AMINOQUINOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H31Cl2N3
Molecular Weight	456.45
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCCC(C)NC1=CC(\C=C\C2=CC=CC=C2Cl)=NC3=C1C=CC(Cl)=C3

InChI

InChIKey=CMLVHSVFSYNMGM-WYMLVPIESA-N

InChI=1S/C26H31Cl2N3/c1-4-31(5-2)16-8-9-19(3)29-26-18-22(14-12-20-10-6-7-11-24(20)28)30-25-17-21(27)13-15-23(25)26/h6-7,10-15,17-19H,4-5,8-9,16H2,1-3H3,(H,29,30)/b14-12+

HIDE SMILES / InChI

Molecular Formula	C26H31Cl2N3
Molecular Weight	456.45
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12441171 | https://www.ncbi.nlm.nih.gov/pubmed/24449858 | https://www.ncbi.nlm.nih.gov/pubmed/5988391 | https://www.ncbi.nlm.nih.gov/pubmed/5597939

Aminoquinol (XIB4035) is a nonpeptidyl small molecule agonist for GFRalpha-1. XIB4035 concentration-dependently inhibited [(125)I]GDNF binding in Neuro-2A cells with an IC(50) of 10.4 uM. GDNF induced autophosphorylation of Ret protein, and promoted neurite outgrowth in Neuro-2A cells. XIB4035, like GDNF, induced Ret autophosphorylation in the Neuro-2A cells. Moreover, XIB4035 promoted neurite outgrowth in a concentration-dependent manner. These results show that XIB4035 may act as an agonist at GFRalpha-1 receptor complex, and mimic neurotrophic effects of GDNF in Neuro-2A cells. It has been shown that topical application of XIB4035 is an effective treatment for small-fiber neuropathy (SFN). Topical application of GFRα/RET receptor signaling modulators may be a unique therapy for SFN, and XIB4035 is a candidate therapeutic agent. Aminoquinol has been also used in the therapy of cutaneous leishmaniasis and lambliasis.

Approval Year

PubMed

Title	Date	PubMed
[ON THE EFFECTIVENESS OF TREATMENT OF LAMBLIASIS IN CHILDREN WITH AMINOQUINOL].	1965 Apr	14312042
[On the problem of the comparative effectiveness of aminoquinol and acriouine therapy in lambliasis].	1967 Feb	5597939
Crystallographic and spectroscopic studies of native, aminoquinol, and monovalent cation-bound forms of methylamine dehydrogenase from Methylobacterium extorquens AM1.	1998 Oct 2	9748238
Treating small fiber neuropathy by topical application of a small molecule modulator of ligand-induced GFRα/RET receptor signaling.	2014 Feb 11	24449858

Patents

Sample Use Guides

In Vivo Use Guide

A cream containing XIB4035 (1.2 mM) was generated and applied directly to the hind paws of GFAP-DN-erbB4 and wild type mice twice daily for a period of 4 weeks starting at the time of weaning (P21).

Route of Administration: Topical

In Vitro Use Guide

The binding of [125I]GDNF to the Neuro-2A cells was concentration-dependently inhibited by Aminoquinol (XIB4035). IC50 value of XIB4035 in displacing [125I]GDNF binding was 10.4 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:23:46 GMT 2023` Edited by `admin` on `Fri Dec 15 16:23:46 GMT 2023`
Record UNII	CH1Y88E2AY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AMINOQUINOL

Official Name

English

1,4-PENTANEDIAMINE, N4-(7-CHLORO-2-((1E)-2-(2-CHLOROPHENYL)ETHENYL)-4-QUINOLINYL)-N1,N1-DIETHYL-

Systematic Name

English

XIB4035

Code

English

XIB-4035

Code

English

aminoquinol [INN]

Common Name

English

7-CHLORO-2-(O-CHLOROSTYRYL)-4-((4-(DIETHYLAMINO)-1-METHYLBUTYL)AMINO)QUINOLINE

Common Name

English

GNF-PF-2659

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C277