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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.31 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
5.01 μg/kg/min single, intravenous
VOLINANSERIN plasma
Rattus norvegicus

PubMed

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
Record UNII
EW71EE171J
Record Status Validated (UNII)
Record Version