| Identification | Back Directory | [Name]
APILIMOD | [CAS]
541550-19-0 | [Synonyms]
Sta5326
Sta-5326
APILIMOD
Sta 5326
APILIMODUM
Apilimod, >98%
ApiliMod(STA5326)
STA 5326; STA5326; STA-5326
3-Methylbenzaldehyde [6-(4-morpholinyl)-2-[2-(2-pyridinyl)ethoxy]-4-pyrimidinyl]hydrazone
3-Methylbenzaldehyde 2-[6-(4-Morpholinyl)-2-[2-(2-pyridinyl)ethoxy]-4-
pyriMidinyl]hydrazone
Benzaldehyde,3-methyl-,2-[6-(4-morpholinyl)-2-[2-(2-pyridinyl)ethoxy]-4-pyrimidinyl]hydrazone
4-{6-[(2E)-2-(3-Methylbenzylidene)hydrazino]-2-[2-(2-pyridinyl)ethoxy]-4-pyrimidinyl}morpholine
(E)-4-(6-(2-(3-methylbenzylidene)hydrazinyl)-2-(2-(pyridin-2-yl)ethoxy)pyrimidin-4-yl)morpholine
N-[(e)-(3-methylphenyl)methylideneamino]-6-morpholin-4-yl-2-(2-pyridin-2-ylethoxy)pyrimidin-4-amine
4-{6-[(E)-2-[(3-methylphenyl)methylidene]hydrazin-1-yl]-2-[2-(pyridin-2-yl)ethoxy]pyrimidin-4-yl}morpholine | [Molecular Formula]
C23H26N6O2 | [MDL Number]
MFCD09954108 | [MOL File]
541550-19-0.mol | [Molecular Weight]
418.49 |
| Chemical Properties | Back Directory | [Boiling point ]
655.1±65.0 °C(Predicted) | [density ]
1.24 | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO (>25 mg/ml) | [form ]
solid | [pka]
12.56±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [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]
Wada et al. (2007), Selective abrogation of Th1 response by STA-5326, a potent IL-12/IL23 inhibitor; Blood 109 1156
Cai et al. (2013), PIKfyve, a class III PI-kinase, is the target of the small molecule IL12/23 inhibitor apilimod and a new player in toll-like receptor signaling; Chem. Biol., 20 912
Gayle et al. (2016), Identification of apilimod as a first-in-class PIKfyve kinase inhibitor for treatment of B-cell non-Hodgkin lymphoma; Blood, 129 1768
Kang et al. (2020), Inhibition of PIKfyve kinase prevents infection by Zaire ebola virus and SARS-CoV-2; Proc. Natl. Acad. Sci. USA 117 20803 |
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