Flibanserin

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

What is the Flibanserin?

The molecule Flibanserin presents a molecular formula of C20H21F3N4O and its IUPAC name is 3-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one.

Flibanserin (Addyi) is a novel, non-hormonal, multifunctional serotonin agonist and reuptake inhibitor (MSRI) for the treatment of hypoactive sexual desire disorder (HSDD) in premenopausal women. Flibanserin works by modulating the neurotransmitters in the brain, which are thought to play a role in sexual arousal and desire..

HSDD is a condition characterized by low sexual desire that causes distress and/or interpersonal difficulty. It is estimated to affect up to one in ten women. While there are many potential causes of HSDD, the exact cause is unknown in the majority of cases..

Flibanserin was originally developed as an antidepressant, but was found to have limited efficacy in that indication. However, in clinical trials for HSDD, flibanserin was found to be effective in increasing sexual desire and decreasing distress..

The most common side effects of flibanserin include dizziness, nausea, fatigue, and insomnia. Flibanserin is not currently approved for use in any other country..

Flibanserin is a promising new treatment for HSDD, but further research is needed to determine its long-term safety and efficacy..

3D structure

Cartesian coordinates

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

2D drawing

 

Flibanserin PPRRDFIXUUSXRA-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Flibanserin

 

Molecule descriptors

 
IUPAC name3-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one
InChI codeInChI=1S/C20H21F3N4O/c21-20(22,23)15-4-3-5-16(14-15)26-11-8-25(9-12-26)10-13-27-18-7-2-1-6-17(18)24-19(27)28/h1-7,14H,8-13H2,(H,24,28)
InChI KeyPPRRDFIXUUSXRA-UHFFFAOYSA-N
SMILESO=c1[nH]c2ccccc2n1CCN1CCN(c2cccc(C(F)(F)F)c2)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.

  • 1,3-Dihydro-1-(2-(4-(3-(trifluoromethyl)phenyl)-1-piperazinyl)ethyl)-2H-benzimidazol-2-one
  • 1,3-Dihydro-1-[2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl]-2H-benzimidazol-2-one
  • 1-(2-(4-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)-1-PIPERAZINYL)ETHYL)-2-BENZIMIDAZOLINONE
  • 1-(2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethyl)-1H-benzo[d]imidazol-2(3H)-one
  • 1-(2-(4-(3-Trifluoromethylphenyl)piperazin-1-yl)ethyl)benzimidazol(1H)-2-one
  • 1-(2-(4-(alpha,alpha,alpha-Trifluoro-m-tolyl)-1-piperazinyl)ethyl)-2-benzimidazolinone
  • 1-(2-(4-alpha,alpha,alpha-Trifluoro-m-tolyl)-1-(piperazinyl)ethyl)-2-benzimidazolinone
  • 1-(2-(4-alpha,alpha,alpha-Trifluoro-m-tolyl)-1-piperazinyl)ethyl)-2-benzimidazolinone
  • 1-(2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl)-1,3-dihydro-2H-benzimidazol-2-one
  • 1-[2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethyl]benzimidazol-[1H]-2-one
  • 167933-07-5
  • 2H-Benzimidazol-2-one, 1,3-dihydro-1-[2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl]-
  • 2H-Benzimidazol-2-one,1,3-dihydro-1-[2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl]-
  • 3-[2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl]-1H-benzimidazol-2-one
  • 3-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one
  • 37JK4STR6Z
  • 933F075
  • A810922
  • AM84577
  • Addyi
  • BCP02131
  • BDBM50476735
  • BIMT 17 BS
  • BIMT 17BS
  • BIMT-17-BS
  • BIMT-17BS
  • Bimt 17
  • Bimt-17
  • CCG-268528
  • CS-4671
  • D02577
  • DB04908
  • EX-A2807
  • Ectris
  • F1239
  • FT-0659246
  • Female Viagra (Street Name)
  • Filbanserin.
  • Flibanserin
  • Flibanserin (USAN/INN)
  • Flibanserin; BIMT-17; BIMT-17BS
  • GTPL8182
  • Girosa
  • Girosa (proposed trade name)
  • HMS3885K21
  • HSDB 8278
  • HY-A0095
  • L001463
  • MFCD00918402
  • NCGC00386567-01
  • NCGC00386567-02
  • NCGC00386567-03
  • Q415996
  • s3716

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC52716421
  • UNII-37JK4STR6Z
  • AKOS005146139
  • CHEMBL231068
  • CHEBI:90865
  • SCHEMBL247579

Physico-Chemical properties

IUPAC name3-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one
Molecular formulaC20H21F3N4O
Molecular weight390.402
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity109.41
LogP3.2
Topological polar surface area44.3

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.