52214-84-3 Usage
Description
Different sources of media describe the Description of 52214-84-3 differently. You can refer to the following data:
1. 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.
2. 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.
Chemical Properties
Off-White to Pale Beige Solid
Originator
Sterling-Wintbrop (USA)
Uses
Different sources of media describe the Uses of 52214-84-3 differently. You can refer to the following data:
1. Ciprofibrate is a hypolipemic agent, related structurally to Clofibrate (C586910). Ciprofibrate is used as an antilipemic.
2. 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.
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
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%.
Check Digit Verification of cas no
The CAS Registry Mumber 52214-84-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,2,1 and 4 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 52214-84:
(7*5)+(6*2)+(5*2)+(4*1)+(3*4)+(2*8)+(1*4)=93
93 % 10 = 3
So 52214-84-3 is a valid CAS Registry Number.
InChI:InChI=1/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)
52214-84-3Relevant articles and documents
Cyclopropanecarboxylic bethe synthetic method
-
Paragraph 0014, (2018/04/01)
The invention relates to a synthesis method of ciprofibrate. In the synthesis method, acetic acid-4-(2,2-dichlorocyclopropyl) phenyl ester is adopted as a raw material, and 2-[4-(2,2-dichlorocyclopropyl) phenoxy]-2-methylpropanoic acid is obtained through alcoholysis, alkylation and alkaline hydrolysis processes. The synthesis method of ciprofibrate, provided by the invention, has the benefits that the raw materials used in the whole reaction are inexpensive and easy to get, the reaction conditions are mild, the operation is convenient, the yield is good, all solvents used in the reaction can be recycled, and the environmental pollution degree is low.
A method for preparing the fat cumaric acupoint of the c bethe method
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, (2017/10/07)
The invention discloses a method for preparing a hypolipidemic medicine ciprofibrate with p-coumaric acid. The method comprises the following specific steps: p-coumaric acid (I) is subjected to a decarboxylation reaction under the effect of an alkaline catalyst, such that p-hydroxystyrene (II) is obtained; p-hydroxystyrene (II) is subjected to a reaction with 2-haloisobutyrate under the effect of alkali, such that an etherified product (III) is obtained; under an alkaline condition, the etherified product (III) and chloroform are subjected to a cyclization reaction under the effect of a phase transfer catalyst, such that a cyclized product (IV) is obtained; the cyclized product (IV) is subjected to alcoholysis and acidification in an alkali solution; and recrystallization is carried out, such that ciprofibrate (V) is obtained. The method provided by the invention has the advantages of short synthesis process, safe operation and easy post-treatment. The method is suitable for large-scale industrialized productions, and almost has no possibility of causing accidents such as explosion. During the entire reaction process, only conventional acid, alkali and solvent are used, such that the cost is low. The solvent can be recovered and reused, such that the method is environment-friendly. With the method, the yield is improved by more than 20%.
Treatment of skin conditions by use of PPAR alpha activators
-
, (2008/06/13)
Disorders of the skin and mucous membrane that have a disrupted or dysfunctional epidermal barrier are treated or prevented by topical application of compounds that are either activators of the farnesoid X receptor, activators of the peroxisome proliferator-activated receptor alpha , and oxysterol activators of the LXR alpha receptor. The same compounds are also effective in treating disorders of epidermal differentiation and proliferation.
