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

Identification

Generic Name
Sarizotan
DrugBank Accession Number
DB06454
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 348.421
Monoisotopic: 348.163791467
Chemical Formula
C22H21FN2O
Synonyms
  • Sarizotan
External IDs
  • EMD-77697

Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDopamine D2 receptor
partial agonist
Humans
UDopamine D3 receptor
ligand
Humans
U5-hydroxytryptamine receptor 1ANot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sarizotan hydrochloride5P71E6YO9H195068-07-6QDLVYMYXOLGZOD-ZMBIFBSDSA-N

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
1-benzopyran / 3-phenylpyridine / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
467LU0UCUW
CAS number
351862-32-3
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

References

General References
Not Available
ChemSpider
5293585
BindingDB
50027256
ChEMBL
CHEMBL220808
ZINC
ZINC000000021067
Wikipedia
Sarizotan

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDyskinesia / Parkinson's Disease (PD)2
2CompletedTreatmentDyskinesia / Parkinson's Disease (PD)1
2CompletedTreatmentParkinson's Disease (PD)1
2, 3TerminatedTreatmentRett Syndrome1
Not AvailableTerminatedTreatmentTardive Dyskinesia caused by neuroleptic drugs1

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

Targets

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Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at March 19, 2008 16:33 / Updated at February 21, 2021 18:52