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].
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2D Structure
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Physico-chemical Properties
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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
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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)
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Summary of Clinical Use Click here for help
Flibanserin was approved for use as a non-hormonal treatment for pre-menopausal women with acquired, generalised hypoactive sexual desire disorder (HSDD) in August 2015. Flibanserin is approved with a 'Boxed Warning' to highlight the risks of severe hypotension and syncope in patients who drink alcohol whilst taking this drug. Click here to link to ClinicalTrials.gov's full list of Phase 3 flibanserin trials.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Flibanserin targets 5-HT1A and 5-HT2A receptors in selective brain areas [1] and helps to restore the balance between inhibitory serotonin and and excitatory dopamine/noradrenaline effects believed to be requisite for a healthy sexual response.