SCH 58261   Click here for help

GtoPdb Ligand ID: 403

Synonyms: SCH-58261 | SCH58261
Compound class: Synthetic organic
Comment: SCH 58261 is a selective adenosine A2A receptor antagonist used as a research tool compound [9]. Reports of its effect in models of Parkinson's disease have been published [2,7].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

SCH 58261 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 100.06
Molecular weight 345.13
XLogP 3.08
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Nc1nc2n(CCc3ccccc3)ncc2c2n1nc(n2)c1ccco1
Isomeric SMILES Nc1nc2n(CCc3ccccc3)ncc2c2n1nc(n2)c1ccco1
InChI 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)
InChI Key UTLPKQYUXOEJIL-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Beukers MW, den Dulk H, van Tilburg EW, Brouwer J, Ijzerman AP. (2000)
Why are A(2B) receptors low-affinity adenosine receptors? Mutation of Asn273 to Tyr increases affinity of human A(2B) receptor for 2-(1-Hexynyl)adenosine.
Mol Pharmacol, 58 (6): 1349-56. [PMID:11093773]
2. Chen JF, Xu K, Petzer JP, Staal R, Xu YH, Beilstein M, Sonsalla PK, Castagnoli K, Castagnoli Jr N, Schwarzschild MA. (2001)
Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease.
J Neurosci, 21 (10): RC143. [PMID:11319241]
3. Dionisotti S, Ongini E, Zocchi C, Kull B, Arslan G, Fredholm BB. (1997)
Characterization of human A2A adenosine receptors with the antagonist radioligand [3H]-SCH 58261.
Br J Pharmacol, 121 (3): 353-60. [PMID:9179373]
4. Jacobson KA, Gao ZG. (2006)
Adenosine receptors as therapeutic targets.
Nat Rev Drug Discov, 5 (3): 247-64. [PMID:16518376]
5. Kull B, Arslan G, Nilsson C, Owman C, Lorenzen A, Schwabe U, Fredholm BB. (1999)
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.
Biochem Pharmacol, 57 (1): 65-75. [PMID:9920286]
6. Ongini E, Dionisotti S, Gessi S, Irenius E, Fredholm BB. (1999)
Comparison of CGS 15943, ZM 241385 and SCH 58261 as antagonists at human adenosine receptors.
Naunyn Schmiedebergs Arch Pharmacol, 359 (1): 7-10. [PMID:9933143]
7. Simola N, Fenu S, Baraldi PG, Tabrizi MA, Morelli M. (2006)
Dopamine and adenosine receptor interaction as basis for the treatment of Parkinson's disease.
J Neurol Sci, 248 (1-2): 48-52. [PMID:16780890]
8. Townsend-Nicholson A, Schofield PR. (1994)
A threonine residue in the seventh transmembrane domain of the human A1 adenosine receptor mediates specific agonist binding.
J Biol Chem, 269 (4): 2373-6. [PMID:8300561]
9. Zocchi C, Ongini E, Conti A, Monopoli A, Negretti A, Baraldi PG, Dionisotti S. (1996)
The non-xanthine heterocyclic compound SCH 58261 is a new potent and selective A2a adenosine receptor antagonist.
J Pharmacol Exp Ther, 276 (2): 398-404. [PMID:8632302]