associated platelet activating factor-acetylhydrolase activity.	2004-06	15309245
Homocysteine and reactive oxygen species in metabolic syndrome, type 2 diabetes mellitus, and atheroscleropathy: the pleiotropic effects of folate supplementation.	2004-05-10	15134582
Peroxisome proliferator-activated receptor alpha agonists as therapy for autoimmune disease.	2004-05-01	15100326
Characterization of the species-specificity of peroxisome proliferators in rat and human hepatocytes.	2004-04	14976357
Peroxisome proliferator-activated receptor alpha (PPARalpha) activators induce hepatic farnesyl diphosphate synthase gene expression in rodents.	2004-02	15084352
Overexpression of SR-BI by adenoviral vector reverses the fibrateinduced hypercholesterolemia of apolipoprotein E-deficient mice.	2003-12-26	14570884
Hypertriglyceridemia increases mitochondrial resting respiration and susceptibility to permeability transition.	2003-10	14740893
Cell proliferation and apoptosis are altered in mice deficient in the NF-kappaB p50 subunit after treatment with the peroxisome proliferator ciprofibrate.	2003-10	12883078
Hibernation impact on the catalytic activities of the mitochondrial D-3-hydroxybutyrate dehydrogenase in liver and brain tissues of jerboa (Jaculus orientalis).	2003-09-10	12964952
[Long-term hypolipidemic treatment of mixed hyperlipidemia with a combination of statins and fibrates].	2003-08	14626567
Action of ciprofibrate in type IIb hyperlipoproteinemia: modulation of the atherogenic lipoprotein phenotype and stimulation of high-density lipoprotein-mediated cellular cholesterol efflux.	2003-08	12915663
Lipid-lowering drugs and serum liver enzymes: the effects of body weight and baseline enzyme levels.	2003-08	12914553
[Efficacy and safety of combined statin-fenofibrates therapy compared with monotherapy in patients with mixed hyperlipidemia and high risk of coronary heart disease].	2003-07	14593958
Changes of peroxisomal fatty acid metabolism during cold acclimatization in hibernating jerboa (Jaculus orientalis).	2003-07	14505827
LDL-cholesterol, HDL-cholesterol or triglycerides--which is the culprit?	2003-07	12880691
Fibrates and renal function.	2003-07	12872864
[Ciprofibrate-induced acute cholestatic hepatitis].	2003-06	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.	2003-06	12877356
Plasma levels of HGF in rats treated with tumor promoters.	1992-01	1370768

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

Name

Type

Language

NSC-759617

Preferred Name

English

CIPROFIBRATE

Official Name

English

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

Common Name

English

CIPROFIBRATE [EP MONOGRAPH]

Common Name

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