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

• ChemBase ID: 73170
• Molecular Formular: C13H14Cl2O3
• Molecular Mass: 289.15446
• Monoisotopic Mass: 288.03199967
• SMILES: c1c(ccc(c1)OC(C(=O)O)(C)C)C1C(C1)(Cl)Cl
• Canonical SMILES: OC(=O)C(Oc1ccc(cc1)C1CC1(Cl)Cl)(C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
• IUPAC Traditional name: ciprofibrate; 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
• Synonyms: Ciprofibrate; 2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropanoic Acid; (±)-Ciprofibrate; 2-[p-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropionic Acid; Ciprol; Lipanor; Modalim; Win 35833; 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methylpropanoic acid; 2-[p-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid; Ciprofibrate

Database IDs

• CAS Number: 52214-84-3
• EC Number: 257-744-6
• MDL Number: MFCD00467135
• PubChem SID: 162038090; 24278288
• PubChem CID: 2763

CALCULATED PROPERTIES

• Acid pKa: 3.6873658
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.8113741
• LogD (pH = 7.4): 0.3118669
• Log P: 3.6223862
• Molar Refractivity: 70.5022 cm^3
• Polarizability: 27.351288 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: UF0880000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... PPARA(5465)
• Mechanism of Action: Agonist of the PPARalpha receptor in muscle, liver, and other tissues

Product Information

• Purity: 95+%; 97%
• Salt Data: Free Base
• Application(s): Effective in type Iia, Iib, III and IV hyperlipoproteinaemias and increases high-density lipoprotein; Hypolipidaemic agent

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.

Toronto Research Chemicals - C482475

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

REFERENCES

• Steed MM et al. Antioxid Redox Signal. 2011 Oct 1;15(7):1927-43.
• Davison, C., et al.: Drug. Metab. Dispos., 3, 520 (1975)
• Arnold, A., et al.: J. Pharm. Sci., et al.: 68, 1557 (1975)
• Tuchman-Duplessis, H., et al.: Toxicology, 12, 1 (1975)
• Fr. Pat., 1974, Sterling Drug, 2 197 586; CA, 82, 43059m, (synth, pharmacol)
• Arnold, A. et al., J. Pharm. Sci., 1979, 68, 1557, (props)
• Beyer, K.H. et al., Arch. Pharm. (Weinheim, Ger.), 1982, 315, 1049, (metab)
• 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)
• Masnatta, L.D. et al., J. Chromatogr., B: Biomed. Appl., 1996, 687, 437, (hplc)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1304
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMS210