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R13 (drug)

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
R13
Clinical data
Other names4-Oxo-2-phenyl-4H-chromene-7,8-diyl bis(methylcarbamate)
Routes of
administration
By mouth[1]
Pharmacokinetic data
MetabolitesTropoflavin[1]
Identifiers
  • [8-(Methylcarbamoyloxy)-4-oxo-2-phenylchromen-7-yl]N-methylcarbamate
CAS Number
PubChemCID
UNII
Chemical and physical data
FormulaC19H16N2O6
Molar mass368.345 g·mol−1
3D model (JSmol)
  • CNC(=O)OC1=C(C2=C(C=C1)C(=O)C=C(O2)C3=CC=CC=C3)OC(=O)NC
  • 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 asmall-moleculeflavonoid andorally active,potent, andselectiveagonist of thetropomyosin receptor kinase B (TrkB) – the mainsignaling receptor for theneurotrophinbrain-derived neurotrophic factor (BDNF) – which is under development for the potential treatment ofAlzheimer's disease.[1][2] It is astructural modification andprodrug oftropoflavin (7,8-DHF) with improved potency andpharmacokinetics, namelyoralbioavailability andduration.[1] The compound is a replacement for the earlier tropoflavin prodrugR7 and has similar properties to it.[1][3] It was developed because while R7 displayed a good drug profile in animal studies, it showed almost noconversion into tropoflavin in humanlivermicrosomes.[1] In contrast to R7, R13 is readilyhydrolyzed into tropoflavin in human liver microsomes.[1]

See also

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References

[edit]
  1. ^abcdefgChen C, Wang Z, Zhang Z, Liu X, Kang SS, Zhang Y, Ye K (January 2018)."The prodrug of 7,8-dihydroxyflavone development and therapeutic efficacy for treating Alzheimer's disease".Proc. Natl. Acad. Sci. U.S.A.115 (3):578–583.Bibcode:2018PNAS..115..578C.doi:10.1073/pnas.1718683115.PMC 5777001.PMID 29295929.
  2. ^US application 20150274692, Keqiang Ye, "7,8-Dihydoxyflavone and 7,8-substituted flavone derivatives, compositions, and methods related thereto", published 2015-10-01, assigned to Emory University 
  3. ^Liu C, Chan CB, Ye K (2016)."7,8-dihydroxyflavone, a small molecular TrkB agonist, is useful for treating various BDNF-implicated human disorders".Transl Neurodegener.5 2.doi:10.1186/s40035-015-0048-7.PMC 4702337.PMID 26740873.

External links

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Angiopoietin
CNTF
EGF (ErbB)
EGF
(ErbB1/HER1)
ErbB2/HER2
ErbB3/HER3
ErbB4/HER4
FGF
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LNGF (p75NTR)
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GFRα1
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SCF (c-Kit)
TGFβ
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