Rilpivirine

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

What is the Rilpivirine?

The molecule Rilpivirine presents a molecular formula of C22H18N6 and its IUPAC name is 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile.

Rilpivirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used as part of combination antiretroviral therapy (ART) for the treatment of HIV-1 infection. It was approved by the U.S. Food and Drug Administration (FDA) in 2011..

Rilpivirine is sold under the brand name Edurant. It is also available in generic form..

Rilpivirine is an HIV medication that works by blocking the reverse transcriptase enzyme. This enzyme is needed for the HIV virus to multiply..

Rilpivirine is used in combination with other HIV medications to treat HIV-1 infection in adults. This medication is not a cure for HIV-1 infection..

Rilpivirine may also be used for purposes not listed in this medication guide..

3D structure

Cartesian coordinates

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

2D drawing

 

Rilpivirine YIBOMRUWOWDFLG-ONEGZZNKSA-N chemical compound 2D structure molecule svg
Rilpivirine

 

Molecule descriptors

 
IUPAC name4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile
InChI codeInChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+
InChI KeyYIBOMRUWOWDFLG-ONEGZZNKSA-N
SMILESCc1cc(/C=C/C#N)cc(C)c1Nc1ccnc(Nc2ccc(C#N)cc2)n1

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.

  • (E)-3-{4-[2-(p-Cyanophenylamino)-4-pyrimidinylamino]-3,5-xylyl}acrylonitrile; 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile
  • (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile
  • (E)-4-(4-(4-(2-cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile
  • 4-((4-((4-((1E)-2-CYANOETHENYL)-2,6-DIMETHYLPHENYL)AMINO)PYRIMIDIN-2-YL)AMINO)BENZONITRILE
  • 4-((4-((4-((1E)-2-Cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)benzonitrile
  • 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]-2-pyrimidinyl]amino]benzonitrile
  • 4-[[4-[4-[(E)-2-cyanovinyl]-2,6-dimethyl-anilino]pyrimidin-2-yl]amino]benzonitrile
  • 4-[[4-[[4-(2-Cyanoethenyl)-2,6-dimethylphenyl]amino]pyrimidine-2-yl]amino]benzonitrile
  • 4-[[4-[[4-[(E)-2-Cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
  • 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzenecarbonitrile
  • 4-{4-[4-((E)-2-Cyano-vinyl)-2,6-dimethyl-phenylamino]-pyrimidin-2-ylamino}-benzonitrile
  • 4-{[4-({4-[(E)-2-Cyanoethenyl]-2,6-Dimethylphenyl}amino)pyrimidin-2-Yl]amino}benzonitrile
  • 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
  • 500287-72-9
  • 500287-72-9 (free base)
  • A827939
  • AC-30619
  • BCP03563
  • BCP0726000192
  • BCP9000016
  • BDBM222178
  • BENZONITRILE, 4-((4-((4-((1E)-2-CYANOETHENYL)-2,6-DIMETHYLPHENYL)AMINO)-2- PYRIMIDINYL)AMINO)-
  • Benzonitrile, 4-((4-((4-((1E)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)-
  • CABENUVA COMPONENT RILPIVIRINE
  • CCG-268241
  • CS-0440
  • D09720
  • DB08864
  • EX-A245
  • Edurant
  • Edurant(TM)
  • FI96A8X663
  • GTPL11387
  • HSDB 8153
  • HY-10574
  • KE-0036
  • MFCD11046372
  • NCGC00319175-03
  • NCGC00319175-08
  • Q421547
  • R 278474
  • R-278474
  • R278474
  • R278474;TMC278
  • RILPIVIRINE COMPONENT OF CABENUVA
  • Rilpivirina
  • Rilpivirine
  • Rilpivirine (JAN/USAN/INN)
  • Rilpivirine free base
  • Rilpivirine(R 278474, TMC 278)
  • STL484047
  • SW220232-1
  • T27
  • TMC 278
  • TMC-278
  • TMC278
  • W-202888
  • s7303

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1554274
  • UNII-FI96A8X663
  • AKOS015901680
  • DTXSID10198189
  • CHEMBL175691
  • CHEBI:68606
  • SCHEMBL384696
  • SCHEMBL385113

Physico-Chemical properties

IUPAC name4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile
Molecular formulaC22H18N6
Molecular weight366.419
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity110.41
LogP5.1
Topological polar surface area97.4

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.