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Details

Stereochemistry ACHIRAL
Molecular Formula C20H21F3N4O
Molecular Weight 390.4021
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLIBANSERIN

SMILES

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

InChI

InChIKey=PPRRDFIXUUSXRA-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C20H21F3N4O
Molecular Weight 390.4021
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Anti-anhedonic actions of the novel serotonergic agent flibanserin, a potential rapidly-acting antidepressant.
1997 Dec 11
Further characterisation of potential antidepressant action of flibanserin.
2001 Dec
Mechanism of action of flibanserin in the learned helplessness paradigm in rats.
2001 Dec 14
Ex vivo binding of flibanserin to serotonin 5-HT1A and 5-HT2A receptors.
2001 Feb
Lack of interaction between flibanserin and antidepressants in inducing serotonergic syndrome in rats.
2001 Mar
Region-dependent effects of flibanserin and buspirone on adenylyl cyclase activity in the human brain.
2002 Jun
Forecasting the oral absorption behavior of poorly soluble weak bases using solubility and dissolution studies in biorelevant media.
2002 Mar
Pharmacology of flibanserin.
2002 Summer
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.
2003 Aug
Association of the C(-1019)G 5-HT1A functional promoter polymorphism with antidepressant response.
2004 Dec
Predicting the precipitation of poorly soluble weak bases upon entry in the small intestine.
2004 Jan
Redistribution of the water channel protein aquaporin-4 and the K+ channel protein Kir4.1 differs in low- and high-grade human brain tumors.
2005 Apr
Agonist and antagonist properties of antipsychotics at human dopamine D4.4 receptors: G-protein activation and K+ channel modulation in transfected cells.
2008 May
Gateways to clinical trials.
2009 May
A new strategy for antidepressant prescription.
2010
Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.
2010
Dysfunctional women remain unsexed.
2010 Aug
Management of hypoactive sexual desire disorder in women: current and emerging therapies.
2010 Aug 9
[Normality of the female libido? (2)].
2010 Jul 14
Drug for low sexual desire carries significant harms, FDA advisers find.
2010 Jul 7
Flibanserin, a drug intended for treatment of hypoactive sexual desire disorder in pre-menopausal women, affects spontaneous motor activity and brain neurochemistry in female rats.
2010 Jun
[Normality of the female libido (1)].
2010 Jun 30
Involvement of serotonin receptor subtypes in the antidepressant-like effect of TRIM in the rat forced swimming test.
2010 May
Acute and repeated flibanserin administration in female rats modulates monoamines differentially across brain areas: a microdialysis study.
2010 May
FDA advisers to assess drug for low sexual desire in women.
2010 May 25
Consultation corner. The latest on female sexual health.
2010 Nov
Flibanserin: initial evidence of efficacy on sexual dysfunction, in patients with major depressive disorder.
2010 Oct
Boehringer Ingelheim withdraws libido drug for women.
2010 Oct 12
[The abandonment of the development of flibanserin].
2010 Oct 27
Do drugs have a role in turning indifference into passion?
2010 Oct 5
Flibanserin: a potential treatment for Hypoactive Sexual Desire Disorder in premenopausal women.
2010 Sep
Predicting in vivo absorption behavior of oral modified release dosage forms containing pH-dependent poorly soluble drugs using a novel pH-adjusted biphasic in vitro dissolution test.
2010 Sep
[When women complain about lacking libido. The problem with the desire].
2010 Sep 2
Mechanism of action of flibanserin, a multifunctional serotonin agonist and antagonist (MSAA), in hypoactive sexual desire disorder.
2015 Feb
Flibanserin: First Global Approval.
2015 Oct
Patents

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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:38:37 UTC 2019
Edited
by admin
on Mon Oct 21 21:38:37 UTC 2019
Record UNII
37JK4STR6Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLIBANSERIN
DASH   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
1,3-DIHYDRO-1-(2-(4-(3-(TRIFLUOROMETHYL)PHENYL)-1-PIPERAZINYL)ETHYL)-2H-BENZIMIDAZOL-2-ONE
Systematic Name English
BIMT 17 BS
Code English
1-(2-(4-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)-1-PIPERAZINYL)ETHYL)-2-BENZIMIDAZOLINONE
Systematic Name English
BIMT-17-BS
Code English
BIMT 17
Code English
ADDYI
Brand Name English
FLIBANSERIN [INN]
Common Name English
FLIBANSERIN [MART.]
Common Name English
FLIBANSERIN [USAN]
Common Name English
BIMT-17
Code English
ECTRIS
Brand Name English
FLIBANSERIN [WHO-DD]
Common Name English
FLIBANSERIN [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC G02CX02
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
NCI_THESAURUS C66885
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
Code System Code Type Description
MERCK INDEX
M5402
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C80769
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
IUPHAR
8182
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
ChEMBL
CHEMBL231068
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
RXCUI
1665509
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY RxNorm
CAS
167933-07-5
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
MESH
C098107
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
DRUG BANK
DB04908
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
NDF-RT
N0000185503
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
PUBCHEM
6918248
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
INN
7512
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
WIKIPEDIA
FLIBANSERIN
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
EPA CompTox
167933-07-5
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
EVMPD
SUB07644MIG
Created by admin on Mon Oct 21 21:38:37 UTC 2019 , Edited by admin on Mon Oct 21 21:38:37 UTC 2019
PRIMARY
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SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
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BINDER->LIGAND
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

ORAL BIOAVAILABILITY PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION