Sarizotan
Star0
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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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDopamine D2 receptor partial agonistHumans UDopamine D3 receptor ligandHumans U5-hydroxytryptamine receptor 1A Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
Ingredient UNII CAS InChI Key Sarizotan hydrochloride 5P71E6YO9H 195068-07-6 QDLVYMYXOLGZOD-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
- External Links
- ChemSpider
- 5293585
- BindingDB
- 50027256
- ChEMBL
- CHEMBL220808
- ZINC
- ZINC000000021067
- Wikipedia
- Sarizotan
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Dyskinesia / Parkinson's Disease (PD) 2 2 Completed Treatment Dyskinesia / Parkinson's Disease (PD) 1 2 Completed Treatment Parkinson's Disease (PD) 1 2, 3 Terminated Treatment Rett Syndrome 1 Not Available Terminated Treatment Tardive Dyskinesia caused by neuroleptic drugs 1
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
Property Value Source Water Solubility 0.000894 mg/mL ALOGPS logP 3.41 ALOGPS logP 4.29 Chemaxon logS -5.6 ALOGPS pKa (Strongest Basic) 8.86 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 34.15 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 100.63 m3·mol-1 Chemaxon Polarizability 38.19 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-5780d5816c8ba66d0aed Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-002b-0209000000-c7213e268a50a5bd7d82 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-25d648596c8d2ab965fb Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00kb-4229000000-0c36d6de0d610356494f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0911000000-df5d3e4426ec3c066d1c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-1911000000-4a2fd3b9d4090f45fcaf Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 190.80858 predictedDeepCCS 1.0 (2019) [M+H]+ 193.16656 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.23178 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDopamine D2 receptor
- 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
- 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]
2. DetailsDopamine D3 receptor
- 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
- 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]
3. Details5-hydroxytryptamine receptor 1A
- 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
- Johnston TH, Brotchie JM: Drugs in development for Parkinson's disease. Curr Opin Investig Drugs. 2004 Jul;5(7):720-6. [Article]
- 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