Ciprofibrate Chemical Properties

Melting point:

114-116°

Boiling point:

401.74°C (rough estimate)

Density 

1.2576 (rough estimate)

refractive index 

1.5209 (estimate)

storage temp. 

2-8°C

solubility 

Practically insoluble in water, freely soluble in anhydrous ethanol, soluble in toluene.

pka

3.31±0.10(Predicted)

form 

Solid

color 

White to Pale Beige

Merck 

14,2313

InChIKey

KPSRODZRAIWAKH-UHFFFAOYSA-N

CAS DataBase Reference

52214-84-3(CAS DataBase Reference)

EPA Substance Registry System

Propanoic acid, 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methyl- (52214-84-3)

Safety Information

Hazard Codes 

T

Risk Statements 

45

Safety Statements 

53-22-36/37/39-45

WGK Germany 

3

RTECS 

UF0880000

HS Code 

29189900

MSDS

• Language:English Provider:Ciprofibrate
• Language:English Provider:SigmaAldrich

Ciprofibrate Usage And Synthesis

Description

Ciprofibrate is a potent, long-acting hypolipidemic agent related to clofibrate, bezafibrate and fenofibrate. It is effective in types IIa, IIb, IIX and IV hyperlipoproteinemias, and produces a beneficial elevation of the anti-atherogenic HDL.

Description

Ciprofibrate is an agonist of peroxisome proliferator-activated receptor α (PPARα; EC₅₀ = 0.9 μM in a transactivation assay). It is selective for PPARα over PPARγ and PPARδ at 300 μM. Ciprofibrate (250 μM) induces cell cycle arrest at the G₂/M and S phases in Fao rat, but not HepG2 human, hepatocellular carcinoma cells. It decreases fasting plasma levels of triglycerides and increases fasting plasma glucose levels in the apolipoprotein CIII transgenic mouse model of hypertriglyceridemia when administered at a dose of 10 mg/kg. Formulations containing ciprofibrate have been used in the treatment of hypertriglyceridemia.

Chemical Properties

Off-White to Pale Beige Solid

Originator

Sterling-Wintbrop (USA)

Uses

Peroxisome proliferator-activated receptor α (PPARα) is a ligand-activated transcription factor involved in the regulation of lipid homeostasis. Activation of PPARα results in expression of a variety of genes, particularly those involved in fatty acid β-oxidation, binding, and transport. Ciprofibrate activates PPARα with an EC50 value of 20 μM and only marginally affects PPARγ (EC50 = >300 μM). It has been shown to lower adipose tissue weight and reduce plasma insulin concentrations in obese rats and has been used clinically in the treatment of dyslipidemia. Ciprofibrate reportedly stimulates cholesteryl ester transfer protein expression and improves the flow of cholesterol through the indirect reverse cholesterol transport system, preserving plasma HDL.

Uses

antihyperlipidemic

Uses

Ciprofibrate is a hypolipemic agent, related structurally to Clofibrate (C586910). Ciprofibrate is used as an antilipemic.

Definition

ChEBI: Ciprofibrate is a monocarboxylic acid, a member of cyclopropanes and an organochlorine compound. It has a role as an antilipemic drug.

Manufacturing Process

A mixture of 8 g (0.0356 mol) of p-(2,2-dichlorocyclopropyl)phenol, 11.2 g (0.28 mol) of sodium hydroxide pellets, 11 g of chloroform and 350 ml of acetone was prepared at 0°C. The cooling bath was removed, the mixture stirred for a minute and then heated on a steam bath to reflux temperature. The reaction mixture was stirred at reflux for three hours and then concentrated in vacuo. The residual gum was partitioned between dilutehydrochloric acid and ether, and the ether layer was separated, dried and concentrated in vacuo. The residual oil (14 g) was partitioned between dilute aqueous sodium bicarbonate and ether. The sodium bicarbonate solution was acidified with concentrated hydrochloric acid and extracted with ether. The ether solution was dried over anhydrous sodium sulfate and concentrated. The residue (9.5 g of yellow oil) was crystallized twice from hexane to give 6.0 g of 2-[p-(2,2-dichlorocyclopropyl)phenoxy]-2-methyl propionic acid in the form of a pale cream-colored solid, MP 114°C to 116°C.

brand name

LJPANOR

Therapeutic Function

Antihyperlipidemic

World Health Organization (WHO)

The safety profile of ciprofibrate is similar to that of clofibrate. See also under clofibrate in full edition.

Biochem/physiol Actions

Peroxisome proliferator-activated receptor α (PPARα) agonist

Clinical Use

Hyperlipidaemia

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: increased risk of myopathy with daptomycin - try to avoid concomitant use.
Anticoagulants: enhances effect of coumarins and phenindione. Dose of anticoagulant should be reduced by up to 50% and readjusted by monitoring INR.
Antidiabetics: may improve glucose tolerance and have an additive effect with insulin or sulphonylureas.
Colchicine: possible increased risk of myopathy.
Lipid-regulating drugs: increased risk of myopathy in combination with statins and ezetimibe (Do not exceed 10 mg of simvastatin and 20 mg of rosuvastatin.1 ) - avoid with ezetimibe.

Metabolism

Approximately 30-75% of a single dose administered to volunteers was excreted in the urine in 72 hours, either as unchanged ciprofibrate (20-25% of the total excreted) or as a glucuronide conjugate. Subjects with moderate renal impairment excreted on average 7% of a single dose as unchanged ciprofibrate over 96 hours, compared with 6.9% in normal subjects. In subjects with severe insufficiency this was reduced to 4.7%.

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