caffeine   Click here for help

GtoPdb Ligand ID: 407

Synonyms: Peyona®
Approved drug PDB Ligand
caffeine is an approved drug (FDA (no history prior to 1999), EMA (2009))
Comment: Caffeine is a central nervous system stimulant that causes increased alertness and agitation.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 61.82
Molecular weight 194.08
XLogP 1.55
No. Lipinski's rules broken 0
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Canonical SMILES Cn1cnc2c1c(=O)n(C)c(=O)n2C
Isomeric SMILES Cn1cnc2c1c(=O)n(C)c(=O)n2C
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
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Antinociceptive effects of novel A2B adenosine receptor antagonists.
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Characterization of human and rodent native and recombinant adenosine A(2B) receptors by radioligand binding studies.
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1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: development and characterization of adenosine A2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity.
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Functional characterization of the A2b adenosine receptor in NIH 3T3 fibroblasts.
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Caffeine analogs: structure-activity relationships at adenosine receptors.
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6. Deckert J, Berger W, Kleopa K, Heckers S, Ransmayr G, Heinsen H, Beckmann H, Riederer P. (1993)
Adenosine A1 receptors in human hippocampus: inhibition of [3H]8-cyclopentyl-1,3-dipropylxanthine binding by antagonist drugs.
Neurosci Lett, 150 (2): 191-4. [PMID:8469419]
7. Grahner B, Winiwarter S, Lanzner W, Müller CE. (1994)
Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.
J Med Chem, 37 (10): 1526-34. [PMID:8182711]
8. Jacobson KA IJzerman AP, Linden J. (1999)
1,3-Dialkylxanthine derivatives having high potency as antagonists at human A2B adenosine receptors.
Drug Dev Res, (47): 45-53.
9. Kim SA, Marshall MA, Melman N, Kim HS, Müller CE, Linden J, Jacobson KA. (2002)
Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions.
J Med Chem, 45 (11): 2131-8. [PMID:12014951]
10. 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]
11. Müller CE, Maurinsh J, Sauer R. (2000)
Binding of [3H]MSX-2 (3-(3-hydroxypropyl)-7-methyl-8-(m-methoxystyryl)-1-propargylxanthine) to rat striatal membranes--a new, selective antagonist radioligand for A(2A) adenosine receptors.
Eur J Pharm Sci, 10 (4): 259-65. [PMID:10838015]