| Identification | Back Directory | [Name]
Fenofibrate | [CAS]
49562-28-9 | [Synonyms]
lf-178
lipsin
sedufen
LIPYDIL
lipidax
lipifen
Lipirex
Liposit
Nolipax
Secalip
MeltDose
Lipantyl
lipoclar
lipofene
lipantil
LIPANTHYL
Elasterin
proctofene
procetofen
NSC 281319
Fenofibrite
Procetofene
FENOFIBRATE
Lipidil Supra
Fenofibrate API
Fenofibrate COS
Fenofibrate, >=99%
Fenofibrate (200 mg)
LABOTEST-BB LT00771982
isopropyl2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionate
Isopropyl 2-[p-[p-chlorobenzoyl] phenoxy]-2-methylpropionate
isopropyl(4’-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate
2-[4-[p-Chlorobenzoyl]]-2-methylpropionic acid isopropyl ester
propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate
ethyl 2-[4-(4-chlorophenyl)carbonylphenoxy]-2-methyl-propanoate
Propanoic acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-, ethyl ester
2-[p-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid isopropyl ester
propan-2-yl 2-[4-(4-chlorophenyl)carbonylphenoxy]-2-methyl-propanoate
2-[4-(4-CHLOROBENZOYL)PHENOXY]-2-METHYLPROPANOIC ACID ISOPROPYL ESTER
2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propionic acid isopropyl ester
2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-propanoicaci1-methylethylester
2-[4-(4-CHLOROBENZOYL)PHENOXYL-2-METHYLPROPANOIC ACID 1-METHYLETHYL ESTER
2-[4-(4-CHLOROBENZOYL)PHENOXY]-2-METHYL-PROPANOIC ACID, 1-METHYLETHYL ESTER
2-[4-[(4-chlorophenyl)-oxomethyl]phenoxy]-2-methylpropanoic acid ethyl ester
Fenofibrate,2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid isopropyl ester
2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropionic Acid Isopropyl Ester
Isopropyl 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropionate | [EINECS(EC#)]
256-376-3 | [Molecular Formula]
C20H21ClO4 | [MDL Number]
MFCD00133314 | [MOL File]
49562-28-9.mol | [Molecular Weight]
360.83 |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
80-810C | [Boiling point ]
469.8±35.0 °C(Predicted) | [density ]
1.177±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT | [solubility ]
Practically insoluble in water, very soluble in methylene chloride, slightly soluble in ethanol (96 per cent) | [form ]
powder
| [color ]
off-white
| [Water Solubility ]
0.8mg/L(25 ºC) | [Merck ]
14,3978 | [Henry's Law Constant]
2.2×103 mol/(m3Pa) at 25℃, HSDB (2015) | [BCS Class]
2 | [Major Application]
forensics and toxicology
pharmaceutical (small molecule) | [InChI]
InChI=1S/C20H21ClO4/c1-13(2)24-19(23)20(3,4)25-17-11-7-15(8-12-17)18(22)14-5-9-16(21)10-6-14/h5-13H,1-4H3 | [InChIKey]
YMTINGFKWWXKFG-UHFFFAOYSA-N | [SMILES]
C(OC(C)C)(=O)C(OC1=CC=C(C(=O)C2=CC=C(Cl)C=C2)C=C1)(C)C | [EPA Substance Registry System]
Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, 1-methylethyl ester (49562-28-9) |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Usage]
antihyperlipidemic | [Usage]
Antilipemic. It is a lipid regulating drug. Increases high density lipoprotein levels by reducing cholesteryl ester transfer protein expresion. | [Usage]
Cardiovascular disease | [Originator]
Lipantyl,Fournier,France,1975 | [Uses]
antihyperlipidemic | [Uses]
Antilipemic. It is a lipid regulating drug. Increases high density lipoprotein levels by reducing cholesteryl ester transfer protein expresion. | [Uses]
Cardiovascular disease | [Definition]
ChEBI: A chlorobenzophenone that is (4-chlorophenyl)(phenyl)methanone substituted by a [2-methyl-1-oxo-1-(propan-2-yloxy)propan-2-yl]oxy group at position 1 on the phenyl ring. | [Manufacturing Process]
(a) Preparation of p-(4-chlorobenzoyl)-phenoxyisobutyric acid: 1 mol of 4-
hydroxy-4'-chlorobenzophenone is dissolved in anhydrous acetone and then 5
mols of powdered sodium hydroxide is added. The corresponding sodium
phenoxide precipitates. Refluxing is effected, and then, 1.5 mols of CHCl3
diluted with anhydrous acetone is added and the resulting mixture is refluxed
for 10 hours. After cooling, water is added, the acetone is evaporated, the
aqueous phase is washed with ether and acidified and the organic phase is
redissolved in ether and extracted into a solution of bicarbonate. The
bicarbonate solution is than acidified to obtain the desired acid, having a
melting point of 185°C, with a yield of 75%.
(b) Preparation of fenofibrate: 1 mol of the acid obtained is converted into its
acid chloride using thionyl chloride (2.5 mols). 1 mol of the acid chloride is
then condensed with 1.05 mol of isopropyl alcohol in the presence of 0.98 mol
of pyridine in an inert solvent such as benzene.
Since traces of SO2 (which has a bad smell) may be obtained from the thionyl
chloride, it is preferable to avoid this disadvantage by carrying out the
esterification directly. | [Therapeutic Function]
Antihyperlipoproteinemic | [General Description]
Fenofibrate, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoic acid 1-methylethyl ester (Tricor),has structural features represented in clofibrate. The primarydifference involves the second aromatic ring. This imparts agreater lipophilic character than exists in clofibrate, resultingin a much more potent hypocholesterolemic and triglycerideloweringagent. Also, this structural modification results in alower dose requirement than with clofibrate or gemfibrozil. | [Biochem/physiol Actions]
Fenofibrate increases high density lipoprotein levels by reducing cholesteryl ester transfer protein expression. It is used in treating the condition of increased cholesterol levels in the blood, abnormal lipid levels in the body and also hypertriglyceridaemia. Fenofibrate is a lipid regulating drug and proliferator-activated receptor-α (PPARα) mediates its action. It decreases the plasma levels of fibrinogen and C-reactive protein. By this fenofibrate allows better flow-mediated dilatation and reduces the risk of atherosclerosis. Fenofibrate is also known to reduce uric acid levels. | [Clinical Use]
#N/A | [Synthesis]
New synthetic plan for fenofibrate via lithium-based flash chemistry: starting from 4-bromophenol or 4-iodophenol, the aryl halide substrates isopropyl 2-(4-bromophenoxy)-2-methyl propanoate (1) or isopropyl 2-(4-iodophenoxy)-2-methyl propanoate (5) were first prepared on a gram scale; a fast Li-halogen exchange with the sterically hindered lithium reagent MesLi at −50 °C then generated the short-lived ArLi intermediate 2 bearing an aliphatic ester (n-BuLi, sec-BuLi, and PhLi performed poorly owing to their nucleophilic attack on the ester group); this intermediate was sequentially coupled with the electrophile 4-chlorobenzoyl chloride in a 3D-printed static mixer reactor (SMR, R2, Ø 500 µm, L 1.0 cm, connected with capillary reactors R1 and R3 at both ends) to directly afford the diaryl-ketone product fenofibrate in a single flow step, with the best yield of 76% under the optimal conditions of 5 equivalents of 4-chlorobenzoyl chloride in CH₂Cl₂ at a flow rate of 3 mL min−1 [1].
 | [Drug interactions]
Potentially hazardous interactions with other drugs
Antibacterials: increased risk of myopathy with
daptomycin - try to avoid concomitant use.
Anticoagulants: enhances effect of coumarins and
phenindione; dose of anticoagulant should be
reduced by up to 50% and readjusted by monitoring
INR.
Antidiabetics: may improve glucose tolerance
and have an additive effect with insulin or
sulphonylureas.
Ciclosporin: ciclosporin levels appear to be
unaffected; however, it is recommended that
concomitant therapy should be avoided because of
the possibility of elevated serum creatinine levels.
Colchicine: possible increased risk of myopathy.
Lipid-regulating drugs: increased risk of myopathy
in combination with statins and ezetimibe
(maximum 20 mg of rosuvastatin); increased risk of
cholelithiasis and gallbladder disease with ezetimibe
- avoid with ezetimibe. | [Metabolism]
After oral administration, fenofibrate is rapidly
hydrolysed by esterases to the active metabolite fenofibric
acid.No unchanged fenofibrate can be detected in the plasma.
Fenofibric acid is excreted mainly in the urine, mainly as
the glucuronide conjugate, but also as a reduced form of
fenofibric acid and its glucuronide; practically all the drug
is eliminated from the body within 6 days | [storage]
Store at RT | [References]
[1]
Kawale, S. A., Kang, D.-C., Ahn, G.-N., Mottafegh, A., Kang, J.-H., Na, G.-S., Kim, D.-P. (2023). Rapid flow synthesis of fenofibrate via scalable flash chemistry with in-line Li recovery. Chemical Engineering Journal, 477, 147033. https://doi.org/10.1016/j.cej.2023.147033 |
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| Company Name: |
Elucigen bio Gold
|
| Telephone: |
13501719342 13501719342 |
| Website: |
https://www.elucigenbio.com/ |
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|