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Details

Stereochemistry ACHIRAL
Molecular Formula C25H18ClN5O2S2
Molecular Weight 520.026
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAPADENOSON

SMILES

NC1=NC(SCC2=CSC(=N2)C3=CC=C(Cl)C=C3)=C(C#N)C(C4=CC=C(OCCO)C=C4)=C1C#N

InChI

InChIKey=CITWCLNVRIKQAF-UHFFFAOYSA-N
InChI=1S/C25H18ClN5O2S2/c26-17-5-1-16(2-6-17)24-30-18(13-34-24)14-35-25-21(12-28)22(20(11-27)23(29)31-25)15-3-7-19(8-4-15)33-10-9-32/h1-8,13,32H,9-10,14H2,(H2,29,31)

HIDE SMILES / InChI

Molecular Formula C25H18ClN5O2S2
Molecular Weight 520.026
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Capadenoson (BAY 68-4986) is a nonnucleoside agonist for the A1 Adenosine Receptor (A1AR) and the A2BAR. Capadenoson has undergone two Phase IIa clinical trials, initially in patients with atrial fibrillation and subsequently in patients with stable angina. Capadenoson has also been shown to decrease cardiac remodeling in an animal model of advanced heart failure and a capadenoson derivative, neladenoson bialanate, recently entered clinical development for the treatment of chronic heart failure. The therapeutic effects of capadenoson are currently thought to be mediated through the A1AR.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.1 nM [EC50]
8.94 null [pEC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Doses

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
In a randomized, double-blind, placebo-controlled, single dose-escalating, multicenter trial the effect of capadenoson at 1, 2.5, 5, 10, and 20 mg was compared versus placebo. Sixty-two male patients with stable angina were enrolled in the study. There was a consistent trend for heart rate reduction at comparable maximum work load in active treatment groups, with significant differences against placebo for 10 and 20 mg.
Route of Administration: Oral
In Vitro Use Guide
In isolated perfused hearts of Wistar and Spontaneously Hypertensive Rats (SHR), norepinephrine release was induced by electrical stimulation under control conditions (S1), and with capadenoson 60 nM (30 µg/l)
Substance Class Chemical
Record UNII
O519NVW73R
Record Status Validated (UNII)
Record Version