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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 of VOLINANSERIN

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

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.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
2004 Aug
Effects of the serotonin 5-HT2A and 5-HT2C receptor ligands on the discriminative stimulus effects of nicotine in rats.
2007 Oct 1
5-HT(2A) inverse-agonists for the treatment of insomnia.
2008
Patents

Sample Use Guides

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
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 UTC 2023
Edited
by admin
on Fri Dec 15 17:17:13 UTC 2023
Record UNII
EW71EE171J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VOLINANSERIN
INN  
INN  
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
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
Code System Code Type Description
CAS
139290-65-6
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
NCI_THESAURUS
C95220
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID6047363
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
FDA UNII
EW71EE171J
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
PUBCHEM
5311271
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
WIKIPEDIA
Volinanserin
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
SMS_ID
300000034460
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
INN
8767
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL74355
Created by admin on Fri Dec 15 17:17:13 UTC 2023 , Edited by admin on Fri Dec 15 17:17:13 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
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LABELED -> NON-LABELED
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ACTIVE MOIETY