Structure via PubChem · Public domain (PubChem)
repinotan
Sign in to saveAlso known as BAYx3702
Repinotan (BAYx3702), an aminomethylchroman derivative, is a selective 5-HT1A receptor full agonist with high potency and efficacy. It has neuroprotective effects in animal studies, and was trialed in humans for reducing brain injury following head trauma. It was subsequently trialed up to phase II for treatment of stroke, but while side effects were mild and consisted mainly of nausea, repinotan failed to demonstrate sufficient efficacy to justify further clinical trials. However, repinotan continues to be investigated for other applications, and was found to be effective at counteracting the
Chemical data
- Formula
- C21H24N2O4S
- Molecular weight
- 400.5 g/mol
- IUPAC name
- 2-[4-[[(2R)-3,4-dihydro-2H-chromen-2-yl]methylamino]butyl]-1,1-dioxo-1,2-benzothiazol-3-one
- SMILES
- C1CC2=CC=CC=C2O[C@H]1CNCCCCN3C(=O)C4=CC=CC=C4S3(=O)=O
- InChIKey
- YGYBFMRFXNDIPO-QGZVFWFLSA-N
- XLogP
- 3
- Polar surface area
- 84.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 400.145678
Show 5 more facts
- chemical formula
- C₂₁H₂₄N₂O₄S
- isomeric SMILES
- C1CC2=CC=CC=C2O[C@H]1CNCCCCN3C(=O)C4=CC=CC=C4S3(=O)=O
- canonical SMILES
- C1CC2=CC=CC=C2OC1CNCCCCN3C(=O)C4=CC=CC=C4S3(=O)=O
- Commons category
- Repinotan
- physically interacts with
- 5-hydroxytryptamine receptor 1A
Sources (2)
via Wikidata · CC0
~8 min read
Encyclopedic overview
14 sectionsContents
- Medical uses
- Acute ischemic stroke
- Respiratory depression
- Additional uses
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Properties
- Synthesis
- History
- See also
- References
Repinotan (BAYx3702), an aminomethylchroman derivative, is a selective 5-HT1A receptor full agonist with high potency and efficacy. It has neuroprotective effects in animal studies, and was trialed in humans for reducing brain injury following head trauma. It was subsequently trialed up to phase II for treatment of stroke, but while side effects were mild and consisted mainly of nausea, repinotan failed to demonstrate sufficient efficacy to justify further clinical trials. However, repinotan continues to be investigated for other applications, and was found to be effective at counteracting the respiratory depression produced by morphine, though with slight reduction in analgesic effects.
== Medical uses ==
Excerpted from Wikipedia’s “repinotan” article, available under the CC BY-SA 4.0 licence.