Overview
R7 is a small-molecule flavonoid and orally active, potent, and selective agonist of the tropomyosin receptor kinase B (TrkB) – the main signaling receptor for the neurotrophin brain-derived neurotrophic factor (BDNF) – which is under development for the treatment of Alzheimer's disease. It is a structural modification and prodrug of tropoflavin (7,8-DHF) with improved potency and pharmacokinetics, namely oral bioavailability and duration.[1]
Pharmacology
Pharmacokinetics
As R7 is a slightly larger molecule than tropoflavin, 72.5 mg R7 is molecularly equivalent to 50 mg tropoflavin. Relative to a roughly molecularly equivalent dose of tropoflavin, the area-under-curve levels of R7 were found to be 7.2-fold higher upon oral administration to mice, and R7 hence has a greatly improved oral bioavailability in mice of approximately 35%. Moreover, whereas tropoflavin itself is mostly metabolized in mice within 30 minutes, tropoflavin as a metabolite was still detectable in plasma at 8 hours after administration with R7, indicating that R7 sustainably releases tropoflavin into circulation. In accordance, the terminal half-life of R7 is about 195 minutes (3.25 hours) in mice. The Tₘₐₓ of R7 is about 60 minutes in mice, and its Cₘₐₓ for a 78 mg/kg dose was 262 ng/mL, whereas that for a 50 mg/kg dose of tropoflavin was 70 ng/mL.[3] WP
Chemistry
- Formula
- C21H20N2O6 PC
- CAS number
- 1609067-35-7 PC
- Molar mass (g/mol)
- 396.4 PC
- IUPAC name (computed by PubChem)
- [8-
(dimethylcarbamoyloxy) PC- 4- oxo- 2- phenylchromen- 7- yl] N, N- dimethylcarbamate - SMILES
- CN(C)
C(=O) PCOC1=C(C2=C(C=C1) C(=O) C=C(O2) C3=CC=CC=C3) OC(=O) N(C) C - InChIKey
- KHUMQRAGNPGBIE-
UHFFFAOYSA- PCN - PubChem CID
- 73672564
Harm reduction information
No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.
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Sources
- Journal / agency Liu C, Chan CB, Ye K. 7,8-dihydroxyflavone, a small molecular TrkB agonist, is useful for treating various BDNF-implicated human disorders. Translational Neurodegeneration. 2016. doi:10.1186/s40035-015-0048-7 · PMID 26740873 · PMC4702337
- Journal / agency Kazim SF, Iqbal K. Neurotrophic factor small-molecule mimetics mediated neuroregeneration and synaptic repair: emerging therapeutic modality for Alzheimer's disease. Molecular Neurodegeneration. July 2016. doi:10.1186/s13024-016-0119-y · PMID 27400746 · PMC4940708
- Other 7,8-Dihydoxyflavone and 7,8-substituted flavone derivatives, compositions, and methods related thereto
Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.