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Details

Stereochemistry ACHIRAL
Molecular Formula C23H26N6O2
Molecular Weight 418.4915
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of APILIMOD

SMILES

CC1=CC(\C=N\NC2=NC(OCCC3=CC=CC=N3)=NC(=C2)N4CCOCC4)=CC=C1

InChI

InChIKey=HSKAZIJJKRAJAV-KOEQRZSOSA-N
InChI=1S/C23H26N6O2/c1-18-5-4-6-19(15-18)17-25-28-21-16-22(29-10-13-30-14-11-29)27-23(26-21)31-12-8-20-7-2-3-9-24-20/h2-7,9,15-17H,8,10-14H2,1H3,(H,26,27,28)/b25-17+

HIDE SMILES / InChI

Description

Apilimod is a small molecule inhibitor of interleukin-12 and interleukin-23 synthesis thereby preventing IL-12/IL-23 mediated immune responses. Apilimod is also observed to inhibit the nuclear accumulation of NF-kappB protein family, and viral infections dependent on phosphatidylinositol-3-phosphate 5-kinase (PIKfyve). Apilimod has been investigated as a potential treatment for a number of autoimmune conditions.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Brief report: a phase IIa, randomized, double-blind, placebo-controlled trial of apilimod mesylate, an interleukin-12/interleukin-23 inhibitor, in patients with rheumatoid arthritis.
2012 Jun
The phosphatidylinositol-3-phosphate 5-kinase inhibitor apilimod blocks filoviral entry and infection.
2017 Apr
Patents

Sample Use Guides

In Vivo Use Guide
In a phase IIa clinical trial for rheumatoid arthritis Apilimod mesylate was administered orally at a dose of 100 mg/day or 100 mg twice per day for up to 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
Apilimod was tested for inhibition of EBOV infection in three cell lines: Vero E6, Huh 7, and hMDM cells. For each cell type, cells were plated in 1 black opaque 96-well plate, for the evaluation of drug cytotoxicity, and 2 clear-bottom, 96-well Operetta plates, for the evaluation of drug efficacy. Apilimod was dissolved in dimethyl sulfoxide (DMSO) and diluted in DMEM with 10% FBS with the final DMSO concentration not exceeding 0.05%. The Apilimod solution was diluted two-fold in an 8-point dilution series and transferred to cell plates 1 h prior to virus infection.
Name Type Language
APILIMOD
INN  
INN  
Official Name English
N-(3-METHYL-BENZYLIDENE)-N'-(6-MORPHOLIN-4-YL-2-(2-PYRIDIN-2-YL-ETHOXY)-PYRIMIDIN-4-YL)-HYDRAZINE
Systematic Name English
APILIMOD [INN]
Common Name English
BENZALDEHYDE, 3-METHYL-, (6-(4-MORPHOLINYL)-2-(2-(2-PYRIDINYL)ETHOXY)-4-PYRIMIDINYL)HYDRAZONE
Common Name English
STA 5326
Code English
BENZALDEHYDE, 3-METHYL-, 2-(6-(4-MORPHOLINYL)-2-(2-(2-PYRIDINYL)ETHOXY)-4-PYRIMIDINYL)HYDRAZONE
Common Name English
STA-5326
Code English
Classification Tree Code System Code
NCI_THESAURUS C129820
Created by admin on Tue Oct 22 05:43:22 UTC 2019 , Edited by admin on Tue Oct 22 05:43:22 UTC 2019
Code System Code Type Description
INN
8763
Created by admin on Tue Oct 22 05:43:22 UTC 2019 , Edited by admin on Tue Oct 22 05:43:22 UTC 2019
PRIMARY
CAS
541550-19-0
Created by admin on Tue Oct 22 05:43:22 UTC 2019 , Edited by admin on Tue Oct 22 05:43:22 UTC 2019
PRIMARY
PUBCHEM
10173277
Created by admin on Tue Oct 22 05:43:22 UTC 2019 , Edited by admin on Tue Oct 22 05:43:22 UTC 2019
PRIMARY
NCI_THESAURUS
C90808
Created by admin on Tue Oct 22 05:43:22 UTC 2019 , Edited by admin on Tue Oct 22 05:43:22 UTC 2019
PRIMARY