caffeine

Ligand id: 407

Name: caffeine

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Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 58.44
Molecular weight 194.08
XLogP -0.63
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

References
1. Abo-Salem OM, Hayallah AM, Bilkei-Gorzo A, Filipek B, Zimmer A, Müller CE. (2004)
Antinociceptive effects of novel A2B adenosine receptor antagonists.
J. Pharmacol. Exp. Ther.308 (1): 358-66. [PMID:14563788]
2. Bertarelli DC, Diekmann M, Hayallah AM, Rüsing D, Iqbal J, Preiss B, Verspohl EJ, Müller CE. (2006)
Characterization of human and rodent native and recombinant adenosine A(2B) receptors by radioligand binding studies.
Purinergic Signal.2 (3): 559-71. [PMID:18404493]
3. Borrmann T, Hinz S, Bertarelli DC, Li W, Florin NC, Scheiff AB, Müller CE. (2009)
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.
J. Med. Chem.52 (13): 3994-4006. [PMID:19569717]
4. Brackett LE, Daly JW. (1994)
Functional characterization of the A2b adenosine receptor in NIH 3T3 fibroblasts.
Biochem. Pharmacol.47 (5): 801-14. [PMID:8135856]
5. Daly JW, Hide I, Müller CE, Shamim M. (1991)
Caffeine analogs: structure-activity relationships at adenosine receptors.
Pharmacology42 (6): 309-21. [PMID:1658821]
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 Lett150: 191-194. [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: 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 Sci10 (4): 259-65. [PMID:10838015]