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8-Phenyltheophylline

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
8-Phenyltheophylline
Skeletal formula of 8-phenyltheophylline
Ball-and-stick model of the 8-phenyltheophylline molecule
Clinical data
ATC code
  • None
Identifiers
  • 8-Phenyl-1,3-dimethyl-7H-purine-2,6-dione
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H12N4O2
Molar mass256.265 g·mol−1
3D model (JSmol)
  • Cn3c(=O)c2nc(c1ccccc1)[nH]c2n(C)c3=O
  • InChI=1S/C13H12N4O2/c1-16-11-9(12(18)17(2)13(16)19)14-10(15-11)8-6-4-3-5-7-8/h3-7H,1-2H3,(H,14,15) checkY
  • Key:PJFMAVHETLRJHJ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

8-Phenyltheophylline (8-phenyl-1,3-dimethylxanthine,8-PT) is adrug derived from thexanthine family which acts as apotent andselectiveantagonist for theadenosine receptorsA1 andA2A, but unlike other xanthine derivatives has virtually no activity as aphosphodiesterase inhibitor.[1][2][3] It hasstimulant effects in animals with similar potency tocaffeine.[4] Coincidentally 8-phenyltheophylline has also been found to be a potent and selective inhibitor of the liver enzymeCYP1A2 which makes it likely to cause interactions with other drugs which are normally metabolised by CYP1A2.[5]

See also

[edit]

References

[edit]
  1. ^Scotini E, Carpenedo F, Fassina G (February 1983). "New derivatives of methyl-xanthines: effect of thiocaffeine thiotheophylline and 8-phenyltheophylline on lipolysis and on phosphodiesterase activities".Pharmacological Research Communications.15 (2):131–43.doi:10.1016/s0031-6989(83)80055-1.PMID 6844374.
  2. ^Rabe KF, Magnussen H, Dent G (April 1995). "Theophylline and selective PDE inhibitors as bronchodilators and smooth muscle relaxants".The European Respiratory Journal.8 (4):637–42.doi:10.1183/09031936.95.08040637.PMID 7664866.
  3. ^Howell LL, Morse WH, Spealman RD (September 1990). "Respiratory effects of xanthines and adenosine analogs in rhesus monkeys".The Journal of Pharmacology and Experimental Therapeutics.254 (3):786–91.PMID 2395111.
  4. ^Spealman RD (1988). "Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism".Psychopharmacology.95 (1):19–24.doi:10.1007/bf00212759.PMID 3133696.S2CID 11539292.
  5. ^Murray S, Odupitan AO, Murray BP, Boobis AR, Edwards RJ (March 2001). "Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline".Xenobiotica; the Fate of Foreign Compounds in Biological Systems.31 (3):135–51.doi:10.1080/00498250110043292.PMID 11465391.S2CID 23506958.
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
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