Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C26H31Cl2N3.3H3O4P |
| Molecular Weight | 750.436 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O.CCN(CC)CCCC(C)NC1=CC(\C=C\C2=C(Cl)C=CC=C2)=NC3=CC(Cl)=CC=C13
InChI
InChIKey=NHNXMYYNFQHZMQ-XPGLNUPKSA-N
InChI=1S/C26H31Cl2N3.3H3O4P/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;3*1-5(2,3)4/h6-7,10-15,17-19H,4-5,8-9,16H2,1-3H3,(H,29,30);3*(H3,1,2,3,4)/b14-12+;;;
| 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 | ( + / - ) |
| Molecular Formula | H3O4P |
| Molecular Weight | 97.9952 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| [On the problem of the comparative effectiveness of aminoquinol and acriouine therapy in lambliasis]. | 1967 Feb |
|
| Crystallographic and spectroscopic studies of native, aminoquinol, and monovalent cation-bound forms of methylamine dehydrogenase from Methylobacterium extorquens AM1. | 1998 Oct 2 |
|
| Treating small fiber neuropathy by topical application of a small molecule modulator of ligand-induced GFRα/RET receptor signaling. | 2014 Feb 11 |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:41:24 GMT 2023
by
admin
on
Sat Dec 16 09:41:24 GMT 2023
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| Record UNII |
K0588F7XOC
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| Record Status |
Validated (UNII)
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| Record Version |
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6444420
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3653-53-0
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admin on Sat Dec 16 09:41:24 GMT 2023 , Edited by admin on Sat Dec 16 09:41:24 GMT 2023
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |
