This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Sarizotan
Accession Number
DB06454
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • neuroleptic
External IDs
EMD-77697
Product Ingredients
IngredientUNIICASInChI Key
Sarizotan Hydrochloride5P71E6YO9H195068-07-6QDLVYMYXOLGZOD-ZMBIFBSDSA-N
Categories
Not Available
UNII
467LU0UCUW
CAS number
351862-32-3
Weight
Average: 348.421
Monoisotopic: 348.163791467
Chemical Formula
C22H21FN2O
InChI Key
HKFMQJUJWSFOLY-OAQYLSRUSA-N
InChI
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
IUPAC Name
{[(2R)-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}({[5-(4-fluorophenyl)pyridin-3-yl]methyl})amine
SMILES
FC1=CC=C(C=C1)C1=CN=CC(CNC[C@H]2CCC3=CC=CC=C3O2)=C1

Pharmacology

Indication

Investigated for use/treatment in schizophrenia and schizoaffective disorders and parkinson's disease.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 1ANot AvailableHuman
UD(2) dopamine receptor
partial agonist
Human
UD(3) dopamine receptor
ligand
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
5293585
BindingDB
50027256
ChEMBL
CHEMBL220808
Wikipedia
Sarizotan

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3RecruitingTreatmentRett's Syndrome1
3CompletedTreatmentDyskinesias / Parkinson's Disease (PD)1
Not AvailableTerminatedTreatmentNeuroleptic-Induced Tardive Dyskinesia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000894 mg/mLALOGPS
logP3.41ALOGPS
logP4.29ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area34.15 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.63 m3·mol-1ChemAxon
Polarizability38.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Phenylpyridines
Direct Parent
Phenylpyridines
Alternative Parents
1-benzopyrans / Fluorobenzenes / Aralkylamines / Alkyl aryl ethers / Aryl fluorides / Heteroaromatic compounds / Oxacyclic compounds / Dialkylamines / Azacyclic compounds / Organofluorides
show 1 more
Substituents
3-phenylpyridine / Chromane / Benzopyran / 1-benzopyran / Alkyl aryl ether / Fluorobenzene / Halobenzene / Aralkylamine / Aryl fluoride / Aryl halide
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Johnston TH, Brotchie JM: Drugs in development for Parkinson's disease. Curr Opin Investig Drugs. 2004 Jul;5(7):720-6. [PubMed:15298067]
  2. Newman-Tancredi A, Assie MB, Leduc N, Ormiere AM, Danty N, Cosi C: Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia. Int J Neuropsychopharmacol. 2005 Sep;8(3):341-56. Epub 2005 Feb 11. [PubMed:15707540]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Bartoszyk GD, Van Amsterdam C, Greiner HE, Rautenberg W, Russ H, Seyfried CA: Sarizotan, a serotonin 5-HT1A receptor agonist and dopamine receptor ligand. 1. Neurochemical profile. J Neural Transm (Vienna). 2004 Feb;111(2):113-26. Epub 2003 Dec 31. [PubMed:14767715]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Ligand
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Bartoszyk GD, Van Amsterdam C, Greiner HE, Rautenberg W, Russ H, Seyfried CA: Sarizotan, a serotonin 5-HT1A receptor agonist and dopamine receptor ligand. 1. Neurochemical profile. J Neural Transm (Vienna). 2004 Feb;111(2):113-26. Epub 2003 Dec 31. [PubMed:14767715]

Drug created on March 19, 2008 10:33 / Updated on August 02, 2018 05:36