| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H15N7O |
| Molecular Weight | 345.358 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(C=NN2CCC3=CC=CC=C3)C4=NC(=NN14)C5=CC=CO5
InChI
InChIKey=UTLPKQYUXOEJIL-UHFFFAOYSA-N
InChI=1S/C18H15N7O/c19-18-22-16-13(11-20-24(16)9-8-12-5-2-1-3-6-12)17-21-15(23-25(17)18)14-7-4-10-26-14/h1-7,10-11H,8-9H2,(H2,19,22)
| Molecular Formula | C18H15N7O |
| Molecular Weight | 345.358 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
SCH-58261 is an antagonist of the Adenosine A2A receptor with a Kd of 2.3 nM. It was initially identified and developed by Schering-Plough as a potential treatment for neurological conditions such as Parkinson's Disease and Depression. However, the compound suffered from poor solubility and is not active when orally dosed. SCH-58261 became the scaffold for the development of Preladenant (SCH 412348), which did progress to Phase III clinical trials before being discontinued. There has also been an investigation of SCH-58261 as a treatment of hypotension in rat models.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Normotensive rats were dosed with 0.1, 1, 3, and 10 mg/kg of SCH-58261 and monitored for changes in blood pressure (BP) and heart rate (HR). Maximum effect on systolic-BP and diastolic-BP were +19 +/- 3 mmHg and +16 +/- 2 mmHg respectively. Maximal HR increase was + 85 +/- 5 bpm. These effects were recorded 50 minutes after injection and had a half-life of 60 minutes.
Route of Administration:
Intraperitoneal
Chinese Hamster Ovary Cells stably expressing the human A2A adenosine receptor were pre-treated with adenosine deaminase and then incubated for 30 min, 25 degC, pH 7.4 with a [3H]-SCH 58261 concentration ranging from 0.0625 to 64 nM. The specific binding of [3H]-SCH 58261 was rapid, saturable, and increased linearly with respect to protein concentration over the range of 25 ± 250 mg of protein/assay. Binding equilibrium was achieved within 5 min and stable for at least 4 h. A Kd value of 2.3 nM was determined for the A2a adenosine receptors.
