APILIMOD
APILIMOD Basic information
- Product Name:
- APILIMOD
- Synonyms:
-
- APILIMOD
- APILIMODUM
- (E)-4-(6-(2-(3-methylbenzylidene)hydrazinyl)-2-(2-(pyridin-2-yl)ethoxy)pyrimidin-4-yl)morpholine
- Sta 5326
- Sta5326
- Sta-5326
- ApiliMod(STA5326)
- 3-Methylbenzaldehyde 2-[6-(4-Morpholinyl)-2-[2-(2-pyridinyl)ethoxy]-4- pyriMidinyl]hydrazone
- CAS:
- 541550-19-0
- MF:
- C23H26N6O2
- MW:
- 418.49
- Product Categories:
-
- Inhibitors
- API
- Amines
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Mol File:
- 541550-19-0.mol
APILIMOD Chemical Properties
- Boiling point:
- 655.1±65.0 °C(Predicted)
- Density
- 1.24
- storage temp.
- -20°C
- solubility
- Soluble in DMSO (>25 mg/ml)
- pka
- 12.56±0.10(Predicted)
- form
- solid
- color
- White
- Stability:
- Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- InChI
- 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)
- InChIKey
- HSKAZIJJKRAJAV-UHFFFAOYSA-N
- SMILES
- C(=NNC1C=C(N2CCOCC2)N=C(OCCC2=NC=CC=C2)N=1)C1=CC=CC(C)=C1
APILIMOD Usage And Synthesis
Description
Apilimod (541550-19-0) is a potent (IC50 = 10 nM IFN-g/LPS-stimulated human PMBC’s; IC50 = 1 nM in IFN-g/SAC-stimulated human PMBC’s) IL-12/IL-23 inhibitor downregulating both at the transcriptional level.? Suppresses Th1 but not Th2 immune response.1? Inhibition was also observed in human monocytes, monocyte-derived dendritic cells, and THP-1 cells.? Apilimod’s mechanism of action is mediation of TLR signaling via inhibition of phosphatidylinositol-3-phosphate 5-kinase (PIKfyve; IC50 = 14 nM).2? It displayed selective cytotoxic activity in B-cell non-Hodgkin lymphoma compared with normal cells.3? Apilimod prevented infection of VSV-ZEBOV and VSV-SARS-CoV-2 (IC50 = 50 nM) as well as SARS-CoV-2 strain 2019-nCoVB/USA-1WA/2020.4
Chemical Properties
Off-White Solid
Uses
Apilimod is a small-molecule that selectively suppresses synthesis of IL-12 and IL-23. Apilimod reduces dendritic cell infiltration in psoriasis.
in vivo
Apilimod (10 mg/kg, p.o.) is effective not only when administered throughout the entire experiment, but also when administration is initiated on day 30 when disease is clearly measurable but not maximal. TA-5326 causes a significant reduction in cell number only in the Th1 model, with an average percentage of inhibition of 51%±8% relative to the vehicle control. Apilimod treatment has no effect in the Th2 setting[1]. Apilimod (5 or 20 mg/kg, p.o.) reduces the level of IL-12 p40 in serum without altering body weight in EAU mice. Oral administration of Apilimod reduces the severity of experimental autoimmune uveoretinitis (EAU) by clinical and histopathological analysis[2].
IC 50
IL-4; IL-5; IL-8; IL-12; IL-23
References
[1] YUMIKO WADA. Selective abrogation of Th1 response by STA-5326, a potent IL-12/IL-23 inhibitor.[J]. Blood, 2007, 109 3: 1156-1164. DOI:10.1182/blood-2006-04-019398
[2] XINMING CAI. PIKfyve, a class III PI kinase, is the target of the small molecular IL-12/IL-23 inhibitor apilimod and a player in Toll-like receptor signaling.[J]. Chemistry & biology, 2013, 20 7: 912-921. DOI:10.1016/j.chembiol.2013.05.010
[3] S. GAYLE. Identification of apilimod as a first-in-class PIKfyve kinase inhibitor for treatment of B-cell non-Hodgkin lymphoma.[J]. Blood, 2017, 129 13 1: 1768-1778. DOI:10.1182/blood-2016-09-736892
[4] YUAN-LIN KANG. Inhibition of PIKfyve kinase prevents infection by Zaire ebolavirus and SARS-CoV-2.[J]. bioRxiv : the preprint server for biology, 2020. DOI:10.1101/2020.04.21.053058
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