IBMX

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IBMX
Skeletal formula of IBMX
Space-filling model of the IBMX model
Names
IUPAC name
1-Methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
Other names
3-Isobutyl-1-methylxanthine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.044.767
KEGG
UNII
Properties
C10H14N4O2
Molar mass 222.3 g/mol
Appearance White solid
Melting point 199 to 201 °C (390 to 394 °F; 472 to 474 K)
Solubility Soluble in ethanol, DMSO, and methanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

IBMX (3-isobutyl-1-methylxanthine), like other methylated xanthine derivatives, is both a:

  1. competitive nonselective phosphodiesterase inhibitor[1] which raises intracellular cAMP, activates PKA, inhibits TNFα[2][3] and leukotriene[4] synthesis, and reduces inflammation and innate immunity,[4] and
  2. nonselective adenosine receptor antagonist.[5]

As a phosphodiesterase inhibitor, IBMX has IC50 = 2–50 μM[6] and does not inhibit PDE8 or PDE9.[7]

References[edit]

  1. ^ Essayan, DM (November 2001). "Cyclic Nucleotide Phosphodiesterases". The Journal of Allergy and Clinical Immunology. 108 (5): 671–80. PMID 11692087. doi:10.1067/mai.2001.119555. 
  2. ^ Deree, J; Martins, JO; Melbostad, H; Loomis, WH; Coimbra, R (June 2008). "Insights into the Regulation of TNF-α Production in Human Mononuclear Cells: The Effects of Non-Specific Phosphodiesterase Inhibition". Clinics (São Paulo, Brazil). 63 (3): 321–8. PMC 2664230Freely accessible. PMID 18568240. doi:10.1590/S1807-59322008000300006. 
  3. ^ Marques, LJ; Zheng, L; Poulakis, N; Guzman, J; Costabel, U (February 1999). "Pentoxifylline Inhibits TNF-α Production from Human Alveolar Macrophages". American Journal of Respiratory and Critical Care Medicine. 159 (2): 508–11. PMID 9927365. doi:10.1164/ajrccm.159.2.9804085. 
  4. ^ a b Peters-Golden, M; Canetti, C; Mancuso, P; Coffey, MJ (15 January 2005). "Leukotrienes: Underappreciated Mediators of Innate Immune Responses" (PDF). Journal of Immunology. 174 (2): 589–94. PMID 15634873. doi:10.4049/jimmunol.174.2.589. 
  5. ^ Daly, JW; Jacobson, KA; Ukena, D (1987). "Adenosine Receptors: Development of Selective Agonists and Antagonists". Progress in Clinical and Biological Research. 230: 41–63. PMID 3588607. 
  6. ^ Beavo, JA; Rogers, NL; Crofford, OB; Hardman, JG; Sutherland, EW; Newman, EV (November 1970). "Effects of Xanthine Derivatives on Lipolysis and on Adenosine 3',5'-Monophosphate Phosphodiesterase Activity". Molecular Pharmacology. 6 (6): 597–603. PMID 4322367. 
  7. ^ Soderling, SH; Beavo, JA (April 2000). "Regulation of cAMP and cGMP Signaling: New Phosphodiesterases and New Functions". Current Opinion in Cell Biology. 12 (2): 174–9. PMID 10712916.