Rolofylline

Chemical compound
  • C03BD (WHO)
Legal statusLegal status
  • US: ℞-only
Identifiers
  • 8-(Hexahydro-2,5-methanopentalen-3a(1H)-yl)-3,7-dihydro-1,3-dipropyl-1H-purine-2,6-dione
CAS Number
  • 136199-02-5
PubChem CID
  • 64627
IUPHAR/BPS
  • 5604
DrugBank
  • DB12670
ChemSpider
  • 58188
UNII
  • 7805S5HIHX
KEGG
  • D08989
ChEBI
  • CHEBI:177647
ChEMBL
  • ChEMBL52333
CompTox Dashboard (EPA)
  • DTXSID50929292 Edit this at Wikidata
ECHA InfoCard100.190.068 Edit this at WikidataChemical and physical dataFormulaC20H28N4O2Molar mass356.470 g·mol−13D model (JSmol)
  • Interactive image
  • CCCn1c(=O)c2[nH]c(C34CC5CC(CC(C5)C3)C4)nc2n(CCC)c1=O
InChI
  • InChI=1S/C20H28N4O2/c1-3-5-23-16-15(17(25)24(6-4-2)19(23)26)21-18(22-16)20-10-12-7-13(11-20)9-14(20)8-12/h12-14H,3-11H2,1-2H3,(H,21,22)
  • Key:PJBFVWGQFLYWCB-UHFFFAOYSA-N

Rolofylline (KW-3902) is an experimental diuretic which acts as a selective adenosine A1 receptor antagonist.[1][2] It was discovered at NovaCardia, Inc. which was purchased by Merck & Co., Inc. in 2007.

Development of rolofylline was terminated on September 1, 2009, after the results of a large clinical trial (PROTECT) showed the drug to be no better than placebo for patients with acute heart failure. Participants given rolofylline did show some improvement in shortness of breath, but the drug did not prevent kidney damage or have any significant effect on overall treatment success. Rolofylline was also associated with a higher incidence of seizures and stroke.[3]

References

  1. ^ Givertz MM, Massie BM, Fields TK, Pearson LL, Dittrich HC (October 2007). "The effects of KW-3902, an adenosine A1-receptor antagonist, on diuresis and renal function in patients with acute decompensated heart failure and renal impairment or diuretic resistance". J. Am. Coll. Cardiol. 50 (16): 1551–60. doi:10.1016/j.jacc.2007.07.019. PMID 17936154.
  2. ^ Cotter G, Dittrich HC, Weatherley BD, Bloomfield DM, O'Connor CM, Metra M, Massie BM (October 2008). "The PROTECT pilot study: a randomized, placebo-controlled, dose-finding study of the adenosine A1 receptor antagonist rolofylline in patients with acute heart failure and renal impairment". Journal of Cardiac Failure. 14 (8): 631–40. doi:10.1016/j.cardfail.2008.08.010. PMID 18926433.
  3. ^ Hughes, Sue (September 1, 2009). "Rolofylline fails to PROTECT in acute heart failure". Medscape. Retrieved 2009-09-02.
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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
See also: Receptor/signaling modulators


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