NAV

Repinotan

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
3D
Similar Structures
Weight
Average: 400.49
Monoisotopic: 400.145678435
Chemical Formula
C21H24N2O4S
Synonyms
  • Repinotan
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Pharmacology

Indication

Investigated for use/treatment in strokes, cerebral ischemia, and depression.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
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AbataceptThe metabolism of Repinotan can be increased when combined with Abatacept.
AbirateroneThe metabolism of Repinotan can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Repinotan can be decreased when combined with Acebutolol.
AcetaminophenThe metabolism of Repinotan can be decreased when combined with Acetaminophen.
AdagrasibThe metabolism of Repinotan can be decreased when combined with Adagrasib.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Repinotan hydrochloride1KBQ63168A144980-77-8IGKYREHZJIHPML-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
ChemSpider
172029
ChEMBL
CHEMBL1614652
ZINC
ZINC000001552489
Wikipedia
Repinotan

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAcute Ischemic Stroke / Stroke1

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 Solubility0.0059 mg/mLALOGPS
logP2.11ALOGPS
logP3.07Chemaxon
logS-4.8ALOGPS
pKa (Strongest Basic)9.63Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area75.71 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity107.66 m3·mol-1Chemaxon
Polarizability42.69 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-0udi-0010900000-9b91d7131b9feef93c97
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0021900000-30e1bede5ba2f1afc2c1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-0009000000-e19fcfc2cbbe79180ecd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-0109000000-f90a575967511828c6f8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052e-1965000000-795a2e799a8c6512b964
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01po-2922000000-c117d327d9d85fb1da0a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-213.538549
predicted
DarkChem Lite v0.1.0
[M-H]-196.68587
predicted
DeepCCS 1.0 (2019)
[M+H]+214.370749
predicted
DarkChem Lite v0.1.0
[M+H]+200.05305
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.308949
predicted
DarkChem Lite v0.1.0
[M+Na]+208.86812
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 5-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
  1. 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

Details1. Cytochrome P450 2D6
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
  1. 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