NIRAVOLINE

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 Search

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

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Description
Sources: https://adisinsight.springer.com/drugs/800003260 | https://www.ncbi.nlm.nih.gov/pubmed/10673065 | https://www.ncbi.nlm.nih.gov/pubmed/10481790 | https://www.ncbi.nlm.nih.gov/pubmed/15989506

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

Title	Date	PubMed
Niravoline, a selective kappa-opioid receptor agonist effectively reduces elevated intracranial pressure.	2000-02	10706433
Usefulness of niravoline, an arginine vasopressin inhibitor, on tumour-origin brain oedema.	2000	11450035
Novel developments with selective, non-peptidic kappa-opioid receptor agonists.	1997-10	15989506
Renal and haemodynamic responses to a novel kappa opioid receptor agonist, niravoline (RU 51,599), in rats with cirrhosis.	1996-09	8889966

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)

Name

Type

Language

RU-51599

Preferred Name

English

NIRAVOLINE

Official Name

English

RU51599

Code

English

N-METHYL-2-(M-NITROPHENYL)-N-((1S,2S)-2-(1-PYRROLIDINYL)-1-INDANYL)ACETAMIDE

Systematic Name

English

niravoline [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413