Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H21FN2O |
Molecular Weight | 348.4142 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc2c(c1)CC[C@]([H])(CNCc3cc(cnc3)-c4ccc(cc4)F)O2
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 | 348.4142 |
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 |
---|---|---|
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 |
|
Gateways to clinical trials. | 2003 May |
|
Sarizotan, a serotonin 5-HT1A receptor agonist and dopamine receptor ligand. 1. Neurochemical profile. | 2004 Feb |
|
Drugs in development for Parkinson's disease. | 2004 Jul |
|
Multicenter, open-label, trial of sarizotan in Parkinson disease patients with levodopa-induced dyskinesias (the SPLENDID Study). | 2004 Mar-Apr |
|
Novel antipsychotic agents with 5-HT(1A) agonist properties: role of 5-HT(1A) receptor activation in attenuation of catalepsy induction in rats. | 2005 Aug |
|
Changes in sleep electroencephalogram and nocturnal hormone secretion after administration of the antidyskinetic agent sarizotan in healthy young male volunteers. | 2005 Jul |
|
Translation of nondopaminergic treatments for levodopa-induced dyskinesia from MPTP-lesioned nonhuman primates to phase IIa clinical studies: keys to success and roads to failure. | 2006 Oct |
|
The novel antidyskinetic drug sarizotan elicits different functional responses at human D2-like dopamine receptors. | 2006 Sep |
|
[Dyskinesia in Parkinson's disease--major clinical features, aetiology, therapy]. | 2007 Jul |
|
Differential agonist and inverse agonist profile of antipsychotics at D2L receptors coupled to GIRK potassium channels. | 2007 Mar |
|
Antipsychotics differ in their ability to internalise human dopamine D2S and human serotonin 5-HT1A receptors in HEK293 cells. | 2008 Feb 26 |
|
Low doses of sarizotan reduce dyskinesias and maintain antiparkinsonian efficacy of L-Dopa in parkinsonian monkeys. | 2009 Jul |
|
In vitro characterization of sarizotan metabolism: hepatic clearance, identification and characterization of metabolites, drug-metabolizing enzyme identification, and evaluation of cytochrome p450 inhibition. | 2010 Jun |
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
by
admin
on
Edited
Sat Jun 26 11:53:54 UTC 2021
by
admin
on
Sat Jun 26 11:53:54 UTC 2021
|
Record UNII |
467LU0UCUW
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
FDA ORPHAN DRUG |
484015
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
||
|
NCI_THESAURUS |
C1509
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
CHEMBL220808
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
7748
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
C77567
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
351862-32-3
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
C443959
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
DB06454
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
6918388
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
M9782
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | Merck Index | ||
|
467LU0UCUW
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY | |||
|
SUB04329MIG
Created by
admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT | |||
|
METABOLITE -> PARENT |
MAJOR
|
||
|
METABOLITE -> PARENT |
to be confirm by NMR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Tmax | PHARMACOKINETIC |
|
ORAL ADMINISTRATION |
|
||
Biological Half-life | PHARMACOKINETIC |
|
|
|||