UK-432,097

UK-432,097
Kekulé skeletal formula of UK-432,097
Names
Systematic IUPAC name
(12R,13R,14S,15S)-26-[(2,2-Diphenylethyl)amino]-N-ethyl-13,14-dihydroxy-3,8-dioxo-4,7,9-triaza-2(9,2)-purina-11(2)-pyridina-10(4,1)-piperidina-1(2)-oxolanaundecaphane-15-carboxamide
Identifiers
CAS Number
  • 380221-63-6 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
Abbreviations UK-432,097
ChEMBL
  • ChEMBL1096896
ChemSpider
  • 8009243 ☒N
PubChem CID
  • 9833519
UNII
  • 8L3OAJ1R5A checkY
CompTox Dashboard (EPA)
  • DTXSID70431408 Edit this at Wikidata
InChI
  • InChI=1S/C40H47N11O6/c1-2-41-37(54)33-31(52)32(53)39(57-33)51-24-46-30-34(45-23-28(25-11-5-3-6-12-25)26-13-7-4-8-14-26)48-35(49-36(30)51)38(55)43-19-20-44-40(56)47-27-16-21-50(22-17-27)29-15-9-10-18-42-29/h3-15,18,24,27-28,31-33,39,52-53H,2,16-17,19-23H2,1H3,(H,41,54)(H,43,55)(H2,44,47,56)(H,45,48,49)/t31-,32+,33-,39+/m0/s1 ☒N
    Key: ZOTHAEBAWXWVID-HXEFRTELSA-N ☒N
  • O=C(NCC)[C@H]([C@@H](O)[C@H]1O)O[C@H]1N2C=NC3=C(NCC(C4=CC=CC=C4)C5=CC=CC=C5)N=C(C(NCCNC(NC6CCN(C7=NC=CC=C7)CC6)=O)=O)N=C32
  • O=C(NC2CCN(c1ncccc1)CC2)NCCNC(=O)c5nc3c(ncn3[C@@H]4O[C@H](C(=O)NCC)[C@@H](O)[C@H]4O)c(n5)NCC(c6ccccc6)c7ccccc7
Properties
Chemical formula
 C40H47N11O6
Molar mass 777.887 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

UK-432,097 is a drug developed by Pfizer for the treatment of chronic obstructive pulmonary disease, which acts as a potent and selective agonist of the adenosine A2A receptor.[1] It was discontinued from clinical trials following poor efficacy results,[2] but its high selectivity has made it useful for detailed mapping of the internal structure of the A2A receptor.[3]

References

  1. ^ Russo, Cristina; Arcidiacono, Giuseppe; Polosa, Riccardo (2006). "Adenosine receptors: promising targets for the development of novel therapeutics and diagnostics for asthma". Fundamental and Clinical Pharmacology. 20 (1): 9–19. doi:10.1111/j.1472-8206.2005.00388.x. PMID 16448391. S2CID 20463970.
  2. ^ Safety And Efficacy Of UK-432,097 In Chronic Obstructive Pulmonary Disease. ClinicalTrials.gov
  3. ^ Xu F, Wu H, Katritch V, Han GW, Jacobson KA, Gao ZG, Cherezov V, Stevens RC (March 2011). "Structure of an Agonist-Bound Human A2A Adenosine Receptor". Science. 332 (6027): 322–7. Bibcode:2011Sci...332..322X. doi:10.1126/science.1202793. PMC 3086811. PMID 21393508.
  • v
  • t
  • e
Purine receptor modulators
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
  • Agonists: 2-(1-Hexynyl)-N-methyladenosine
  • 2-Cl-IB-MECA
  • 2'-MeCCPA
  • 4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
  • 5'-N-ethylcarboxamidoadenosine
  • Adenosine
  • ADP
  • AMP
  • Apadenoson
  • ATL-146e
  • ATP
  • BAY 60–6583
  • Binodenoson
  • Capadenoson
  • CCPA
  • CGS-21680
  • CP-532,903
  • Evodenoson
  • GR 79236
  • LUF-5835
  • LUF-5845
  • N6-Cyclopentyladenosine
  • Namodenoson
  • Neladenoson dalanate
  • Piclidenoson
  • Regadenoson
  • SDZ WAG 994
  • Selodenoson
  • Sonedenoson
  • Tecadenoson
  • UK-432,097
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
See also: Receptor/signaling modulators


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