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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H21FN2O.ClH
Molecular Weight 384.874
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARIZOTAN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=QDLVYMYXOLGZOD-ZMBIFBSDSA-N
InChI=1S/C22H21FN2O.ClH/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;1H/t21-;/m1./s1

HIDE SMILES / InChI
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
Gateways to clinical trials.
2003 May
Drugs in development for Parkinson's disease.
2004 Jul
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
Effects of serotonin 5-HT1A agonist in advanced Parkinson's disease.
2005 Aug
Changes in sleep electroencephalogram and nocturnal hormone secretion after administration of the antidyskinetic agent sarizotan in healthy young male volunteers.
2005 Jul
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
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
[Dyskinesia in Parkinson's disease--major clinical features, aetiology, therapy].
2007 Jul
Putative antipsychotics with pronounced agonism at serotonin 5-HT1A and partial agonist activity at dopamine D2 receptors disrupt basal PPI of the startle reflex in rats.
2007 Jul
Investigation of the impact of sarizotan on the pharmacokinetics of levodopa.
2007 Oct
Low doses of sarizotan reduce dyskinesias and maintain antiparkinsonian efficacy of L-Dopa in parkinsonian monkeys.
2009 Jul
Patents

Patents

Sample Use Guides

Subjects will receive sarizotan 1 milligram orally twice daily for 24 weeks.
Route of Administration: Oral
Name Type Language
SARIZOTAN HYDROCHLORIDE
USAN  
USAN  
Official Name English
EMD-128130
Code English
3-PYRIDINEMETHANAMINE, N-(((2R)-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-YL)METHYL)-5-(4-FLUOROPHENYL)-, MONOHYDROCHLORIDE
Common Name English
(-)-N-(((2R)-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-YL)METHYL)-5-(4-FLUOROPHENYL)PYRIDINE-3-YL)METHANAMINE MONOHYDROCHLORIDE
Common Name English
SARIZOTAN HYDROCHLORIDE [USAN]
Common Name English
SARIZOTAN HCL
Common Name English
EMD 128130
Code English
3-PYRIDINEMETHANAMINE, N-(((2R)-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-YL)METHYL)-5-(4-FLUOROPHENYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
EU-Orphan Drug EU/3/15/1531
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
Code System Code Type Description
MESH
C443959
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
PRIMARY
FDA UNII
5P71E6YO9H
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
PRIMARY
NCI_THESAURUS
C76654
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
PRIMARY
USAN
RR-123
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL220808
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
PRIMARY
SMS_ID
100000084888
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
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CAS
195068-07-6
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
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EPA CompTox
DTXSID60173163
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
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EVMPD
SUB21592
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
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PUBCHEM
6918387
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
PRIMARY
DRUG BANK
DBSALT002015
Created by admin on Fri Dec 15 17:20:49 GMT 2023 , Edited by admin on Fri Dec 15 17:20:49 GMT 2023
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