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

What is the Etofenamate?

The molecule Etofenamate presents a molecular formula of C18H18F3NO4 and its IUPAC name is 2-(2-hydroxyethoxy)ethyl 2-[3-(trifluoromethyl)anilino]benzoate.

Etofenamate (brand name: Tebamide) is a nonsteroidal anti-inflammatory drug (NSAID) of the fenamate class. It is used to treat pain and inflammation. It was patented in 1969 and approved for medical use in 1974..

Etofenamate is a white to pale yellow powder that is insoluble in water. The molecule has two chiral centers and exists as a racemic mixture of enantiomers..

The fenamate class of NSAIDs includes mefenamic acid, flufenamic acid, meclofenamic acid, and tolmetin. These drugs share a common mechanism of action: they all inhibit cyclooxygenase (COX) enzymes. COX enzymes are responsible for the synthesis of prostaglandins, which are mediators of pain and inflammation..

Etofenamate is more selective for COX-2 than COX-1, meaning that it is more effective at reducing inflammation than pain. It is also more potent than other fenamate NSAIDs..

The most common side effects of etofenamate are gastrointestinal, including nausea, vomiting, diarrhea, and abdominal pain. Other side effects include headache, dizziness, and rash..

Etofenamate should not be used in people with a history of hypersensitivity to fenamate NSAIDs. It should also be used with caution in people with a history of ulcers or gastrointestinal bleeding..

Etofenamate is a prescription drug that exists in tablet and capsule form. It is typically taken three or four times a day..

3D structure

Cartesian coordinates

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

2D drawing


Etofenamate XILVEPYQJIOVNB-UHFFFAOYSA-N chemical compound 2D structure molecule svg


Molecule descriptors

IUPAC name2-(2-hydroxyethoxy)ethyl 2-[3-(trifluoromethyl)anilino]benzoate
InChI codeInChI=1S/C18H18F3NO4/c19-18(20,21)13-4-3-5-14(12-13)22-16-7-2-1-6-15(16)17(24)26-11-10-25-9-8-23/h1-7,12,22-23H,8-11H2

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.

  • 2-(2-Hydroxyaethoxy)aethylester der flutenaminsaeure
  • 2-(2-Hydroxyethoxy)ethyl 2-((3-(trifluoromethyl)phenyl)amino)benzoate
  • 2-(2-Hydroxyethoxy)ethyl N-(alpha,alpha,alpha-trifluoro-m-tolyl)anthranilate
  • 2-(2-Hydroxyethoxy)ethyl-N-(alpha,alpha,alpha-trifluoro-m-tolyl)anthranilate
  • 2-(2-hydroxyethoxy)ethyl 2-[3-(trifluoromethyl)anilino]benzoate
  • 2-(2-hydroxyethoxy)ethyl 2-{[3-(trifluoromethyl)phenyl]amino}benzoate
  • 2-[3-(trifluoromethyl)anilino]benzoic acid 2-(2-hydroxyethoxy)ethyl ester
  • 30544-47-9
  • 544E479
  • AC-35208
  • AS-73948
  • Anthranilic acid, N-(alpha,alpha,alpha-trifluoro-m-tolyl)-, 2-(2-hydroxyethoxy)ethyl ester
  • BAY-D-1107
  • BAYD-1107
  • BCP08746
  • BRN 2953263
  • Bay d 1107
  • Bayrogel
  • Benzoic acid, 2-((3-(trifluoromethyl)phenyl)amino)-, 2-(2-hydroxyethoxy)ethyl ester
  • Benzoic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-, 2-(2-hydroxyethoxy)ethyl ester
  • CCG-220592
  • CS-0905
  • D04102
  • DA-33632
  • DB08984
  • DSSTox_CID_25448
  • DSSTox_GSID_45448
  • DSSTox_RID_80887
  • EX-A275
  • Etofenamate
  • Etofenamate (USAN/INN)
  • Etofenamato
  • Etofenamatum
  • FT-0668428
  • HMS1571K09
  • HMS3713H06
  • HY-17361
  • J-018005
  • KZF0XM66JC
  • MFCD00242806
  • NCGC00016804-01
  • NCGC00016804-02
  • NCGC00016804-03
  • Prestwick0_001014
  • Prestwick1_001014
  • Prestwick2_001014
  • Q414378
  • Rheumon
  • Rheumon gel
  • SR-01000872640
  • SR-01000872640-1
  • TV-485;TV485;TV 485; WHR-5020; WHR 5020; WHR5020
  • TVX 485
  • TVX-485
  • TVX485
  • WHR 5020
  • WHR-5020
  • Z1248763315
  • s6742

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2034516
  • CAS-30544-47-9
  • AKOS026750534
  • BRD-K73541271-001-01-0
  • DTXSID2045448
  • CHEMBL1451633
  • CHEBI:94731
  • Tox21_110618
  • Tox21_110618_1
  • EINECS 250-231-8
  • SPBio_003038
  • SCHEMBL25152

Physico-Chemical properties

IUPAC name2-(2-hydroxyethoxy)ethyl 2-[3-(trifluoromethyl)anilino]benzoate
Molecular formulaC18H18F3NO4
Molecular weight369.335
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity88.94
Topological polar surface area67.8

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.