IBMX

Last updated
IBMX
IBMX structure.svg
IBMX 3D spacefill.png
Names
IUPAC name
1-Methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
Other names
3-Isobutyl-1-methylxanthine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.044.767 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12) Yes check.svgY
    Key: APIXJSLKIYYUKG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)
    Key: APIXJSLKIYYUKG-UHFFFAOYAL
  • CC(C)Cn1c2c(c(=O)n(c1=O)C)[nH]cn2
Properties
C10H14N4O2
Molar mass 222.3 g/mol
AppearanceWhite 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

  1. competitive non-selective 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

  1. ↑ Essayan, DM (November 2001). "Cyclic Nucleotide Phosphodiesterases". The Journal of Allergy and Clinical Immunology. 108 (5): 671–80. doi: 10.1067/mai.2001.119555 . PMID   11692087.
  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 (Sao Paulo). 63 (3): 321–8. doi:10.1590/S1807-59322008000300006. PMC   2664230 . PMID   18568240.
  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. doi:10.1164/ajrccm.159.2.9804085. PMID   9927365.
  4. 1 2 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. doi: 10.4049/jimmunol.174.2.589 . PMID   15634873.
  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. doi:10.1016/S0026-895X(25)15265-6. 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. doi:10.1016/s0955-0674(99)00073-3. PMID   10712916.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.