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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
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 sarizotan on the corticostriatal glutamate pathways.
2005 Dec 1
Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia.
2005 Sep
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
In vivo occupancy of dopamine D2 receptors by antipsychotic drugs and novel compounds in the mouse striatum and olfactory tubercles.
2006 Sep
The novel antidyskinetic drug sarizotan elicits different functional responses at human D2-like dopamine receptors.
2006 Sep
Sarizotan as a treatment for dyskinesias in Parkinson's disease: a double-blind placebo-controlled trial.
2007 Jan 15
Differential agonist and inverse agonist profile of antipsychotics at D2L receptors coupled to GIRK potassium channels.
2007 Mar
Investigation of the impact of sarizotan on the pharmacokinetics of levodopa.
2007 Oct
Placebo influences on dyskinesia in Parkinson's disease.
2008 Apr 15
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

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
PRIMARY
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
PRIMARY
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
PRIMARY