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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 of TONAPOFYLLINE

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Potent and orally bioavailable 8-bicyclo[2.2.2]octylxanthines as adenosine A1 receptor antagonists.
2006 Nov 30
Role of adenosine antagonism in the cardiorenal syndrome.
2008 Winter
Protective effect of tonapofylline (BG9928), an adenosine A1 receptor antagonist, against cisplatin-induced acute kidney injury in rats.
2009
A1 adenosine receptor antagonists, agonists, and allosteric enhancers.
2009
Tonapofylline: a selective adenosine-1 receptor antagonist for the treatment of heart failure.
2010 Oct
Design and synthesis of novel, potent and selective hypoxanthine analogs as adenosine A(1) receptor antagonists and their biological evaluation.
2017 Mar 15

Sample Use Guides

3, 15, 75, or 225 mg once daily for 10 days
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:51:17 GMT 2023
Edited
by admin
on Sat Dec 16 15:51:17 GMT 2023
Record UNII
83VNU4U44T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TONAPOFYLLINE
INN   USAN  
USAN   INN  
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
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID30187611
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL414157
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
INN
9152
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
SMS_ID
100000154912
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
PUBCHEM
216466
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
EVMPD
SUB128679
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
USAN
UU-148
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
CAS
340021-17-2
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
FDA UNII
83VNU4U44T
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
DRUG BANK
DB12569
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
NCI_THESAURUS
C96194
Created by admin on Sat Dec 16 15:51:17 GMT 2023 , Edited by admin on Sat Dec 16 15:51:17 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY