NAXIFYLLINE

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 Search

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

Description
Sources: https://adisinsight.springer.com/drugs/800005653 | https://www.ncbi.nlm.nih.gov/pubmed/11901047 | https://www.ncbi.nlm.nih.gov/pubmed/10636259 | https://www.ncbi.nlm.nih.gov/pubmed/9191953

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
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	11714886

Patents

Sample Use Guides

In Vivo Use Guide

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.

Name

Type

Language

NAXIFYLLINE

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