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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H21FN2O
Molecular Weight 348.4133
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARIZOTAN

SMILES

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

InChI

InChIKey=HKFMQJUJWSFOLY-OAQYLSRUSA-N
InChI=1S/C22H21FN2O/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/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
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
Multicenter, open-label, trial of sarizotan in Parkinson disease patients with levodopa-induced dyskinesias (the SPLENDID Study).
2004 Mar-Apr
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
Investigation of sarizotan's impact on the pharmacokinetics of probe drugs for major cytochrome P450 isoenzymes: a combined cocktail trial.
2006 Apr
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
Current approaches to the treatment of Parkinson's disease.
2008 Aug
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
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
Name Type Language
SARIZOTAN
INN   MI   WHO-DD  
INN  
Official Name English
3-PYRIDINEMETHANAMINE, 5-(4-FLUOROPHENYL)-N-(((2R)-3,4,4A,8A-TETRAHYDRO-2H-1-BENZOPYRAN-2-YL)METHYL)-
Common Name English
SARIZOTAN [MI]
Common Name English
EMD-77697
Code English
3-PYRIDINEMETHANAMINE, N-(((2R)-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-YL)METHYL)-5-(4-FLUOROPHENYL)-
Systematic Name English
Sarizotan [WHO-DD]
Common Name English
sarizotan [INN]
Common Name English
1-(5-(4-FLUOROPHENYL)PYRIDIN-3-YL)-N-((2R)-3,4,4A,8A-TETRAHYDRO-2H-CHROMEN-2-YLMETHYL)METHANAMINE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 484015
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
NCI_THESAURUS C1509
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL220808
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
PRIMARY
INN
7748
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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NCI_THESAURUS
C77567
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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SMS_ID
100000084927
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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CAS
351862-32-3
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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MESH
C443959
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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DRUG BANK
DB06454
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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WIKIPEDIA
Sarizotan
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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PUBCHEM
6918388
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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MERCK INDEX
m9782
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
PRIMARY Merck Index
FDA UNII
467LU0UCUW
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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EPA CompTox
DTXSID80956632
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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EVMPD
SUB04329MIG
Created by admin on Fri Dec 15 16:01:11 GMT 2023 , Edited by admin on Fri Dec 15 16:01:11 GMT 2023
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