CAS 52214-84-3|ciprofibrate|2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid|Ciprofibrate|2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoic acid|Lipanor|(±)-Ciprofibrate|Win 358...

General Information

Structure

Molecular Formula

C₁₃H₁₄Cl₂O₃

Molecular Mass

289.15446

Exact Mass

288.03199967

Charge

InChI

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)

InChIKey

KPSRODZRAIWAKH-UHFFFAOYSA-N

Canonic Smiles

OC(=O)C(Oc1ccc(cc1)C1CC1(Cl)Cl)(C)C

Isomeric Smiles

c1c(ccc(c1)OC(C(=O)O)(C)C)C1C(C1)(Cl)Cl

Calculated Properties

JChem

Acid pKa

3.6873658

H Acceptors

H Donor

LogD (pH = 5.5)

1.8113741

LogD (pH = 7.4)

0.3118669

Log P

3.6223862

Molar Refractivity

70.5022

Polarizability

27.351288

Polar Surface Area

46.53

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

ciprofibrate 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Synonyms

Ciprofibrate2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoic acidLipanor(±)-Ciprofibrate2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropanoic AcidModalim2-[p-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropionic AcidWin 35833Ciprol2-[p-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropanoic acidCiprofibrate

IUPAC name

2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Names and Identifiers

Registration numbers

CAS Number

EC Number

MDL Number

PubChem SID

PubChem CID

Registration numbers

Properties

Product Information

Free Base

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Effective in type Iia, Iib, III and IV hyperlipoproteinaemias and increases high-density lipoprotein

Hypolipidaemic agent

95+%

Pharmacology Properties

human ... PPARA(5465)

Agonist of the PPARalpha receptor in muscle, liver, and other tissues

Properties

Related Proteins

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Molecular Spectra

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Molecule Details

Selleck Chemicals

S2665

Research Area: Cardiovascular Disease
Biological Activity:
Ciprofibrate is a peroxisome proliferator-activated receptor agonist. [1] It was reported that ciprofibrate decreased the levels of plasma triglycerides and total cholesterol as well as low-density lipoprotein cholesterol. Meanwhile, ciprofibrate elevated plasma levels of high-density lipoprotein cholesterol. The maximum concentration time of ciprofibrate is between one hour and 2.5 hours while the long half life (80 -100 h) permits daily dosing of the drug. In addition, the maximum plasma concentration is between 66 and 88 μg/mL after chronic administration of 100 mg/day of ciprofibrate. Ciprofibrate belongs to the second generation of fibric acid derivatives which used to treat patients with dyslipidaemias of various types. [2]

Sigma Aldrich

C0330

Biochem/physiol Actions
Peroxisome proliferator-activated receptor α (PPARα) agonist
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C0330.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

C482475

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

Molecule Details

References

PubChem Literature

From Data Sources

• Steed MM et al. Antioxid Redox Signal. 2011 Oct 1;15(7):1927-43.

• Arnold, A., et al.: J. Pharm. Sci., et al.: 68, 1557 (1975)

• Tuchman-Duplessis, H., et al.: Toxicology, 12, 1 (1975)

• Davison, C., et al.: Drug. Metab. Dispos., 3, 520 (1975)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1304

• Gibson, G. et al., Peroxisomes: Biology and Importance in Toxicology and Medicine, Taylor and Francis, London, 1993, (rev)

• Chapman, M.J. et al., Atherosclerosis (Amsterdam), 1996, 124; S83, (pharmacol, use)

• Beyer, K.H. et al., Arch. Pharm. (Weinheim, Ger.), 1982, 315, 1049, (metab)

• Masnatta, L.D. et al., J. Chromatogr., B: Biomed. Appl., 1996, 687, 437, (hplc)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMS210

• Arnold, A. et al., J. Pharm. Sci., 1979, 68, 1557, (props)

• Fr. Pat., 1974, Sterling Drug, 2 197 586; CA, 82, 43059m, (synth, pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity