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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=CC=CC=C4O3)=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
Evaluation of EMD 128 130 occupancy of the 5-HT1A and the D2 receptor: a human PET study with [11C]WAY-100635 and [11C]raclopride.
2002 Sep
Gateways to clinical trials.
2003 May
Effects of sarizotan on the corticostriatal glutamate pathways.
2005 Dec 1
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
In vivo occupancy of dopamine D2 receptors by antipsychotic drugs and novel compounds in the mouse striatum and olfactory tubercles.
2006 Sep
Current approaches to the treatment of Parkinson's disease.
2008 Aug
Low doses of sarizotan reduce dyskinesias and maintain antiparkinsonian efficacy of L-Dopa in parkinsonian monkeys.
2009 Jul
Local administration of sarizotan into the subthalamic nucleus attenuates levodopa-induced dyskinesias in 6-OHDA-lesioned rats.
2009 Jun
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
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 Mon Mar 31 23:41:02 GMT 2025
Edited
by admin
on Mon Mar 31 23:41:02 GMT 2025
Record UNII
4D56ANR2VD
Record Status Validated (UNII)
Record Version
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Name Type Language
SARIZOTAN DIHYDROCHLORIDE [MI]
Preferred Name English
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
Code System Code Type Description
FDA UNII
4D56ANR2VD
Created by admin on Mon Mar 31 23:41:02 GMT 2025 , Edited by admin on Mon Mar 31 23:41:02 GMT 2025
PRIMARY
MERCK INDEX
m9782
Created by admin on Mon Mar 31 23:41:02 GMT 2025 , Edited by admin on Mon Mar 31 23:41:02 GMT 2025
PRIMARY Merck Index
CAS
177976-12-4
Created by admin on Mon Mar 31 23:41:02 GMT 2025 , Edited by admin on Mon Mar 31 23:41:02 GMT 2025
PRIMARY
PUBCHEM
68742912
Created by admin on Mon Mar 31 23:41:02 GMT 2025 , Edited by admin on Mon Mar 31 23:41:02 GMT 2025
PRIMARY
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ACTIVE MOIETY