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P7C3

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
P7C3
Identifiers
  • 1-anilino-3-(3,6-dibromocarbazol-9-yl)propan-2-ol
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H18Br2N2O
Molar mass474.196 g·mol−1
3D model (JSmol)
  • c4ccccc4NCC(O)Cn2c1ccc(Br)cc1c(c3)c2ccc3Br
  • InChI=1S/C21H18Br2N2O/c22-14-6-8-20-18(10-14)19-11-15(23)7-9-21(19)25(20)13-17(26)12-24-16-4-2-1-3-5-16/h1-11,17,24,26H,12-13H2 ☒N
  • Key:FZHHRERIIVOATI-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

P7C3 (pool 7, compound 3) is adrug related tolatrepirdine (dimebon) which hasneuroprotective andproneurogenic effects and may be potentially useful for the treatment ofAlzheimer's disease and similarneurodegenerative disorders. Thepharmacological effects of P7C3in vitro resemble those ofendogenousproneurogenicpeptides such asfibroblast growth factor 1 (FGF-1), and the proneurogenic activity of P7C3 was around thirty times that oflatrepirdine when they were compared in mice. P7C3 was chosen for further animal studies on the basis of favorablepharmacokinetic factors, such as its highoralbioavailability and longduration of action, but several other related compounds showed similar activity such as the more potent fluorinated analogueP7C3A20 which is up to ten times stronger again, and the methoxy analogueP7C3-OMe, for which it was determined that the (R)enantiomer is the active form.[1]

P7C3A20 and (R)-P7C3-OMe

Themechanism of action of the P7C3 series of compounds involves activation ofnicotinamide phosphoribosyltransferase (NAMPT), therate-limitingenzyme responsible for thetransformation ofnicotinamide intonicotinamide adenine dinucleotide (NAD).[2] By activating NAMPT, the P7C3 compounds result in an increase inintracellular levels of NAD.[2]

References

[edit]
  1. ^Pieper AA, Xie S, Capota E, Estill SJ, Zhong J, Long JM, Becker GL, Huntington P, Goldman SE, Shen CH, Capota M, Britt JK, Kotti T, Ure K, Brat DJ, Williams NS, MacMillan KS, Naidoo J, Melito L, Hsieh J, De Brabander J, Ready JM, McKnight SL (July 2010)."Discovery of a proneurogenic, neuroprotective chemical".Cell.142 (1):39–51.doi:10.1016/j.cell.2010.06.018.PMC 2930815.PMID 20603013.
  2. ^abWang G, Han T, Nijhawan D, Theodoropoulos P, Naidoo J, Yadavalli S, Mirzaei H, Pieper AA, Ready JM, McKnight SL (2014)."P7C3 neuroprotective chemicals function by activating the rate-limiting enzyme in NAD salvage".Cell.158 (6):1324–34.doi:10.1016/j.cell.2014.07.040.PMC 4163014.PMID 25215490.
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others


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