R13 (drug)

R13

Clinical data
Other names	4-Oxo-2-phenyl-4H-chromene-7,8-diyl bis(methylcarbamate)
Routes of administration	By mouth
Pharmacokinetic data
Metabolites	Tropoflavin
Identifiers
IUPAC name [8-(Methylcarbamoyloxy)-4-oxo-2-phenylchromen-7-yl] N-methylcarbamate
CAS Number	1609067-49-3 Y
PubChem CID	90117609
UNII	OGG19T0LU2
Chemical and physical data
Formula	C19H16N2O6
Molar mass	368.345 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNC(=O)OC1=C(C2=C(C=C1)C(=O)C=C(O2)C3=CC=CC=C3)OC(=O)NC
InChI InChI=1S/C19H16N2O6/c1-20-18(23)26-14-9-8-12-13(22)10-15(11-6-4-3-5-7-11)25-16(12)17(14)27-19(24)21-2/h3-10H,1-2H3,(H,20,23)(H,21,24) Key:NWWRHMSYZTWUBD-UHFFFAOYSA-N

R13 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 potential 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. The compound is a replacement for the earlier tropoflavin prodrug R7 and has similar properties to it. It was developed because while R7 displayed a good drug profile in animal studies, it showed almost no conversion into tropoflavin in human liver microsomes. In contrast to R7, R13 is readily hydrolyzed into tropoflavin in human liver microsomes.

See also

• List of investigational antidepressants
• Tropomyosin receptor kinase B § Agonists

External links

• 7,8-Dihydoxyflavone and 7,8-substituted flavone derivatives, compositions, and methods related thereto (US9975868B2)