Rolofylline

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.

Rolofylline

Clinical data
ATC code	C03BD (WHO)
Legal status
Legal status	US: ℞-only
Identifiers
IUPAC name 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
ECHA InfoCard	100.190.068
Chemical and physical data
Formula	C20H28N4O2
Molar mass	356.470 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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

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]