flibanserin   Click here for help

GtoPdb Ligand ID: 8182

Synonyms: Addyi® | BIMT-17 | Girosa® (proposed trade name)
Approved drug
flibanserin is an approved drug (FDA (2015))
Compound class: Synthetic organic
Comment: Flibanserin is reported as a serotonin 5-HT1A agonist and 5-HT2A antagonist [2]. The compound was originally investigated as a antidepressant [3-4].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 44.27
Molecular weight 390.17
XLogP 3.31
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES O=c1[nH]c2c(n1CCN1CCN(CC1)c1cccc(c1)C(F)(F)F)cccc2
Isomeric SMILES O=c1[nH]c2c(n1CCN1CCN(CC1)c1cccc(c1)C(F)(F)F)cccc2
InChI InChI=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)
1. Allers KA, Dremencov E, Ceci A, Flik G, Ferger B, Cremers TI, Ittrich C, Sommer B. (2010)
Acute and repeated flibanserin administration in female rats modulates monoamines differentially across brain areas: a microdialysis study.
J Sex Med, 7 (5): 1757-67. [PMID:20163532]
2. Borsini F, Evans K, Jason K, Rohde F, Alexander B, Pollentier S. (2002)
Pharmacology of flibanserin.
CNS Drug Rev, 8 (2): 117-42. [PMID:12177684]
3. D'Aquila P, Monleon S, Borsini F, Brain P, Willner P. (1997)
Anti-anhedonic actions of the novel serotonergic agent flibanserin, a potential rapidly-acting antidepressant.
Eur J Pharmacol, 340 (2-3): 121-32. [PMID:9537806]
4. Invernizzi RW, Sacchetti G, Parini S, Acconcia S, Samanin R. (2003)
Flibanserin, a potential antidepressant drug, lowers 5-HT and raises dopamine and noradrenaline in the rat prefrontal cortex dialysate: role of 5-HT(1A) receptors.
Br J Pharmacol, 139 (7): 1281-8. [PMID:12890707]