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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H21FN2O
Molecular Weight 348.4142
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARIZOTAN

SMILES

c1ccc2c(c1)CC[C@]([H])(CNCc3cc(cnc3)-c4ccc(cc4)F)O2

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

Molecular Formula C22H21FN2O
Molecular Weight 348.4142
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Contribution of the serotonin 5-HT1A receptor agonism of 8-OH-DPAT and EMD 128130 to the regulation of haloperidol-induced muscle rigidity in rats.
2003 Dec
Gateways to clinical trials.
2003 May
Sarizotan, a serotonin 5-HT1A receptor agonist and dopamine receptor ligand. 1. Neurochemical profile.
2004 Feb
Drugs in development for Parkinson's disease.
2004 Jul
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
Changes in sleep electroencephalogram and nocturnal hormone secretion after administration of the antidyskinetic agent sarizotan in healthy young male volunteers.
2005 Jul
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
The novel antidyskinetic drug sarizotan elicits different functional responses at human D2-like dopamine receptors.
2006 Sep
[Dyskinesia in Parkinson's disease--major clinical features, aetiology, therapy].
2007 Jul
Differential agonist and inverse agonist profile of antipsychotics at D2L receptors coupled to GIRK potassium channels.
2007 Mar
Antipsychotics differ in their ability to internalise human dopamine D2S and human serotonin 5-HT1A receptors in HEK293 cells.
2008 Feb 26
Low doses of sarizotan reduce dyskinesias and maintain antiparkinsonian efficacy of L-Dopa in parkinsonian monkeys.
2009 Jul
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:53:54 UTC 2021
Edited
by admin
on Sat Jun 26 11:53:54 UTC 2021
Record UNII
467LU0UCUW
Record Status Validated (UNII)
Record Version
  • Download
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 [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
SARIZOTAN [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 484015
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
NCI_THESAURUS C1509
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL220808
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
INN
7748
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
NCI_THESAURUS
C77567
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
CAS
351862-32-3
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
MESH
C443959
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
DRUG BANK
DB06454
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
PUBCHEM
6918388
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
MERCK INDEX
M9782
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY Merck Index
FDA UNII
467LU0UCUW
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
EVMPD
SUB04329MIG
Created by admin on Sat Jun 26 11:53:55 UTC 2021 , Edited by admin on Sat Jun 26 11:53:55 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
METABOLITE -> PARENT
to be confirm by NMR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC