TONAPOFYLLINE

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

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
BG-9928 (Biogen Idec).	2005 Sep	16187697
Potent and orally bioavailable 8-bicyclo[2.2.2]octylxanthines as adenosine A1 receptor antagonists.	2006 Nov 30	17125264
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 Aug 14	17692744
Design and synthesis of novel, potent and selective hypoxanthine analogs as adenosine A(1) receptor antagonists and their biological evaluation.	2017 Mar 15	28238512

Sample Use Guides

In Vivo Use Guide

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

Route of Administration: Oral

Name

Type

Language

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

BG-9928

Code

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