Clinofibrate

Clinofibrate
Clinical data
AHFS/Drugs.com	International 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	30299-08-2 ;
PubChem CID	2787;
DrugBank	DB09006 ;
ChemSpider	21613360 ;
UNII	0374EZJ8CU;
KEGG	D01300 ;
ChEMBL	ChEMBL1897738 ;
CompTox Dashboard (EPA)	DTXSID6046638 ;
Chemical and physical data
Formula	C28H36O6
Molar mass	468.590 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:OGGAHXJZRRGBTK-UHFFFAOYSA-N ;
	(what is this?) (verify)

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]

^ 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.
^ 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.
^ 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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Clinical data

AHFS/Drugs.com	International 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	30299-08-2^Y
PubChem CID	2787
DrugBank	DB09006^N
ChemSpider	21613360^N
UNII	0374EZJ8CU
KEGG	D01300^Y
ChEMBL	ChEMBL1897738^N
CompTox Dashboard (EPA)	DTXSID6046638
Chemical and physical data
Formula	C₂₈H₃₆O₆
Molar mass	468.590 g·mol⁻¹
3D model (JSmol)	Interactive image
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
^NY (what is this?) (verify)