TONAPOFYLLINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H32N4O4
Molecular Weight	416.5139
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN1C2=C(NC(=N2)C34CCC(CCC(O)=O)(CC3)CC4)C(=O)N(CCC)C1=O

InChI

InChIKey=ZWTVVWUOTJRXKM-UHFFFAOYSA-N

InChI=1S/C22H32N4O4/c1-3-13-25-17-16(18(29)26(14-4-2)20(25)30)23-19(24-17)22-10-7-21(8-11-22,9-12-22)6-5-15(27)28/h3-14H2,1-2H3,(H,23,24)(H,27,28)

HIDE SMILES / InChI

Molecular Formula	C22H32N4O4
Molecular Weight	416.5139
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/19828940 | https://www.ncbi.nlm.nih.gov/pubmed/20807184 | https://www.ncbi.nlm.nih.gov/pubmed/16187697 | https://www.ncbi.nlm.nih.gov/pubmed/17692744 | https://adisinsight.springer.com/drugs/800015498

Tonapofylline is a selective oral adenosine A, receptor antagonist, for the potential treatment of congestive heart failure. Oral tonapofylline over the dose range of 3 to 225 mg/day produced significant increases in sodium excretion in patients with stable heart failure without causing kaliuresis or reducing renal function. Tonapofylline may be useful in the clinical setting for the prevention of kidney failure induced by nephrotoxic agents such as cisplatin. Tonapofylline may be renoprotective in the setting of concomitant treatment with a loop-diuretic. Adverse effects were generally mild. Tonapofylline had been in phase III clinical trial for the treatment of acute heart failure. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Design and synthesis of novel, potent and selective hypoxanthine analogs as adenosine A1 receptor antagonists and their biological evaluation.	2017-03-15	28238512
Dual A1/A2B Receptor Blockade Improves Cardiac and Renal Outcomes in a Rat Model of Heart Failure with Preserved Ejection Fraction.	2016-02	26585572
Pharmacokinetics of oral tonapofylline and its acyl-glucuronide metabolite in patients with mild and moderate hepatic impairment.	2012-04	21610206
Pharmacokinetics and pharmacodynamics of tonapofylline in subjects with severe renal impairment and in elderly subjects.	2011-09	21888869
Clinical pharmacokinetics of tonapofylline: evaluation of dose proportionality, oral bioavailability, and gender and food effects in healthy human subjects.	2011-07	20926751
Effects of BG9928, an adenosine A₁ receptor antagonist, in patients with congestive heart failure.	2011-06	20926754
Tonapofylline: a selective adenosine-1 receptor antagonist for the treatment of heart failure.	2010-10	20807184
Protective effect of tonapofylline (BG9928), an adenosine A1 receptor antagonist, against cisplatin-induced acute kidney injury in rats.	2009	19828940
A1 adenosine receptor antagonists, agonists, and allosteric enhancers.	2009	19639278
Role of adenosine antagonism in the cardiorenal syndrome.	2008	19035879
Effects of multiple oral doses of an A1 adenosine antagonist, BG9928, in patients with heart failure: results of a placebo-controlled, dose-escalation study.	2007-08-14	17692744
Potent and orally bioavailable 8-bicyclo[2.2.2]octylxanthines as adenosine A1 receptor antagonists.	2006-11-30	17125264
BG-9928 (Biogen Idec).	2005-09	16187697
Comparison of three different A1 adenosine receptor antagonists on infarct size and multiple cycle ischemic preconditioning in anesthetized dogs.	2004-03	14634049

Sample Use Guides

In Vivo Use Guide

3, 15, 75, or 225 mg once daily for 10 days

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:52:46 GMT 2025` Edited by `admin` on `Wed Apr 02 06:52:46 GMT 2025`
Record UNII	83VNU4U44T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BG-9928

Preferred Name

English

TONAPOFYLLINE

Official Name

English

tonapofylline [INN]

Common Name

English

3-(4-(2,6-DIOXO-1,3-DIPROPYL-2,3,6,7-TETRAHYDRO-1H-PURIN-8-YL)BICYCLO(2.2.2)OCT-1- YL)PROPANOIC ACID

Systematic Name

English

TONAPOFYLLINE [USAN]

Common Name

English

BG9928

Code

English

BICYCLO(2.2.2)OCTANE-1-PROPANOIC ACID, 4-(2,3,6,7-TETRAHYDRO-2,6-DIOXO-1,3-DIPROPYL-1H- PURIN-8-YL)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319