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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H25N3O3
Molecular Weight 379.4522
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIRAVOLINE

SMILES

CN([C@@H]1[C@H](CC2=C1C=CC=C2)N3CCCC3)C(=O)CC4=CC(=CC=C4)[N+]([O-])=O

InChI

InChIKey=ZSDAQBWGAOKTSI-UNMCSNQZSA-N
InChI=1S/C22H25N3O3/c1-23(21(26)14-16-7-6-9-18(13-16)25(27)28)22-19-10-3-2-8-17(19)15-20(22)24-11-4-5-12-24/h2-3,6-10,13,20,22H,4-5,11-12,14-15H2,1H3/t20-,22-/m0/s1

HIDE SMILES / InChI

Description

Niravoline [RU 49679, RU 51599, niravolin], a novel aqueous diuretic with κ-opioid agonistic action. The drug was originally being developed by Hoechst Marion Roussel. Niravoline is a selective agonist of kappa-opioid receptors having potent aquaretic activity. Niravoline was studied with respect to the treatment of brain oedema, heart failure and liver cirrhosis. Niravoline, administered at moderate doses, safely induced a powerful aquaretic effect in patients with cirrhosis and ascites. Moderate doses of niravoline appeared to be a promising pharmacological tool in the treatment of water retention in patients with cirrhosis. The development of niravoline as an aquaretic for the treatment of cirrhosis with ascites and other hyponatraemic disorders has also been halted.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Biochemical tests and hemodynamic values were determined before and 1, 2, 3 and 24 h after niravoline administration at doses ranging from 0.5 to 2 mg iv in 18 patients with cirrhosis. The highest doses (1.5 mg or 2 mg) induced personality disorders and mild confusion within 2 h.
Route of Administration: Intravenous
In Vitro Use Guide
Rat explants kept in isoosmotic conditions did not exhibit a significant change in AVP secretion regardless of whether Niravoline [RU] was added to the hypothalamic compartment (0.01 - 1 uM, 180 %/explant/h) or to the posterior pituitary compartment (0.01 - 1 uM, 144 %/explant/h)