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
28822-58-4 YesY
ChEBI CHEBI:34795 YesY
ChEMBL ChEMBL275084 YesY
ChemSpider 3627 YesY
DrugBank DB07954 YesY
IUPHAR ligand 388
Jmol-3D images Image
KEGG C13708 YesY
PubChem 3758
UNII TBT296U68M YesY
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
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 TNF-alpha [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. (2001). "Cyclic nucleotide phosphodiesterases.". J Allergy Clin Immunol. 108 (5): 671–80. doi:10.1067/mai.2001.119555. PMID 11692087. 
  2. ^ Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R. (2008). "Insights into the regulation of TNF-alpha 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-alpha production from human alveolar macrophages". Am. J. Respir. Crit. Care Med. 159 (2): 508–11. doi:10.1164/ajrccm.159.2.9804085. PMID 9927365. 
  4. ^ a b Peters-Golden M, Canetti C, Mancuso P, Coffey MJ. (2005). "Leukotrienes: underappreciated mediators of innate immune responses.". J Immunol. 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.". Prog Clin Biol Res. 230 (1): 41–63. PMID 3588607. 
  6. ^ Mol. Pharmacol 6: 597. 1970.  Missing or empty |title= (help)
  7. ^ Soderling and Beavo Current Opinion in Cell Biol. 2000 12 174