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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24N4O3
Molecular Weight 344.4082
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAXIFYLLINE

SMILES

CCCN1C2=C(NC(=N2)[C@H]3C[C@H]4C[C@@H]3[C@@H]5O[C@H]45)C(=O)N(CCC)C1=O

InChI

InChIKey=OQCJPFYWFGUHIN-GJKBLCTNSA-N
InChI=1S/C18H24N4O3/c1-3-5-21-16-12(17(23)22(6-4-2)18(21)24)19-15(20-16)11-8-9-7-10(11)14-13(9)25-14/h9-11,13-14H,3-8H2,1-2H3,(H,19,20)/t9-,10+,11+,13-,14+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H24N4O3
Molecular Weight 344.4082
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Naxifylline [CVT 124, BG 9719], a small molecule diuretic, is one of a new class of potent and highly selective adenosine A1 receptor antagonists discovered at University of Florida. Naxifylline is an A1 adenosine receptor antagonist used for the treatment of edema associated with congestive heart failure. Naxifylline appears to be one of the more potent and clearly the most A1-selective antagonist reported to date, with K1 values of 0.67 and 0.45 nM, respectively, at the rat and cloned human A1-receptors and with 1800-fold (rat) and 2400-fold (human) subtype selectivity. Naxifylline protects against the decline in renal function observed with diuretic therapy by promoting urine output.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of BG9719 (CVT-124), an A1-adenosine receptor antagonist, and furosemide on glomerular filtration rate and natriuresis in patients with congestive heart failure.
2000 Jan
A(1) receptor blockade induces natriuresis with a favorable renal hemodynamic profile in SHHF/Mcc-fa(cp) rats chronically treated with salt and furosemide.
2001 Dec
Patents

Sample Use Guides

Rats: Thereafter, rats of group 1 received a bolus injection of vehicle (Veh; 0.3 ml of a 3% solution of polyethylene glycol-400 plus 2% ethanol in 0.154 M NaCl solution), followed, at 30-min intervals, by CVT-124 at 0.1, 0.3, 0.5, and 1 mg/kg. Rats of group 2 received intravenous bolus injections of 0.3 ml of the CVT-124 vehicle, following the same course as for group 1. CVT-124 (0.1 to 1 mg/kg) caused dose-dependent increases in urine flow and fractional and absolute sodium excretion of by six- to 10-fold and, at 0.1 mg/kg, increased the GFR.
Route of Administration: Intravenous
In Vitro Use Guide
Naxifylline appears to be one of the more potent and clearly the most A1-selective antagonist reported to date, with K1 values of 0.67 and 0.45 nM, respectively, at the rat and cloned human A1-receptors and with 1800-fold (rat) and 2400-fold (human) subtype selectivity.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:57:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:57:46 GMT 2023
Record UNII
B3G45WC37L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAXIFYLLINE
INN   USAN  
INN   USAN  
Official Name English
CVT-124
Code English
naxifylline [INN]
Common Name English
NAXIFYLLINE [USAN]
Common Name English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-8-(3-OXATRICYCLO(3.2.1.0(SUP 2,4))OCT-6-YL)-1,3-DIPROPYL-, (1S-(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,6.ALPHA.))-
Systematic Name English
BG-9719
Code English
BG9719
Code English
8-[(2S,5,6-exo)-5,6-epoxy-2-norbonyl]-1,3-dipropylxanthine
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C78322
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
Code System Code Type Description
SMS_ID
300000034325
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107805
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
CAS
166374-49-8
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
FDA UNII
B3G45WC37L
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
DRUG BANK
DB06471
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
USAN
LL-32
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
NCI_THESAURUS
C83991
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
INN
8152
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
PUBCHEM
9841075
Created by admin on Fri Dec 15 15:57:46 GMT 2023 , Edited by admin on Fri Dec 15 15:57:46 GMT 2023
PRIMARY
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