FANANSERIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H24FN3O2S
Molecular Weight	425.519
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(C=C1)N2CCN(CCCN3C4=CC=CC5=C4C(=CC=C5)S3(=O)=O)CC2

InChI

InChIKey=VGIGHGMPMUCLIQ-UHFFFAOYSA-N

InChI=1S/C23H24FN3O2S/c24-19-8-10-20(11-9-19)26-16-14-25(15-17-26)12-3-13-27-21-6-1-4-18-5-2-7-22(23(18)21)30(27,28)29/h1-2,4-11H,3,12-17H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10513457 | https://www.ncbi.nlm.nih.gov/pubmed/1596688 | https://www.ncbi.nlm.nih.gov/pubmed/16168646

Fananserin is a potential antipsychotic compound with a high affinity for both D4 and 5-HT2A receptors, and negligible affinity for D2 receptors. Fananserin has been researched for the treatment of schizophrenia. Fananserin was the first selective D4/5-HT2A antagonist to undergo clinical trials for schizophrenia. It has a high affinity for D4 (Ki 2.9 nM) and 5-HT2A (Ki 0.37 nM) receptors and is over 100-fold selective versus H1, a1 adrenergic, 5-HT1A and D2 dopamine receptors. Development of this compound was halted following phase II clinical trials due to lack of efficacy.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D4 receptor 71 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10080558	Antagonist 2778		2.93 nM [Ki]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1596688 \| https://www.ncbi.nlm.nih.gov/pubmed/8472747 \| https://www.ncbi.nlm.nih.gov/pubmed/1908521	Antagonist 2778		0.37 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10513457 http://adisinsight.springer.com/drugs/800001227 https://www.ncbi.nlm.nih.gov/pubmed/10080558	Primary	Phase I 428	Unknown Approved Use Unknown
Anxiety 267 Sources: http://adisinsight.springer.com/drugs/800001227 http://en.pharmacodia.com/web/drug/1_12626.html	Primary	Phase II 1132	Unknown Approved Use Unknown
Major depressive disorder 173 Sources: http://adisinsight.springer.com/drugs/800001227 http://en.pharmacodia.com/web/drug/1_12626.html	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P000XOX	https://www.1pchem.com/search?query=1P000XOX
ApexBio Technology	B7136	https://www.apexbt.com/catalogsearch/result/?q=B7136
BOC Sciences	127625-29-0	http://www.bocsci.com/description.asp?cas=127625-29-0
Chem Scene	CS-0024310	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0024310
KeyOrganics	AS-74345	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74345
MedChem Express	HY-103104	https://www.medchemexpress.com/search.html?q=HY-103104&ft=&fa=&fp=
MolPort	MolPort-023-276-525	https://www.molport.com/shop/molecule-link/MolPort-023-276-525
MuseChem	M106137	https://www.musechem.com/product/M106137.html
Tocris	2645	https://www.tocris.com/search.php?Type=QuickSearch&Value=2645
Toronto Research Chemicals	E932533	https://www.trc-canada.com/product-detail/?CatNum=E932533
Toronto Research Chemicals	F102368	https://www.trc-canada.com/product-detail/?CatNum=F102368
Wonderchem	WD051FY	http://www.wonder-chem.com/search.html?text=WD051FY
eMolecules	8793859	https://orderbb.emolecules.com/search/#?query=8793859

PubMed

Title	Date	PubMed
Autoradiographic studies of RP 62203, a potent 5-HT2 receptor antagonist. Pharmacological characterization of [3H]RP 62203 binding in the rat brain.	1993 Mar 16	8472747
[Thermodynamics of drug polymorphism: domains and stability hierarchy by pressure temperature diagram. Application to the tetramorphism of fananserine].	2002 May	12050598
Molecular mobility in glass forming fananserine: a dielectric, NMR, and TMDSC investigation.	2006 Apr	16575499
Ordering and disordering of molecular solids upon mechanical milling: the case of fananserine.	2008 Nov	18702119

Patents

Sample Use Guides

In Vivo Use Guide

Treatment of schizophrenia: doses of fananserin reached 250 mg b.i.d. over 28 days, starting with an 8-day escalation.

Route of Administration: Oral

In Vitro Use Guide

In in vitro experiments, RP 62203 (Fananserin) displaced [125I]AMIK from 5-HT2 receptors with an IC50 of 0.21 nM in rat frontal cortex.

Name

Type

Language

FANANSERIN

Official Name

English

FANANSERIN [USAN]

Common Name

English

RP-62203

Code

English

fananserin [INN]

Common Name

English

2H-NAPHTH(1,8-CD)ISOTHIAZOLE, 2-(3-(4-(4-FLUOROPHENYL)-1-PIPERAZINYL)PROPYL)-, 1,1-DIOXIDE

Systematic Name

English

RP 62203

Code

English

2-(3-(4-(P-FLUOROPHENYL)-1-PIPERAZINYL)PROPYL)-2H-NAPHTH(1,8-CD)ISOTHIAZOLE 1,1-DIOXIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885