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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H21FN2O.2ClH
Molecular Weight 421.335
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARIZOTAN DIHYDROCHLORIDE

SMILES

Cl.Cl.FC1=CC=C(C=C1)C2=CN=CC(CNC[C@H]3CCC4=C(O3)C=CC=C4)=C2

InChI

InChIKey=ANXOJXYTTDGHAJ-GHVWMZMZSA-N
InChI=1S/C22H21FN2O.2ClH/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;2*1H/t21-;;/m1../s1

HIDE SMILES / InChI

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Changes in sleep electroencephalogram and nocturnal hormone secretion after administration of the antidyskinetic agent sarizotan in healthy young male volunteers.
2005 Jul
In 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated primates, the selective 5-hydroxytryptamine 1a agonist (R)-(+)-8-OHDPAT inhibits levodopa-induced dyskinesia but only with\ increased motor disability.
2006 Dec
[Dyskinesia in Parkinson's disease--major clinical features, aetiology, therapy].
2007 Jul
Alterations in mGluR5 expression and signaling in Lewy body disease and in transgenic models of alpha-synucleinopathy--implications for excitotoxicity.
2010 Nov 16
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

Patents

Sample Use Guides

Subjects will receive sarizotan 1 milligram orally twice daily for 24 weeks.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:11:03 UTC 2023
Edited
by admin
on Sat Dec 16 11:11:03 UTC 2023
Record UNII
4D56ANR2VD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SARIZOTAN DIHYDROCHLORIDE
MI  
Common Name English
3-PYRIDINEMETHANAMINE, N-(((2R)-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-YL)METHYL)-5-(4-FLUOROPHENYL)-, DIHYDROCHLORIDE
Systematic Name English
(-)-N-(((2R)-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-YL)METHYL)-5-(4-FLUOROPHENYL)-3-PYRIDINEMETHANAMINE DIHYDROCHLORIDE
Systematic Name English
SARIZOTAN DIHYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
FDA UNII
4D56ANR2VD
Created by admin on Sat Dec 16 11:11:03 UTC 2023 , Edited by admin on Sat Dec 16 11:11:03 UTC 2023
PRIMARY
MERCK INDEX
m9782
Created by admin on Sat Dec 16 11:11:03 UTC 2023 , Edited by admin on Sat Dec 16 11:11:03 UTC 2023
PRIMARY Merck Index
CAS
177976-12-4
Created by admin on Sat Dec 16 11:11:03 UTC 2023 , Edited by admin on Sat Dec 16 11:11:03 UTC 2023
PRIMARY
PUBCHEM
68742912
Created by admin on Sat Dec 16 11:11:03 UTC 2023 , Edited by admin on Sat Dec 16 11:11:03 UTC 2023
PRIMARY
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