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
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Clinofibrate (INN) (trade name Lipoclin) is a fibrate and a derivative of Bisphenol Z.[1]

Synthesis

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

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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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