Clinofibrate

Clinofibrate
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 2-(4-{1-[4-(1-carboxy-1-methylpropoxy)phenyl]cyclohexyl}phenoxy)-2-methylbutanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H36O6
Molar mass468.590 g·mol−1
3D model (JSmol)
SMILES
  • CCC(C)(C(=O)O)OC1=CC=C(C=C1)C2(CCCCC2)C3=CC=C(C=C3)OC(C)(CC)C(=O)O
InChI
  • InChI=1S/C28H36O6/c1-5-26(3,24(29)30)33-22-15-13-20(14-16-22)28(17-8-7-9-18-28)21-11-10-12-23(19-21)34-27(4,6-2)25(31)32/h10-16,19H,5-9,17-18H2,1-4H3,(H,29,30)(H,31,32) ☒N
  • Key:OGGAHXJZRRGBTK-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Clinofibrate (INN; trade name Lipoclin) is pharmaceutical drug of the fibrate class that is used for managing hyperlipidemia and associated conditions.[1] It is sold and marketed in Japan.[2]

Chemically, it is a derivative of bisphenol Z.[3]

Synthesis

The condensation between cyclohexanone (1) and phenol (2) gives bisphenol Z (3).[4] This is treated with chloroform and methyl ethyl ketone (MEK) in the presence of base. The resulting Bargellini reaction gives clinofibrate (4).[5]

Synthesis of clinofibrate

References

  1. ↑ "What is Clinofibrate used for?". Synapse. 14 June 2024.
  2. ↑ "Clinofibrate". DrugBank.
  3. ↑ Takeuchi N, Kukita H, Kajiyama G, Fujiyama M, Ishikawa K, Miki H, Mishima T, Murata K, Asano T (April 1982). "Effect of clinofibrate, a new hypolipidemic agent, on biliary and serum lipids in patients with hyperlipidemia". Atherosclerosis. 42 (2–3): 129–39. doi:10.1016/0021-9150(82)90145-9. PMID 7073798.
  4. ↑ Patil LS, Suryawanshi VS, Pawar OB, Shinde ND (2011). "An Improved, Highly Efficient Method for the Synthesis of Bisphenols". e-Journal of Chemistry. 8 (4): 2016–2019. doi:10.1155/2011/372673.
  5. ↑ US 3716583, Nakamura Y, Aono S, Agatsuma K, Tanaka Y, "Phenoxy carboxylic acid derivative", issued 13 February 1973, assigned to Sumitomo Chemical Company


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