SARIZOTAN HYDROCHLORIDE

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 Search

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

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

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

Description
Sources: https://www.businesswire.com/news/home/20150714005335/en/Newron-Receives-FDA-Orphan-Drug-Designation-Sarizotan | http://www.pharmatimes.com/news/merck_drops_late-stage_parkinsons_drug_996337 | https://clinicaltrials.gov/ct2/show/NCT02790034

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
Sarizotan, a serotonin 5-HT1A receptor agonist and dopamine receptor ligand. 1. Neurochemical profile.	2004 Feb	14767715
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	15996562
Effects of serotonin 5-HT1A agonist in advanced Parkinson's disease.	2005 Aug	15791634
Effects of sarizotan on the corticostriatal glutamate pathways.	2005 Dec 1	16138317
Changes in sleep electroencephalogram and nocturnal hormone secretion after administration of the antidyskinetic agent sarizotan in healthy young male volunteers.	2005 Jul	15717211
Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia.	2005 Sep	15707540
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	16959959
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	16229932
The novel antidyskinetic drug sarizotan elicits different functional responses at human D2-like dopamine receptors.	2006 Sep	16844149
Pharmacokinetics of sarizotan after oral administration of single and repeat doses in healthy subjects.	2007 May	17542349
Placebo influences on dyskinesia in Parkinson's disease.	2008 Apr 15	18175337
Antipsychotics differ in their ability to internalise human dopamine D2S and human serotonin 5-HT1A receptors in HEK293 cells.	2008 Feb 26	18190908

Patents

Sample Use Guides

In Vivo Use Guide

Subjects will receive sarizotan 1 milligram orally twice daily for 24 weeks.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:20:49 GMT 2023` Edited by `admin` on `Fri Dec 15 17:20:49 GMT 2023`
Record UNII	5P71E6YO9H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SARIZOTAN HYDROCHLORIDE

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