SCH-442,416

SCH-442,416
Names
Preferred IUPAC name
2-(Furan-2-yl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine
Other names
SCH-442,416
Identifiers
CAS Number
  • 316173-57-6 ☒N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL136689 checkY
ChemSpider
  • 8843413 checkY
IUPHAR/BPS
  • 3283
PubChem CID
  • 10668061
UNII
  • ZMC4G1W59S ☒N
CompTox Dashboard (EPA)
  • DTXSID70443263 Edit this at Wikidata
InChI
  • InChI=1S/C20H19N7O2/c1-28-14-8-6-13(7-9-14)4-2-10-26-18-15(12-22-26)19-23-17(16-5-3-11-29-16)25-27(19)20(21)24-18/h3,5-9,11-12H,2,4,10H2,1H3,(H2,21,24) checkY
    Key: AEULVFLPCJOBCE-UHFFFAOYSA-N checkY
  • InChI=1/C20H19N7O2/c1-28-14-8-6-13(7-9-14)4-2-10-26-18-15(12-22-26)19-23-17(16-5-3-11-29-16)25-27(19)20(21)24-18/h3,5-9,11-12H,2,4,10H2,1H3,(H2,21,24)
    Key: AEULVFLPCJOBCE-UHFFFAOYAA
  • n1n3c(nc4c(c3nc1c2occc2)cnn4CCCc5ccc(OC)cc5)N
Properties
Chemical formula
 C20H19N7O2
Molar mass 389.410
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

SCH-442,416 is a highly selective adenosine A2a subtype receptor antagonist. It is widely used in its 11C radiolabelled form to map the distribution of A2a receptors in the brain, where they are mainly found in the striatum, nucleus accumbens, and olfactory tubercle.[1] Given its distribution in the brain, A2a receptors have been investigated for the treatment of various neurological disorders, and SCH-442,416 has shown promise in treatment of depression,[2] Parkinson's disease,[3] and catalepsy.[4]

References

  1. ^ Moresco RM, Todde S, Belloli S, Simonelli P, Panzacchi A, Rigamonti M, et al. (April 2005). "In vivo imaging of adenosine A2A receptors in rat and primate brain using [11C]SCH442416". European Journal of Nuclear Medicine and Molecular Imaging. 32 (4): 405–13. doi:10.1007/s00259-004-1688-5. PMID 15549298. S2CID 20909406.
  2. ^ El Yacoubi M, Costentin J, Vaugeois JM (December 2003). "Adenosine A2A receptors and depression". Neurology. 61 (11 Suppl 6): S82-7. doi:10.1212/01.wnl.0000095220.87550.f6. PMID 14663017. S2CID 36219448.
  3. ^ Matsuya T, Takuma K, Sato K, Asai M, Murakami Y, Miyoshi S, et al. (March 2007). "Synergistic effects of adenosine A2A antagonist and L-DOPA on rotational behaviors in 6-hydroxydopamine-induced hemi-Parkinsonian mouse model". Journal of Pharmacological Sciences. 103 (3): 329–32. doi:10.1254/jphs.scz070058. PMID 17341841.
  4. ^ Mihara T, Noda A, Arai H, Mihara K, Iwashita A, Murakami Y, et al. (July 2008). "Brain adenosine A2A receptor occupancy by a novel A1/A2A receptor antagonist, ASP5854, in rhesus monkeys: relationship to anticataleptic effect". Journal of Nuclear Medicine. 49 (7): 1183–8. doi:10.2967/jnumed.108.051474. PMID 18552135.

External links

  • Molecular Imaging and Contrast Agent Database: SCH-442,416
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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
See also: Receptor/signaling modulators
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