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Details

Stereochemistry ACHIRAL
Molecular Formula C20H21F3N4O.ClH
Molecular Weight 426.863
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLIBANSERIN HYDROCHLORIDE

SMILES

Cl.FC(F)(F)C1=CC=CC(=C1)N2CCN(CCN3C(=O)NC4=C3C=CC=C4)CC2

InChI

InChIKey=XGAGFLQFMFCIHZ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

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. Flibansetrin has high affinity for serotonin receptors in the brain: it acts as an agonist on 5-HT1A and an antagonist on 5-HT2A. In vivo, flibanserin binds equally to 5-HT1A and 5-HT2A receptors. However, under higher levels of brain 5-HT (i.e., under stress), flibanserin may occupy 5-HT2A receptors in higher proportion than 5-HT(1A) receptors. It may also moderately antagonize D4 (dopamine) receptors and 5-HT2B and 5-HTB2C. Its action on neurotransmitter receptors may contribute to reduction in serotonin levels and increase in dopamine and norepinephrine levels, all of which may play part in reward processing. Flibanserin is sold under the trade name Addyi and indicated for the treatment of premenopausal women with acquired, generalized hypoactive sexual desire disorder (HSDD) as characterized by low sexual desire that causes marked distress or interpersonal difficulty.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.31 null [pKi]
4.0 nM [EC50]
115.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ADDYI

Cmax

ValueDoseCo-administeredAnalytePopulation
419 ng/mL
100 mg single, oral
FLIBANSERIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1543 ng × h/mL
100 mg single, oral
FLIBANSERIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
100 mg single, oral
FLIBANSERIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
100 mg single, oral
FLIBANSERIN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Recommended dosage is 100 mg taken once daily at bedtime, discontinue treatment after 8 weeks if no improvement
Route of Administration: Oral
In Vitro Use Guide
The concentration that reduces forskolin-induced cAMP formation by 50% in human hippocampus tissue was 4 nM.