Ciprofibrate

Names

[ Name ]:
Ciprofibrate

[Synonym ]:
2-[p-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid
Ciprofibrate
2-[p-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid,Ciprofibrate
EINECS 257-744-6
MFCD00467135
2-(4-(2,2-Dichlorocyclopropyl)phenoxy)-2-methylpropanoic acid
2-[4-(2,2-Dichlorocyclopropyl)phenoxy]-2-methylpropionic Acid
UNII:F8252JGO9S
2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid

Biological Activity

[Description]:

Ciprofibrate is a peroxisome proliferator-activated receptor agonist.Target: PPARCiprofibrate is a hypolipidemic compound that can induce proliferation of peroxisomes in liver cells of rats. Known to be a PPARα (peroxisome proliferator-activated receptor α) agonist [1, 2].

[Related Catalog]:

Research Areas >> Cancer

[Target]

PPARα

[References]

[1]. Passilly, P., et al., Phosphorylation of peroxisome proliferator-activated receptor alpha in rat Fao cells and stimulation by ciprofibrate. Biochem Pharmacol, 1999. 58(6): p. 1001-8.

[2]. Clemencet, M.C., et al., Differences in cell proliferation in rodent and human hepatic derived cell lines exposed to ciprofibrate. Cancer Lett, 2005. 222(2): p. 217-26.

[Related Small Molecules]

GW9662 | Retinoic acid | Elafibranor | GW501516 | Troglitazone | T0070907 | Pemafibrate | CDDO-Im | Wy-14643 | GW0742 | GW1929 | FH535 | Icariin | Daidzein | Fisetin

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
424.9±45.0 °C at 760 mmHg

[ Melting Point ]:
114 - 118ºC

[ Molecular Formula ]:
C₁₃H₁₄Cl₂O₃

[ Molecular Weight ]:
289.155

[ Flash Point ]:
210.7±28.7 °C

[ Exact Mass ]:
288.032013

[ PSA ]:
46.53000

[ LogP ]:
2.87

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.579

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UF0880000

CHEMICAL NAME :: Propionic acid, 2-(4-(2,2-dichlorocyclopropyl)phenoxy)-2-methyl-

CAS REGISTRY NUMBER :: 52214-84-3

LAST UPDATED :: 199706

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C13-H14-Cl2-O3

MOLECULAR WEIGHT :: 289.17

WISWESSER LINE NOTATION :: L3TJ AG AG BR DOX1&1&VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3640 mg/kg/26W-I

TOXIC EFFECTS :: Liver - changes in liver weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other oxidoreductases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 105 mg/kg/7D-C

TOXIC EFFECTS :: Liver - other changes Liver - changes in liver weight Biochemical - Metabolism (Intermediary) - other proteins

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg/5D-I

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 14560 mg/kg/26W-I

TOXIC EFFECTS :: Liver - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6390 mg/kg/60W-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6720 mg/kg/64W-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7300 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 280 mg/kg

SEX/DURATION :: female 15-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

TYPE OF TEST :: Morphological transformation

TYPE OF TEST :: DNA damage

TYPE OF TEST :: Unscheduled DNA synthesis

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - rat Liver

DOSE/DURATION :: 100 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 286,135,1993

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H350

[ Precautionary Statements ]:
P201-P280-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

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R45

[ Safety Phrases ]:
S53-S22-S36/37/39-S45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UF0880000

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Transcriptional Regulation of Cytosolic Sulfotransferase 1C2 by Intermediates of the Cholesterol Biosynthetic Pathway in Primary Cultured Rat Hepatocytes.

J. Pharmacol. Exp. Ther. 355 , 429-41, (2015)

Cytosolic sulfotransferase 1C2 (SULT1C2) is expressed in the kidney, stomach, and liver of rats; however, the mechanisms regulating expression of this enzyme are not known. We evaluated transcriptiona...

Ciprofibrate increases cholesteryl ester transfer protein gene expression and the indirect reverse cholesterol transport to the liver.

Lipids Health Dis. 8 , 50, (2009)

CETP is a plasma protein that modulates atherosclerosis risk through its HDL-cholesterol reducing action. The aim of this work was to examine the effect of the PPARalpha agonist, ciprofibrate, on the ...

Ciprofibrate, clofibric acid and respective glycinate derivatives. Effects of a four-week treatment on male lean and obese Zucker rats.

Arzneimittelforschung 58(5) , 225-41, (2008)

Fibrates are widely prescribed in hyperlpidemic patients to prevent atherosclerosis. Their therapeutic use, however, can be associated with adverse effects like gastrointestinal disorders, myalgia, my...