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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Serotonin 5-HT1A agonist improves motor complications in rodent and primate parkinsonian models. | 2001 Nov 27 |
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Contribution of the serotonin 5-HT1A receptor agonism of 8-OH-DPAT and EMD 128130 to the regulation of haloperidol-induced muscle rigidity in rats. | 2003 Dec |
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Gateways to clinical trials. | 2003 May |
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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 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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Differential agonist and inverse agonist profile of antipsychotics at D2L receptors coupled to GIRK potassium channels. | 2007 Mar |
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Investigation of the impact of sarizotan on the pharmacokinetics of levodopa. | 2007 Oct |
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Antipsychotics differ in their ability to internalise human dopamine D2S and human serotonin 5-HT1A receptors in HEK293 cells. | 2008 Feb 26 |
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Low doses of sarizotan reduce dyskinesias and maintain antiparkinsonian efficacy of L-Dopa in parkinsonian monkeys. | 2009 Jul |
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Identification of N-propylnoraporphin-11-yl 5-(1,2-dithiolan-3-yl)pentanoate as a new anti-Parkinson's agent possessing a dopamine D2 and serotonin 5-HT1A dual-agonist profile. | 2011 Jul 14 |
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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Fri Dec 15 16:01:11 GMT 2023
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Fri Dec 15 16:01:11 GMT 2023
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Record UNII |
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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