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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
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.044.767Edit this at Wikidata
KEGG
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) checkY
    Key: APIXJSLKIYYUKG-UHFFFAOYSA-N checkY
  • 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 mass222.3 g/mol
AppearanceWhite solid
Melting point199 to 201 °C (390 to 394 °F; 472 to 474 K)
SolubilitySoluble in ethanol, DMSO, and methanol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

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

  1. competitive non-selectivephosphodiesterase inhibitor[1] which raises intracellularcAMP, activatesPKA,inhibits TNFα[2][3] andleukotriene[4] synthesis, andreduces inflammation andinnate immunity,[4] and
  2. nonselectiveadenosine receptor antagonist.[5]

As aphosphodiesterase inhibitor, IBMX hasIC50 = 2–50μM[6] and does not inhibitPDE8 orPDE9.[7]

References

[edit]
  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. ^abPeters-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.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.
PDE1
PDE2
PDE3
PDE4
PDE5
PDE7
PDE9
PDE10
PDE11
Non-selective
Unsorted
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others


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