SCH-442,416

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SCH-442,416

IUPAC name 2-(2-furyl)-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
PubChem	10668061
ChemSpider	8843413^Y
ChEMBL	CHEMBL136689^Y
Jmol-3D images	Image 1
SMILES n1n3c(nc4c(c3nc1c2occc2)cnn4CCCc5ccc(OC)cc5)N
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)^Y Key: AEULVFLPCJOBCE-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₂₀H₁₉N₇O₂
Molar mass	389.410
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

SCH-442,416 is a highly selective adenosine A_2a subtype receptor antagonist. It is widely used in its ¹¹C radiolabelled form to map the distribution of A_2a receptors in the brain, where they are mainly found in the striatum, nucleus accumbens, and olfactory tubercle.^[1] Given its distribution in the brain, A_2a 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

↑ Moresco RM, Todde S, Belloli S, Simonelli P, Panzacchi A, Rigamonti M, Galli-Kienle M, Fazio F. In vivo imaging of adenosine A2A receptors in rat and primate brain using [11C]SCH442416. European Journal of Nuclear Medicine and Molecular Imaging. 2005 Apr;32(4):405-13. PMID 15549298
↑ El Yacoubi M, Costentin J, Vaugeois JM. Adenosine A2A receptors and depression. Neurology. 2003 Dec 9;61(11 Suppl 6):S82-7. PMID 14663017
↑ Matsuya T, Takuma K, Sato K, Asai M, Murakami Y, Miyoshi S, Noda A, Nagai T, Mizoguchi H, Nishimura S, Yamada K. Synergistic effects of adenosine A2A antagonist and L-DOPA on rotational behaviors in 6-hydroxydopamine-induced hemi-Parkinsonian mouse model. Journal of Pharmacological Sciences. 2007 Mar;103(3):329-32. PMID 17341841
↑ Mihara T, Noda A, Arai H, Mihara K, Iwashita A, Murakami Y, Matsuya T, Miyoshi S, Nishimura S, Matsuoka N. Brain adenosine A2A receptor occupancy by a novel A1/A2A receptor antagonist, ASP5854, in rhesus monkeys: relationship to anticataleptic effect. Journal of Nuclear Medicine. 2008 Jul;49(7):1183-8. PMID 18552135

External links

Molecular Imaging and Contrast Agent Database: SCH-442,416

Adenosinergics

Receptor
ligands

Agonists	2-(1-Hexynyl)-N-methyladenosine 2-Cl-IB-MECA 2'-MeCCPA 5'-N-ethylcarboxamidoadenosine ATL-146e BAY 60–6583 CCPA CGS-21680 CP-532,903 GR 79236 LUF-5835 LUF-5845 N⁶-Cyclopentyladenosine Regadenoson SDZ WAG 994 UK-432,097

Antagonists	8-Phenyl-1,3-dipropylxanthine Acefylline Aminophylline Bamifylline Caffeine CGS-15943 8-Chlorotheophylline CPX CVT-6883 Dimethazan DPCPX Fenethylline Istradefylline KF-26777 MRE3008F20 MRS-1220 MRS-1334 MRS-1706 MRS-1754 MRS-3777 Paraxanthine Pentoxifylline Preladenant Propentofylline PSB-10 PSB-11 PSB 36 PSB-603 PSB-788 PSB-1115 Rolofylline SCH-442,416 SCH-58261 Theobromine Theophylline VUF-5574 ZM-241,385

Reuptake
inhibitors

Plasmalemmal

ENT inhibitors	Dilazep Dipyridamole Hexobendine Pentoxifylline Propentofylline Barbiturates Ethanol Benzodiazepines

Vesicular

VNT inhibitors

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