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Rolofylline

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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

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 incidenceofseizures and stroke.^[3]

References[edit]

^ 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.

^ 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.

^ Hughes, Sue (September 1, 2009). "Rolofylline fails to PROTECT in acute heart failure". Medscape. Retrieved 2009-09-02.