Fenofibrate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Fenofibrate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Fenofibrate?

The molecule Fenofibrate presents a molecular formula of C20H21ClO4 and its IUPAC name is propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate.

Fenofibrate (brand names include Antara, Fenoglide, Lipofen, and Tricor) is a medication of the fibrate class. It is used to treat abnormal levels of blood lipids (such as high triglycerides). Fenofibrate is primarily used to decrease triglyceride levels and to increase HDL cholesterol levels. HDL cholesterol is often referred to as "good" cholesterol, because it helps remove other forms of cholesterol from the blood. Fenofibrate may also be used to decrease LDL cholesterol levels. LDL cholesterol is often referred to as "bad" cholesterol, because it can build up on the walls of arteries and form plaque, a substance that can lead to heart disease, stroke, and other problems..

Fenofibrate works by increasing the activity of an enzyme called lipoprotein lipase. This enzyme helps break down fats in the blood. Fenofibrate also decreases the activity of an enzyme called acyl-CoA:cholesterol acyltransferase (ACAT). This enzyme helps make cholesterol. By decreasing the activity of this enzyme, fenofibrate decreases the amount of cholesterol made in the body..

Fenofibrate exists as a generic drug and as the brand-name drugs Antara, Fenoglide, Lipofen, and Tricor. Generic drugs usually cost less than the brand-name versions. In some cases, they may not be available in every strength or form as the brand-name drugs..

The FDA has assigned the generic Fenofibrate drugs an "AB" rating, which means they are considered equivalent to the brand-name versions..

Fenofibrate may be used as part of a combination therapy. That means you need to take it with other drugs..

3D structure

Cartesian coordinates

Geometry of Fenofibrate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Fenofibrate YMTINGFKWWXKFG-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Fenofibrate

 

Molecule descriptors

 
IUPAC namepropan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
InChI codeInChI=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
InChI KeyYMTINGFKWWXKFG-UHFFFAOYSA-N
SMILESCC(C)OC(=O)C(C)(C)Oc1ccc(C(=O)c2ccc(Cl)cc2)cc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1-methylethyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
  • 2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoic acid 1-methylethyl ester
  • 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid 1-methyl-ethyl ester
  • 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid 1-methylethyl ester
  • 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid isopropyl ester
  • 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropionic Acid Isopropyl Ester
  • 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoicacidisopropylester
  • 49562-28-9
  • 562F289
  • A827746
  • AB00052196
  • AB00052196-15
  • AB00052196-16
  • AB00052196_17
  • AB00052196_18
  • AB03716
  • AC-4227
  • Ankebin
  • Antara
  • Antara (micronized)
  • BCP21243
  • BDBM50085042
  • BIDD:GT0574
  • BPBio1_000166
  • BRN 2062462
  • BSPBio_000150
  • BSPBio_003162
  • C07586
  • CCG-38996
  • CCRIS 7282
  • CIP-Fenofibrate
  • CS-0892
  • D00565
  • DB-051642
  • DB01039
  • DSSTox_CID_9874
  • DSSTox_GSID_29874
  • DSSTox_RID_78828
  • DivK1c_000557
  • EC 256-376-3
  • EU-0100486
  • Elasterate
  • Elasterin
  • F 6020
  • F0674
  • FENOFIBRATE (MICRONIZED)
  • FENOFIBRATE (MICRONIZED) (fenofibrate
  • FNF
  • FT-0626400
  • FT-0654669
  • Fenobrate
  • Fenofibrate
  • Fenofibrate (JAN/USP/INN)
  • Fenofibrate (Tricor, Trilipix)
  • Fenofibrate IDD-P
  • Fenofibrate delayed release
  • Fenofibrate micronized
  • Fenofibrate,(S)
  • Fenofibrato
  • Fenofibratum
  • Fenogal
  • Fenoglide
  • Fenomax
  • Fenotard
  • Finofibrate
  • Fulcro
  • GRS-027
  • GTPL7186
  • HMS1568H12
  • HMS1921B17
  • HMS2090G20
  • HMS2092B05
  • HMS2095H12
  • HMS2231B14
  • HMS3259K03
  • HMS3261B13
  • HMS3369M13
  • HMS3649D20
  • HMS3655K12
  • HMS3712H12
  • HMS501L19
  • HSDB 7736
  • HY-17356
  • IDI1_000557
  • Isopropyl (4''-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate
  • Isopropyl (4'-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionate
  • Isopropyl 2-(4-(4-chlorobenzoyl)-phenoxy)-2-methylpropanoate
  • Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
  • Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionate
  • Isopropyl 2-(p-(p-chlorobenzoyl)phenoxy)-2-methylpropionate
  • Isopropyl 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropionate
  • Isopropyl 2-[p-(p-chlorobenzoyl)phenoxy]-2-methylpropionate
  • KBio1_000557
  • KBio2_001730
  • KBio2_004298
  • KBio2_006866
  • KBio3_002382
  • KBioGR_000706
  • KBioSS_001730
  • LCP-Feno
  • LCP-FenoChol
  • LF 178
  • LF-178
  • LP00486
  • Lipanthyl
  • Lipantil
  • Lipidex
  • Lipidil
  • Lipifen
  • Lipirex
  • Lipoclar
  • Lipofen
  • Lipofene
  • Liposit
  • Lipsin
  • Lofibra
  • Lopac-F-6020
  • Lopac0_000486
  • Luxacor
  • MFCD00133314
  • MLS000028515
  • MLS001148191
  • MLS002548878
  • MS-2223
  • NC00452
  • NCGC00015437-01
  • NCGC00015437-02
  • NCGC00015437-03
  • NCGC00015437-04
  • NCGC00015437-05
  • NCGC00015437-06
  • NCGC00015437-07
  • NCGC00015437-08
  • NCGC00015437-09
  • NCGC00015437-10
  • NCGC00015437-11
  • NCGC00015437-12
  • NCGC00015437-13
  • NCGC00015437-14
  • NCGC00015437-16
  • NCGC00015437-17
  • NCGC00015437-31
  • NCGC00021475-03
  • NCGC00021475-04
  • NCGC00021475-05
  • NCGC00021475-06
  • NCGC00021475-07
  • NCGC00021475-08
  • NCGC00253945-01
  • NCGC00261171-01
  • NINDS_000557
  • NSC 281319
  • NSC-281319
  • NSC-757822
  • NSC281319
  • NSC757822
  • Nolipax
  • Opera_ID_328
  • Pharmakon1600-01501010
  • Pharmavit
  • Prestwick0_000275
  • Prestwick1_000275
  • Prestwick2_000275
  • Prestwick3_000275
  • Prestwick_217
  • Procetofen
  • Procetofene
  • Procetoken
  • Proctofene
  • Propanoic acid, 2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-, 1-methylethyl ester
  • Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, 1-methylethyl ester
  • Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, 1-methylethylester
  • Protolipan
  • Q-201111
  • Q419724
  • SBI-0050470.P003
  • SDCCGSBI-0050470.P004
  • SMR000058299
  • SPECTRUM1501010
  • SR-01000000091
  • SR-01000000091-16
  • SR-01000000091-2
  • SR-01000000091-5
  • SR-01000000091-6
  • SR-01000000091-8
  • SW196525-4
  • SY052561
  • Secalip
  • Sedufen
  • Supralip
  • TRICOR (MICRONIZED)
  • Tricor
  • Triglide
  • U202363UOS
  • Z2768724415
  • fenofibrate
  • isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate
  • isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoate;Fenofibrate
  • isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
  • propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
  • propan-2-yl 2-{4-[(4-chlorophenyl)carbonyl]phenoxy}-2-methylpropanoate
  • s1794

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC584092
  • CAS-49562-28-9
  • UNII-U202363UOS
  • AKOS005107777
  • ALBB-028958
  • BRD-K50388907-001-05-6
  • BRD-K50388907-001-18-9
  • BRD-K50388907-001-20-5
  • DTXSID2029874
  • CHEMBL672
  • CHEBI:5001
  • Tox21_110147
  • Tox21_300151
  • Tox21_500486
  • Tox21_110147_1
  • EINECS 256-376-3
  • SPBio_001380
  • SPBio_002369
  • SCHEMBL4670
  • Spectrum_001250
  • Spectrum2_001390
  • Spectrum3_001431
  • Spectrum4_000413
  • Spectrum5_001479

Physico-Chemical properties

IUPAC namepropan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
Molecular formulaC20H21ClO4
Molecular weight360.831
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity97.98
LogP4.7
Topological polar surface area52.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.