Compound Information | SONAR Target prediction |
Name: | Clofibrate |
Unique Identifier: | LOPAC 00497 |
MolClass: | Checkout models in ver1.5 and ver1.0 |
Molecular Formula: | C12ClH15O3 |
Molecular Weight: | 227.579 g/mol |
X log p: | 8.696 (online calculus) |
Lipinksi Failures | 1 |
TPSA | 35.53 |
Hydrogen Bond Donor Count: | 0 |
Hydrogen Bond Acceptors Count: | 3 |
Rotatable Bond Count: | 5 |
Canonical Smiles: | CCOC(=O)C(C)(C)Oc1ccc(Cl)cc1 |
Class: | Lipid |
Action: | Modulator |
Selectivity: | Lipoprotein lipase |
Generic_name: | Clofibrate |
Chemical_iupac_name: | ethyl 2-(4-chlorophenoxy)-2-methyl-propanoate |
Drug_type: | Approved Drug |
Pharmgkb_id: | PA449045 |
Kegg_compound_id: | C06916 |
Drugbank_id: | APRD00879 |
Melting_point: | < 25 oC (boiling point 148-150°C at 25 mm Hg) |
H2o_solubility: | Insoluble |
Logp: | 3.58 |
Cas_registry_number: | 637-07-0 |
Mass_spectrum: | http://webbook.nist.gov/cgi/cbook.cgi?Spec=C637070&Index=0&Type=Mass&Large=on |
Drug_category: | Anticholesteremic Agents; Antilipemic Agents; ATC:C10AB01; ATC:C10AB03 |
Indication: | For Primary Dysbetalipoproteinemia (Type III hyperlipidemia) that does not respond adequately to diet. |
Pharmacology: | Clofibrate is an antilipidemic agent similar to gemfibrozil. It acts to lower elevated serum lipids by reducing the very low-density lipoprotein fraction (Sf 20-400) rich in triglycerides. Serum cholesterol may be decreased, particularly in those patients whose cholesterol elevation is due to the presence of IDL as a result of Type III hyperlipoproteinemia. Several investigators have observed in their studies that clofibrate may produce a decrease in cholesterol linoleate but an increase in palmitoleate and oleate, the latter being considered atherogenic in experimental animals. The significance of this finding is unknown at this time. Reduction of triglycerides in some patients treated with clofibrate or certain of its chemically and clinically similar analogs may be associated with an increase in LDL cholesterol. Increase in LDL cholesterol has been observed in patients whose cholesterol is initially normal. Animal studies suggest that clofibrate interrupts cholesterol biosynthesis prior to mevalonate formation. |
Mechanism_of_action: | Clofibrate increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. Chylomicrons are degraded, VLDLs are converted to LDLs, and LDLs are converted to HDL. This is accompanied by a slight increase in secretion of lipids into the bile and ultimately the intestine. Clofibrate also inhibits the synthesis and increases the clearance of apolipoprotein B, a carrier molecule for VLDL. |
Organisms_affected: | Humans and other mammals |