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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
20 mg single, oral
Highest studied dose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources: Page: p.589
unhealthy, ADULT
n = 10
Health Status: unhealthy
Condition: coronary artery disease
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 10
Sources: Page: p.589
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
A1 adenosine receptor agonists and their potential therapeutic applications.
2008 Dec
Selective attenuation of norepinephrine release and stress-induced heart rate increase by partial adenosine A1 agonism.
2011 Mar 28
Chronic therapy with a partial adenosine A1-receptor agonist improves left ventricular function and remodeling in dogs with advanced heart failure.
2013 May
Patents

Patents

Sample Use Guides

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 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
Created
by admin
on Fri Dec 15 17:15:42 GMT 2023
Edited
by admin
on Fri Dec 15 17:15:42 GMT 2023
Record UNII
O519NVW73R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAPADENOSON
INN   WHO-DD  
INN  
Official Name English
BAY-68-4986
Code English
2-AMINO-6-(((2-(4-CHLOROPHENYL)-1,3-THIAZOL-4-YL)METHYL)SULFANYL)-4-(4-(2-HYDROXYETHOXY)PHENYL)PYRIDINE-3,5-DICARBONITRILE
Systematic Name English
capadenoson [INN]
Common Name English
BAY 68-4986
Code English
Capadenoson [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
Code System Code Type Description
SMS_ID
100000127411
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
NCI_THESAURUS
C87279
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
PUBCHEM
9936489
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
INN
8723
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL3235279
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
FDA UNII
O519NVW73R
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
EVMPD
SUB33447
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
CAS
544417-40-5
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID50969597
Created by admin on Fri Dec 15 17:15:42 GMT 2023 , Edited by admin on Fri Dec 15 17:15:42 GMT 2023
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
Related Record Type Details
ACTIVE MOIETY