Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H21FN2O |
Molecular Weight | 348.4133 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
FC1=CC=C(C=C1)C2=CN=CC(CNC[C@H]3CCC4=C(O3)C=CC=C4)=C2
InChI
InChIKey=HKFMQJUJWSFOLY-OAQYLSRUSA-N
InChI=1S/C22H21FN2O/c23-20-8-5-17(6-9-20)19-11-16(12-24-14-19)13-25-15-21-10-7-18-3-1-2-4-22(18)26-21/h1-6,8-9,11-12,14,21,25H,7,10,13,15H2/t21-/m1/s1
Molecular Formula | C22H21FN2O |
Molecular Weight | 348.4133 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Sarizotan (also known as EMD-128,130), a chromane derivative that was developed as a selective 5-HT1A receptor agonist and D2 receptor antagonist. Experiments on animal models have shown that the drug effectively suppressed levodopa-induced dyskinesia in primate and rodent models of Parkinson's disease, and tardive dyskinesia in a rodent model. Sarizotan participated in phase II/III clinical trials in the treatment of dyskinesia associated with the dopaminergic treatment of Parkinson's disease. However, further development for this disease was discontinued by Merk, because phase III did not confirm earlier Phase II findings. On July 14, 2015, Newron Pharmaceuticals, research, and development company focused on the novel central nervous system (CNS) and pain therapies, announced that the U.S. Food and Drug Administration (FDA) has granted Orphan Drug Designation to sarizotan for treatment of Rett syndrome. Besides, the drug now is an ongoing clinical trial phase II/III to investigate its the tolerability and efficacy in reducing respiratory abnormalities in Rett Syndrome.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Sarizotan, a serotonin 5-HT1A receptor agonist and dopamine receptor ligand. 1. Neurochemical profile. | 2004 Feb |
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Drugs in development for Parkinson's disease. | 2004 Jul |
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Effects of serotonin 5-HT1A agonist in advanced Parkinson's disease. | 2005 Aug |
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Effects of sarizotan on the corticostriatal glutamate pathways. | 2005 Dec 1 |
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Contrasting contribution of 5-hydroxytryptamine 1A receptor activation to neurochemical profile of novel antipsychotics: frontocortical dopamine and hippocampal serotonin release in rat brain. | 2005 Oct |
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Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia. | 2005 Sep |
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Investigation of sarizotan's impact on the pharmacokinetics of probe drugs for major cytochrome P450 isoenzymes: a combined cocktail trial. | 2006 Apr |
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The effect of chronic administration of sarizotan, 5-HT1A agonist/D3/D4 ligand, on haloperidol-induced repetitive jaw movements in rat model of tardive dyskinesia. | 2006 Mar |
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Antipsychotic-like vs cataleptogenic actions in mice of novel antipsychotics having D2 antagonist and 5-HT1A agonist properties. | 2006 Sep |
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Investigation of the impact of sarizotan on the pharmacokinetics of levodopa. | 2007 Oct |
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Alterations in mGluR5 expression and signaling in Lewy body disease and in transgenic models of alpha-synucleinopathy--implications for excitotoxicity. | 2010 Nov 16 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00105508
Subjects will receive sarizotan 1 milligram orally twice daily for 24 weeks.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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467LU0UCUW
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FDA ORPHAN DRUG |
484015
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NCI_THESAURUS |
C1509
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> AGONIST |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
to be confirm by NMR
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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