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Fenofibric acid

Product NameFenofibric acid
CAS42017-89-0
MFC17H15ClO4
MW318.75
EINECS255-626-9
MOL File42017-89-0.mol

Chemical Properties

Melting point	177-179°C
Boiling point	486.5±35.0 °C(Predicted)
Density	1.286±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
pka	3.09±0.10(Predicted)
form	powder
color	White to Off-White
BRN	2058973
Major Application	forensics and toxicology pharmaceutical (small molecule)
InChI	InChI=1S/C17H15ClO4/c1-17(2,16(20)21)22-14-9-5-12(6-10-14)15(19)11-3-7-13(18)8-4-11/h3-10H,1-2H3,(H,20,21)
InChIKey	MQOBSOSZFYZQOK-UHFFFAOYSA-N
SMILES	C(O)(=O)C(OC1=CC=C(C(=O)C2=CC=C(Cl)C=C2)C=C1)(C)C
CAS DataBase Reference	42017-89-0(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn,N
Risk Statements	36/37/38-50/53-22
Safety Statements	26-36/37/39-61-60-24/25
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
RTECS	UA2453000
HazardClass	9
PackingGroup	III
HS Code	29189900
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1
Toxicity	LD50 oral in rat: 1242mg/kg

Usage And Synthesis

Chemical Properties

Fenofibric acid is a white to almost white crystalline powder that is stable under ordinary conditions and has a melting point of 179 – 183°C. Its empirical formula is C17H15ClO4 and molecular weight 318.75. Fenofibric acid is insoluble in water; its solubility increases with pH in buffered media.

Uses

DPP4 inhibitor, antidiabetic

Uses

Fenofibric acid, the active metabolite of fenofibrate. Increases Apolipoprotein A-I–Mediated High-Density Lipoprotein Biogenesis by enhancing transcription of ATP-Binding cassette transporter A1 gene in a liver X receptor–dependent manner.

Uses

Fenofibric acid, the active metabolite of fenofibrate. Increases Apolipoprotein A-Iediated High-Density Lipoprotein Biogenesis by enhancing transcription of ATP-Binding cassette transporter A1 gene in a liver X receptorependent manner

Definition

ChEBI: A monocarboxylic acid that is 2-methylpropanoic acid substituted by a 4-(4-chlorobenzoyl)phenoxy group at position 2. It is a metabolite of the drug fenofibrate.

Synthesis

Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, phenylmethyl ester

1159999-13-9

42017-89-0

General procedure for the synthesis of fenofibric acid from compound (CAS:1159999-13-9): to a solution of compound 104 (5.00 g, 12.2 mmol) in ethanol (150 mL) was added a solution of potassium hydroxide (2.74 g, 48.9 mmol) in ethanol (50 mL). The reaction mixture was heated to reflux and stirred for 16 hours. Upon completion of the reaction, ethanol was removed under vacuum and water (200 mL) was added to the residue. The aqueous solution was washed with ether (2 x 100 mL) to remove nonpolar impurities, followed by acidification of the aqueous solution with 2N HCl to pH 1. The acidified aqueous solution was extracted with ethyl acetate (2 x 150 mL), the organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give compound 105 (3.57 g, 91% yield) as an off-white solid . The product was characterized by 1H NMR (300 MHz, CD3OD): δ 7.75-7.70 (m, 4H), 7.52 (d, J = 8.6 Hz, 2H), 6.96 (d, J = 9.0 Hz, 2H), 1.65 (s, 6H).

Metabolism

Fenofibric acid is primarily conjugated with glucuronic acid and then excreted in urine. A small amount of fenofibric acid is reduced at the carbonyl moiety to a benzhydrol metabolite, which is, in turn, conjugated with glucuronic acid and excreted in urine. In vitro and in vivo metabolism data indicate that fenofibric acid does not undergo oxidative metabolism (e.g. cytochrome P450) to a significant extent. The enzymes CYP1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 do not play a role in the metabolism of fenofibric acid.

References

[1] Patent: WO2009/73138, 2009, A2. Location in patent: Page/Page column 81-82

Preparation Products And Raw materials

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