VOLINANSERIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28FNO3
Molecular Weight	373.461
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C(=CC=C1)[C@H](O)C2CCN(CCC3=CC=C(F)C=C3)CC2

InChI

InChIKey=HXTGXYRHXAGCFP-OAQYLSRUSA-N

InChI=1S/C22H28FNO3/c1-26-20-5-3-4-19(22(20)27-2)21(25)17-11-14-24(15-12-17)13-10-16-6-8-18(23)9-7-16/h3-9,17,21,25H,10-15H2,1-2H3/t21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H28FNO3
Molecular Weight	373.461
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/MDL100907.pdf | https://www.ncbi.nlm.nih.gov/pubmed/11527004

Volinanserin (MDL-100,907) is a highly selective 5-HT2A receptor antagonist. It is widely used in scientific research to investigate the function of the 5-HT2A receptor. Volinanserin is also being trialed as a potential antipsychotic, antidepressant and treatment for insomnia. Volinanserin (M-100907) was in phase III trials for chronic schizophrenia. In August 1999, development was discontinued for acute schizophrenia (schizoaffective disorder) on the basis of poor results. M-100907 is also active in animal models involving blockade of NMDA glutamatergic channel receptors, an effect known to resemble some behavioral symptoms of schizophrenia in man. M-100907 is also claimed in other patents for the treatment of thromboembolic disorders, for the treatment of various developmental neurological disorders such as autism and attention deficit hyperactivity disorder.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8857599 \| https://www.ncbi.nlm.nih.gov/pubmed/7957607	Antagonist 2778		0.31 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/MDL100907.pdf	Primary		Phase III 656	Unknown Approved Use Unknown
Insomnia 108 Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/MDL100907.pdf http://adisinsight.springer.com/drugs/800001847	Primary		Phase III 656	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY103825	https://www.001chemical.com/chem/search?q=DY103825
1PlusChem LLC	1P001B5R	https://www.1pchem.com/search?query=1P001B5R
AChemBlock	G-6605	http://www.achemblock.com/catalogsearch/result/?q=G-6605
AK Scientific	3918AL	https://aksci.com/item_detail.php?cat=3918AL
Aceschem	ACF023148	https://www.aceschem.com/catalog/search.do?q=ACF023148
Alfa Chemistry	139290-69-0	http://www.alfa-chemistry.com/search.aspx?q=139290-69-0
Angene	AGN-PC-0PO4IK	http://www.angenechemical.com/productshow/AGN-PC-0PO4IK.html
AstaTech	41200	http://astatechinc.com/CPSResult.php?CRNO=41200
AstaTech	44069	http://astatechinc.com/CPSResult.php?CRNO=44069
Axon MedChem	1103	https://www.axonmedchem.com/product/1103
Axon MedChem	1104	https://www.axonmedchem.com/product/1104
BLD Pharm	BD448327	http://www.bldpharm.com/search/Search.html?keyword=BD448327
BLD Pharm	BD47118	http://www.bldpharm.com/search/Search.html?keyword=BD47118
BOC Sciences	139290-65-6	http://www.bocsci.com/description.asp?cas=139290-65-6
Cayman Chemical	15936	http://www.caymanchem.com/app/template/Product.vm/catalog/15936
Chem Scene	CS-0003646	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0003646
Fluorochem	436152	http://www.fluorochem.co.uk/Products/Product?code=436152
KeyOrganics	AS-35103	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35103
Lab Network	LN01315124	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01315124
Lab Network	LN02195775	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02195775
Matrix Scientific	122661	http://www.matrixscientific.com/122661.html
MedChem Express	HY-14940	https://www.medchemexpress.com/search.html?q=HY-14940&ft=&fa=&fp=
MolPort	MolPort-003-850-862	https://www.molport.com/shop/molecule-link/MolPort-003-850-862
MolPort	MolPort-039-331-873	https://www.molport.com/shop/molecule-link/MolPort-039-331-873
Molcore	MC103825	http://www.molcore.com/CatMC103825.html
Molnova	M11635	https://www.molnova.com/en/serch-list.html?keywords=M11635
MuseChem	R008181	https://www.musechem.com/product/R008181.html
Synthonix	11875	https://synthonix.com/catalogsearch/result/?q=11875
TargetMol	T5389	https://www.targetmol.com/search?keyword=T5389
Tetrahedron	TS80113	http://www.thsci.com/search.do?q=TS80113
Tocris	4173	https://www.tocris.com/search.php?Type=QuickSearch&Value=4173
Toronto Research Chemicals	V755000	https://www.trc-canada.com/product-detail/?CatNum=V755000
Toronto Research Chemicals	V755003	https://www.trc-canada.com/product-detail/?CatNum=V755003
Wonderchem	WD05682	http://www.wonder-chem.com/search.html?text=WD05682
eMolecules	275096801	https://orderbb.emolecules.com/search/#?query=275096801
eMolecules	27524720	https://orderbb.emolecules.com/search/#?query=27524720
eMolecules	300464422	https://orderbb.emolecules.com/search/#?query=300464422
eMolecules	300464678	https://orderbb.emolecules.com/search/#?query=300464678
eMolecules	36366904	https://orderbb.emolecules.com/search/#?query=36366904
eNovation Chemicals	D499431	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D499431&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-6810139651	https://mcule.com/MCULE-6810139651/

PubMed

Title	Date	PubMed
		252159862
Attenuation of haloperidol-induced catalepsy by a 5-HT2C receptor antagonist.	1999 Feb	10188965
Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists.	2001 Oct	11562430
Regulation of septo-hippocampal activity by 5-hydroxytryptamine(2C) receptors.	2003 Aug	12734389
Evaluation of the ocular hypotensive response of serotonin 5-HT1A and 5-HT2 receptor ligands in conscious ocular hypertensive cynomolgus monkeys.	2003 Jul	12676887
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.	2004 Aug	15322733
Effects of the serotonin 5-HT2A and 5-HT2C receptor ligands on the discriminative stimulus effects of nicotine in rats.	2007 Oct 1	17617403
5-HT(2A) inverse-agonists for the treatment of insomnia.	2008	18673166

Patents

Sample Use Guides

In Vivo Use Guide

Schizophrenia treatment: an oral dose of 20 mg per day ensures adequate 5HT(2A) receptor occupancy for clinical proof of concept.

Route of Administration: Oral

In Vitro Use Guide

The selective 5-HT(2A) receptor antagonist Volinanserin (0.05 uM), strongly enhanced the reversal of amphetamine-induced inhibition by (-)sulpiride in A10, but its effectiveness was much smaller in A9 dopamine neurons in in rat midbrain slices.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:17:13 GMT 2023` Edited by `admin` on `Fri Dec 15 17:17:13 GMT 2023`
Record UNII	EW71EE171J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VOLINANSERIN

Official Name

English

volinanserin [INN]

Common Name

English

4-PIPERIDINEMETHANOL, .ALPHA.-(2,3-DIMETHOXYPHENYL)-1-(2-(4-FLUOROPHENYL)ETHYL)-, (.ALPHA.R)-

Systematic Name

English

(R)-(2,3-DIMETHOXYPHENYL)(1-(2-(4-FLUOROPHENYL)ETHYL)PIPERIDIN-4-YL)METHANOL

Systematic Name

English

MDL-100.907

Code

English

MDL100.907

Code

English

MDL-100907

Code

English

M-100907

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C66885