Teriflunomide

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

What is the Teriflunomide?

The molecule Teriflunomide presents a molecular formula of C12H9F3N2O2 and its IUPAC name is (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide.

Teriflunomide (Aubagio) is a disease-modifying antirheumatic drug (DMARD) that works by reducing inflammation and joint damage caused by rheumatoid arthritis (RA). It is a oral medication taken once daily..

The most common side effects of teriflunomide are diarrhea, nausea, hair loss, and elevated liver enzymes. Teriflunomide can also cause serious side effects, such as liver damage, blood disorders, and nervous system problems..

Teriflunomide is a prodrug that is metabolized in the liver to the active metabolite, teriflunomide. Teriflunomide is a selective inhibitor of dihydroorotate dehydrogenase (DHODH), an enzyme involved in the de novo synthesis of pyrimidine nucleotides..

Inhibition of DHODH results in the reduction of intracellular levels of pyrimidine nucleotides, which leads to the inhibition of proliferation of lymphocytes. Teriflunomide is thought to exert its therapeutic effect in RA by reducing the number of activated lymphocytes in the peripheral blood and joints..

Teriflunomide is approved for the treatment of adults with relapsing forms of multiple sclerosis (MS). The recommended dose of teriflunomide is 7 mg once daily..

Teriflunomide is generally well-tolerated. The most common side effects of teriflunomide are diarrhea, nausea, hair loss, and elevated liver enzymes. Teriflunomide can also cause serious side effects, such as liver damage, blood disorders, and nervous system problems..

Patients should be advised to take teriflunomide with food and to drink plenty of fluids to prevent dehydration. Teriflunomide should be used with caution in patients with liver impairment and should be avoided in patients with severe liver impairment..

Teriflunomide is a pregnancy Category X drug and should not be used by women who are pregnant or who may become pregnant. Women of childbearing potential should use effective birth control during treatment with teriflunomide and for at least 2 years after stopping treatment..

Men treated with teriflunomide should use effective birth control during treatment and for at least 3 years after stopping treatment. Teriflunomide is secreted in human milk and should not be used by women who are breastfeeding..

3D structure

Cartesian coordinates

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

2D drawing

 

Teriflunomide UTNUDOFZCWSZMS-YFHOEESVSA-N chemical compound 2D structure molecule svg
Teriflunomide

 

Molecule descriptors

 
IUPAC name(Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
InChI codeInChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
InChI KeyUTNUDOFZCWSZMS-YFHOEESVSA-N
SMILESC/C(O)=C(\C#N)C(=O)Nc1ccc(C(F)(F)F)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.

  • (2Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide (Teriflunomide)
  • (2z)-2-Cyano-3-Hydroxy-N-[4-(Trifluoromethyl)phenyl]but-2-Enamide
  • (E/Z)-Teriflunomide
  • (Z)-2-Cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide
  • (Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide
  • (Z)-2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide.
  • (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
  • (Z)-2-cyano-alpha,alpha,alpha-trifluoro-3-hydroxy-p-crotonotoluidide
  • 108605-62-5
  • 163451-81-8
  • 163451-81-8 (Z Isomer) , 108605-62-5 (E/Z Mixture)
  • 1C058IKG3B
  • 2-BUTENAMIDE, 2-CYANO-3-HYDROXY-N-(4-(TRIFLUOROMETHYL)PHENYL)-, (2Z)-
  • 2-Butenamide, 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)-
  • 2-Butenamide, 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)-, (Z)-
  • 2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-
  • 2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-, (2Z)-
  • 2-Cyano-3-OH-N-(4-trifluoromethylphenyl)croton amide
  • 2-Cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)-2-butenamide
  • 2-Cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide (E/Z)-mixture
  • 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2Z-butenamide
  • 2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-2-butenamide
  • 2-hydroxyethylidene-cyanoacetic acid-4-trifluoromethyl anilide
  • A 1726
  • A 77-1726
  • A 77-1726;A771726;HMR1726;CAS# 108605-62-5
  • A 771726
  • A-771726
  • A26
  • A77 1726
  • A77-1726
  • A771726
  • A801897
  • A882574
  • AB01565775_02
  • AC-26446
  • Aubagio
  • BDBM50018011
  • CCG-267145
  • CS-0033021
  • D10172
  • DB08880
  • DIMETHYL APROBARBITAL
  • Flucyamide
  • GTPL6844
  • HMR 1726
  • HMR-1726
  • HMR1726
  • HY-110159
  • J-010046
  • LE-0275
  • Leflunomide EP Impurity B
  • Leflunomide Impurity B
  • Leflunomide Related Compound B
  • Leflunomide related compound b rs
  • Leflunomide-d4 Metabolite (Teriflunomide-d4)
  • MFCD00910058
  • Malononitrilamide
  • N-(4-Trifluoromethylphenyl)-2-cyano-2-hydroxycrotonamide
  • N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide
  • N-[4-(Trifluoromethyl)phenyl]-2-cyano-3-hydroxycrotonamide
  • NCGC00263218-07
  • NCGC00263218-13
  • NSC-766118
  • NSC766118
  • Q3077133
  • RS 61980
  • RS-61980
  • SU 20
  • SU-0020
  • SW219377-1
  • T3287
  • Teriflunomide
  • Teriflunomide (USAN)
  • Teriflunomide(A-771726)
  • Teriflunomide(Random Configuration)
  • Teriflunomide, A77 1726
  • Teriflunomide; Leflunomide USP RC B; Cyano Keto leflunomide impurity; N-(4-Trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide; 2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-beuteamide
  • s4169
  • teriflunomida
  • teriflunomidum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13512456
  • UNII-1C058IKG3B
  • AKOS015994773
  • DTXSID80893457
  • CHEBI:68540
  • SCHEMBL22661

Physico-Chemical properties

IUPAC name(Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
Molecular formulaC12H9F3N2O2
Molecular weight270.207
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity61.02
LogP3.1
Topological polar surface area73.1

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.