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
Investigation of sarizotan's impact on the pharmacokinetics of probe drugs for major cytochrome P450 isoenzymes: a combined cocktail trial.	2006 Apr	16525816
Translation of nondopaminergic treatments for levodopa-induced dyskinesia from MPTP-lesioned nonhuman primates to phase IIa clinical studies: keys to success and roads to failure.	2006 Oct	16874752
In vivo occupancy of dopamine D2 receptors by antipsychotic drugs and novel compounds in the mouse striatum and olfactory tubercles.	2006 Sep	16947046
The novel antidyskinetic drug sarizotan elicits different functional responses at human D2-like dopamine receptors.	2006 Sep	16844149
Sarizotan as a treatment for dyskinesias in Parkinson's disease: a double-blind placebo-controlled trial.	2007 Jan 15	17094088
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
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	20219851
Alterations in mGluR5 expression and signaling in Lewy body disease and in transgenic models of alpha-synucleinopathy--implications for excitotoxicity.	2010 Nov 16	21103359
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	21591752

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 UTC 2023` Edited by `admin` on `Fri Dec 15 17:20:49 UTC 2023`
Record UNII	5P71E6YO9H
Record Status	`Validated (UNII)`
Record Version

Download

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