CAPADENOSON

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26210506 | https://www.ncbi.nlm.nih.gov/pubmed/28344125 | https://www.ncbi.nlm.nih.gov/pubmed/21185259

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 Target	Pharmacology	Condition	Potency
Adenosine A1 receptor 50 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21185259	Partial Agonist 290		0.1 nM [EC50]
Adenosine A2b receptor 22 Target ID: CHEMBL255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28344125	Agonist 2678		8.94 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stable angina 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22370739 https://www.ncbi.nlm.nih.gov/pubmed/21185259	Primary		Phase II 1132	Unknown Approved Use Unknown
Atrial fibrillation 131 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21185259	Primary		Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
20 mg single, oral Highest studied dose Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22370739 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: https://pubmed.ncbi.nlm.nih.gov/22370739 Page: p.589	Sources: https://pubmed.ncbi.nlm.nih.gov/22370739 Page: p.589

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00DBM0	https://www.1pchem.com/search?query=1P00DBM0
AK Scientific	3517AH	https://aksci.com/item_detail.php?cat=3517AH
Ambeed	A146488	http://www.ambeed.com/search/Search.html?keyword=A146488
ApexBio Technology	A3277	https://www.apexbt.com/catalogsearch/result/?q=A3277
AstaTech	40676	http://astatechinc.com/CPSResult.php?CRNO=40676
BLD Pharm	BD119848	http://www.bldpharm.com/search/Search.html?keyword=BD119848
BOC Sciences	544417-40-5	http://www.bocsci.com/description.asp?cas=544417-40-5
Chem Scene	CS-1228	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1228
Combi-Blocks	QW-1567	http://www.combi-blocks.com/cgi-bin/find.cgi?QW-1567
Debye Scientific	DB-071852	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-071852
Excenen	EX-A848	http://www.excenen.com/searchresultlist.php?id=EX-A848
KeyOrganics	AS-35054	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35054
MedChem Express	HY-14917	https://www.medchemexpress.com/search.html?q=HY-14917&ft=&fa=&fp=
MolPort	MolPort-039-139-587	https://www.molport.com/shop/molecule-link/MolPort-039-139-587
Molnova	M14953	https://www.molnova.com/en/serch-list.html?keywords=M14953
MuseChem	I004000	https://www.musechem.com/product/I004000.html
ShangHai Biochempartner	BCP16060	http://www.biochempartner.com/search_BCP16060
eMolecules	45475559	https://orderbb.emolecules.com/search/#?query=45475559
eNovation Chemicals	D501832	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D501832&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1783873336	https://mcule.com/MCULE-1783873336/

PubMed

Title	Date	PubMed
A1 adenosine receptor agonists and their potential therapeutic applications.	2008 Dec	19012505
Selective attenuation of norepinephrine release and stress-induced heart rate increase by partial adenosine A1 agonism.	2011 Mar 28	21464936
The new oral adenosine A1 receptor agonist capadenoson in male patients with stable angina.	2012 Jul	22370739
Chronic therapy with a partial adenosine A1-receptor agonist improves left ventricular function and remodeling in dogs with advanced heart failure.	2013 May	23564604
Quantification of adenosine A(1) receptor biased agonism: Implications for drug discovery.	2016 Jan 1	26581123
Capadenoson, a clinically trialed partial adenosine A(1) receptor agonist, can stimulate adenosine A(2B) receptor biased agonism.	2017 Jul 1	28344125
Optimization of Thermolytic Response to A(1) Adenosine Receptor Agonists in Rats.	2017 Sep	28652388

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 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

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Name

Type

Language

CAPADENOSON

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