pentoxifylline   Click here for help

GtoPdb Ligand ID: 7095

Synonyms: BL-191 | Trental®
Approved drug PDB Ligand
pentoxifylline is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Pentoxifylline is a methylated xanthine derivative drug which acts as a competitive non-selective phosphodiesterase (PDE) inhibitor [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 78.89
Molecular weight 278.14
XLogP 2.01
No. Lipinski's rules broken 0
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Canonical SMILES CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)C
Isomeric SMILES CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)C
InChI InChI=1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3
1. Essayan DM. (2001)
Cyclic nucleotide phosphodiesterases.
J Allergy Clin Immunol, 108 (5): 671-80. [PMID:11692087]
2. 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]
3. Konrad FM, Neudeck G, Vollmer I, Ngamsri KC, Thiel M, Reutershan J. (2013)
Protective effects of pentoxifylline in pulmonary inflammation are adenosine receptor A2A dependent.
FASEB J, 27 (9): 3524-35. [PMID:23699177]
4. Trevethick MA, Mantell SJ, Stuart EF, Barnard A, Wright KN, Yeadon M. (2008)
Treating lung inflammation with agonists of the adenosine A2A receptor: promises, problems and potential solutions.
Br J Pharmacol, 155 (4): 463-74. [PMID:18846036]
5. Ward A, Clissold SP. (1987)
Pentoxifylline. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic efficacy.
Drugs, 34 (1): 50-97. [PMID:3308412]