Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H20N2.ClH |
Molecular Weight | 264.794 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12CCC[C@]1([H])C3=C4N(C2)CCNCC4=CC=C3
InChI
InChIKey=PYPPENBDXAWXJC-QNTKWALQSA-N
InChI=1S/C15H20N2.ClH/c1-3-11-9-16-7-8-17-10-12-4-2-5-13(12)14(6-1)15(11)17;/h1,3,6,12-13,16H,2,4-5,7-10H2;1H/t12-,13-;/m0./s1
Molecular Formula | C15H20N2 |
Molecular Weight | 228.3327 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Vabicaserin is a 5-hydroxytryptamine 2C (5-HT2C) receptor-selective agonist with an EC50 of 8 nM. Pfizer was developing vabicaserin, an oral serotonin (5-HT)2C receptor agonist, for the treatment of schizophrenia and bipolar disorder. Vabicaserin decreases nucleus accumbens extracellular dopamine levels in rats, without affecting striatal dopamine, indicating mesolimbic selectivity. Vabicaserin had been in phase II clinical trials for the treatment of schizophrenia. However, research of Vabicaserin for the treatment schizophrenia and obesity was discontinued.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Characterization of vabicaserin (SCA-136), a selective 5-hydroxytryptamine 2C receptor agonist. | 2011 Jun |
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Asymmetric synthesis of vabicaserin via oxidative multicomponent annulation and asymmetric hydrogenation of a 3,4-substituted quinolinium salt. | 2013 Jun 21 |
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Prediction of Efficacy of Vabicaserin, a 5-HT2C Agonist, for the Treatment of Schizophrenia Using a Quantitative Systems Pharmacology Model. | 2014 Apr 23 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24613032
Acute schizophrenia: Vabicaserin 200 or 400 mg/day. Vabicaserin demonstrated efficacy on primary and secondary endpoints at 200 mg/day, but not at 400 mg/day which showed a trend for efficacy. The 200 mg/day vabicaserin group achieved proof of concept using central ratings. Both vabicaserin doses were well tolerated with no significant safety signals and no weight gain.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21402690
Vabicaserin displaces 125I-(2,5-dimethoxy)phenylisopropylamine binding from human 5-HT2C receptor sites in Chinese hamster ovary cell membranes with a Ki value of 3 nM and is >50-fold selective over a number of serotonergic, noradrenergic, and dopaminergic receptors. Binding affinity determined for the human 5-HT2B receptor subtype using [3H]5HT is 14 nM. Vabicaserin is a potent and full agonist (EC50, 8 nM; Emax, 100%) in stimulating 5-HT2C receptor-coupled calcium mobilization and exhibits 5-HT2A receptor antagonism and 5-HT2B antagonist or partial agonist activity in transfected cells, depending on the level of receptor expression. Vabicaserin exhibits lower affinity at the 5-HT2C antagonist binding site (22 nM) labeled with [3H]mesulergine. Additional binding studies indicate that Vabicaserin possesses affinity for the 5-HT2B and 5-HT1A receptors with Ki values of 14 and 112 nM, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:43:18 UTC 2023
by
admin
on
Fri Dec 15 15:43:18 UTC 2023
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Record UNII |
2759C7222C
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Record Status |
Validated (UNII)
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Record Version |
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C47794
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ACTIVE MOIETY |