F-15599

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H21ClF2N4O
Molecular Weight	394.846
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CN=C(CNCC2(F)CCN(CC2)C(=O)C3=CC=C(F)C(Cl)=C3)N=C1

InChI

InChIKey=WAAXKNFGOFTGLP-UHFFFAOYSA-N

InChI=1S/C19H21ClF2N4O/c1-13-9-24-17(25-10-13)11-23-12-19(22)4-6-26(7-5-19)18(27)14-2-3-16(21)15(20)8-14/h2-3,8-10,23H,4-7,11-12H2,1H3

HIDE SMILES / InChI

Molecular Formula	C19H21ClF2N4O
Molecular Weight	394.846
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://rettsyndrome.wordpress.com/2015/06/24/rsrt-awards-530000-to-neurolixis-for-clinical-development-of-nlx-101/ | https://www.ncbi.nlm.nih.gov/pubmed/20059805 | https://www.ncbi.nlm.nih.gov/pubmed/19789870

F-15599 is a novel agonist with high selectivity and efficacy at serotonin 5-HT(1A) receptors. In signal transduction, electrophysiological and neurochemical tests, F-15599 preferentially activates post-synaptic 5-HT(1A)Rs in rat frontal cortex. Such a profile may translate to an improved profile of therapeutic activity for mood disorders. [(18)F]F-15599 is a radiofluorinated agonist presenting interesting characteristics for probing in vitro and in vivo the high-affinity states of the 5-HT(1A) receptors. The Rett Syndrome Research Trust awarded a grant to Neurolixis to advance F-15599 to clinical development.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 1A 54 Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26694810 \| https://www.ncbi.nlm.nih.gov/pubmed/20059805	Agonist 2678		3.4 nM [Ki]

PubMed

Title	Date	PubMed
High-efficacy 5-HT1A agonists for antidepressant treatment: a renewed opportunity.	2007 Oct 4	17803293
Signal transduction and functional selectivity of F15599, a preferential post-synaptic 5-HT1A receptor agonist.	2009 Jan	19154445
Preferential in vivo action of F15599, a novel 5-HT(1A) receptor agonist, at postsynaptic 5-HT(1A) receptors.	2010 Aug	20649591
[18F]F15599, a novel 5-HT1A receptor agonist, as a radioligand for PET neuroimaging.	2010 Mar	19789870
F15599, a highly selective post-synaptic 5-HT(1A) receptor agonist: in-vivo profile in behavioural models of antidepressant and serotonergic activity.	2010 Nov	20059805
F15599, a preferential post-synaptic 5-HT1A receptor agonist: activity in models of cognition in comparison with reference 5-HT1A receptor agonists.	2010 Sep	20488670

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:05:09 UTC 2023` Edited by `admin` on `Sat Dec 16 11:05:09 UTC 2023`
Record UNII	83481Y1YCX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

F-15599

Common Name

English

3-CHLORO-4-FLUOROPHENYL-(4-FLUORO-4-(((5-METHYLPYRIMIDIN-2-YLMETHYL)AMINO)METHYL)PIPERIDIN-1YL)METHANONE

Systematic Name

English

4-PIPERIDINEMETHANAMINE, 1-(3-CHLORO-4-FLUOROBENZOYL)-4-FLUORO-N-((5-METHYL-2-PYRIMIDINYL)METHYL)-

Systematic Name

English

F-15,599

Code

English

(3-CHLORO-4-FLUOROPHENYL)-(4-FLUORO-4-(((5-METHYLPYRIMIDIN-2-YLMETHYL)AMINO)METHYL)PIPERIDIN-1-YL)METHANONE

Systematic Name

English

NLX-101

Common Name

English

METHANONE, (3-CHLORO-4-FLUOROPHENYL)(4-FLUORO-4-((((5-METHYL-2-PYRIMIDINYL)METHYL)AMINO)METHYL)-1-PIPERIDINYL)-

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

410613