Flibanserin hydrochlorideProduct ingredient for Flibanserin

Name
Flibanserin hydrochloride
Drug Entry
Flibanserin

Flibanserin is the first drug to be approved for hypoactive sexual desire disorder (HSDD) in premenopausal women by the FDA in August 2015. It was originally developed as an antidepressant medication by Boehringer Ingelheim, but showed lack of efficacy in trials and was further developed as a hypoactive sexual disorder drug by Sprout Pharmaceuticals. Flibanserin's mechanism of action is attributed to its high affinity for 5-HTA1 and 5-HTA2 receptors, displaying agonist activity on 5-HTA1 and antagonist on 5-HTA2, resulting in lowering of serotonin in the brain as well as an effect on increasing norepinephrine and dopamine neurotransmitters.

Accession Number
DBSALT001321
Structure
Synonyms
Flibanserin HCl
UNII
96XTC36K1B
CAS Number
147359-76-0
Weight
Average: 426.87
Monoisotopic: 426.1434235
Chemical Formula
C20H22ClF3N4O
InChI Key
XGAGFLQFMFCIHZ-UHFFFAOYSA-N
InChI
InChI=1S/C20H21F3N4O.ClH/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);1H
IUPAC Name
1-(2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl)-2,3-dihydro-1H-1,3-benzodiazol-2-one hydrochloride
SMILES
Cl.FC(F)(F)C1=CC(=CC=C1)N1CCN(CCN2C(=O)NC3=CC=CC=C23)CC1
ChemSpider
8021107
Predicted Properties
PropertyValueSource
Water Solubility0.178 mg/mLALOGPS
logP3.32ALOGPS
logP3.83Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.91Chemaxon
pKa (Strongest Basic)7.03Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area38.82 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity103.65 m3·mol-1Chemaxon
Polarizability39.22 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon