This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Repinotan
- DrugBank Accession Number
- DB06506
- Background
Repinotan is a high-affinity, selective, full agonist of the 5HT1A-receptor subtype with neuroprotective properties.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Repinotan (DB06506)
- Weight
- Average: 400.49
Monoisotopic: 400.145678435 - Chemical Formula
- C21H24N2O4S
- Synonyms
- Repinotan
Pharmacology
- Indication
Investigated for use/treatment in strokes, cerebral ischemia, and depression.
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Not Available
- Mechanism of action
Repinotan is a 5-HT1A receptor agonist which inhibits glutamate induced depolarization. The effect of repinotan in neuronal cells has been reported to be mediated by a variety of mechanisms/signaling pathways, including activation of the anti-apoptotic phosphatidylinositol 3-kinase (PI-3K) pathway, inhibition of glutamate release (probably via opening of K+ channels leading to membrane hyperpolarization), extracellular-regulated kinase (Erk)-stimulated Bcl-2 expression or inhibition of caspase-3 activity, and increased release of the neurite extension factor S-100 beta.
Target Actions Organism 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Repinotan can be increased when combined with Abatacept. Abiraterone The metabolism of Repinotan can be decreased when combined with Abiraterone. Acebutolol The metabolism of Repinotan can be decreased when combined with Acebutolol. Acetaminophen The metabolism of Repinotan can be decreased when combined with Acetaminophen. Adalimumab The metabolism of Repinotan can be increased when combined with Adalimumab. Almotriptan The metabolism of Repinotan can be decreased when combined with Almotriptan. Alogliptin The metabolism of Repinotan can be decreased when combined with Alogliptin. Aminophenazone The metabolism of Repinotan can be decreased when combined with Aminophenazone. Amiodarone The metabolism of Repinotan can be decreased when combined with Amiodarone. Amitriptyline The metabolism of Amitriptyline can be decreased when combined with Repinotan. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Repinotan hydrochloride 1KBQ63168A 144980-77-8 IGKYREHZJIHPML-UNTBIKODSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrans
- Sub Class
- 1-benzopyrans
- Direct Parent
- 1-benzopyrans
- Alternative Parents
- Benzothiazoles / Aralkylamines / Alkyl aryl ethers / Benzenoids / Organosulfonic acids and derivatives / Amino acids and derivatives / Oxacyclic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds show 2 more
- Substituents
- 1,2-benzothiazole / 1-benzopyran / Alkyl aryl ether / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid derivative show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 05PB82Z52L
- CAS number
- 144980-29-0
- InChI Key
- YGYBFMRFXNDIPO-QGZVFWFLSA-N
- InChI
- InChI=1S/C21H24N2O4S/c24-21-18-8-2-4-10-20(18)28(25,26)23(21)14-6-5-13-22-15-17-12-11-16-7-1-3-9-19(16)27-17/h1-4,7-10,17,22H,5-6,11-15H2/t17-/m1/s1
- IUPAC Name
- 2-[4-({[(2R)-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}amino)butyl]-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione
- SMILES
- O=C1N(CCCCNC[C@H]2CCC3=CC=CC=C3O2)S(=O)(=O)C2=CC=CC=C12
References
- General References
- Not Available
- External Links
- ChemSpider
- 172029
- ChEMBL
- CHEMBL1614652
- ZINC
- ZINC000001552489
- Wikipedia
- Repinotan
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Cerebrovascular Accident / Stroke, Acute, Stroke Ischemic 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 0.0059 mg/mL ALOGPS logP 2.11 ALOGPS logP 3.07 ChemAxon logS -4.8 ALOGPS pKa (Strongest Basic) 9.63 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 75.71 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 107.66 m3·mol-1 ChemAxon Polarizability 42.69 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes 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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Tanigawa T, Heinig R, Kuroki Y, Higuchi S: Evaluation of interethnic differences in repinotan pharmacokinetics by using population approach. Drug Metab Pharmacokinet. 2006 Feb;21(1):61-9. [Article]
Drug created at March 19, 2008 16:35 / Updated at February 21, 2021 18:52