Ruxolitinib (INCB018424)

Catalog No.S1378

Ruxolitinib (INCB018424) Chemical Structure

Molecular Weight(MW): 306.37

Ruxolitinib (INCB018424) is the first potent, selective, JAK1/2 inhibitor to enter the clinic with IC50 of 3.3 nM/2.8 nM in cell-free assays, >130-fold selectivity for JAK1/2 versus JAK3.

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Cited by 94 Publications

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Biological Activity

Description Ruxolitinib (INCB018424) is the first potent, selective, JAK1/2 inhibitor to enter the clinic with IC50 of 3.3 nM/2.8 nM in cell-free assays, >130-fold selectivity for JAK1/2 versus JAK3.
Targets
JAK2 [1]
(Cell-free assay)
JAK1 [1]
(Cell-free assay)
2.8 nM 3.3 nM
In vitro

INCB018424 potently and selectively inhibits JAK2V617F-mediated signaling and proliferation in Ba/F3 cells and HEL cells. INCB018424 markedly increases apoptosis in a dose dependent manner in Ba/F3 cells. INCB018424 (64 nM) results in a doubling of cells with depolarized mitochondria in Ba/F3 cells. INCB018424 inhibits proliferating of erythroid progenitors from normal donors and polycythemia vera patients with IC50 of 407 nM and 223 nM, respectively. INCB018424 demonstrates remarkable potency against erythroid colony formation with IC50 of 67nM. [1]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
TF1 NGOzSHlMcW6jc3WgRZN{[Xl? MWSyNEBucW5? NIG3WXdFVVOR NXraSJVOUW6qaXLpeIlwdiCxZjDKRWszKGmwIHj1cYFvKFSIMTDj[YxteyCjc4Pld5Nm\CCjczDpcohq[mm2aX;uJI9nKEWSTz3pcoR2[2WmIGPURXQ2KHCqb4PwbI9zgWyjdHnvckB4cXSqIFnDOVAhd2ZiMD6wNVLPxE1? MWOyNlY6QDB6NB?=
TF1 NVzhfm9FU2mwYYPlJGF{e2G7 NWr5NJFuOjBibXnu MVvEUXNQ M37mbmlvcGmkaYTpc44hd2ZiSlHLNUBqdiCqdX3hckBVTjFiY3XscJMh[XO|ZYPz[YQh[XNiaX7obYJqfGmxbjDv[kBKVDZvaX7keYNm\CCVVFHUN{BxcG:|cHjvdplt[XSrb36ge4l1cCCLQ{WwJI9nKDBwMEK0{txO NFK3eGgzOjZ7OEC4OC=>
Human T cell MYrLbY5ie2ViQYPzZZk> Moe2TY5pcWKrdHnvckBw\iCMQVuzM|EhcW5iaIXtZY4hXCClZXzsd{BmgHC{ZYPzbY5oKEOGMzDhd5Nme3OnZDDhd{BqdmirYnn0bY9vKG:oIFnMNk1{fGmvdXzheIVlKFOWQWS1ZUBxcG:|cHjvdplt[XSrb36ge4l1cCCLQ{WwJI9nKDBwMEKz{txO M{jXWVI{PTRyNkS4
Human monocyte Ml[zT4lv[XOnIFHzd4F6 NGLYe41KdmirYnn0bY9vKG:oIFrBT|IhcW5iaIXtZY4hdW:wb3P5eIV{KGW6cILld5NqdmdiQ1SxOEBie3Onc4Pl[EBieyCrbnjpZol1cW:wIH;mJGdONUOVRj3zeIlufWyjdHXkJHNVSVR3YTDwbI9{eGixconsZZRqd25id3n0bEBKSzVyIH;mJFAvODJ4zszN MlyzNlM2PDB4NEi=
Human monocyte NGC0VZZMcW6jc3WgRZN{[Xl? MV3Jcohq[mm2aX;uJI9nKEqDS{KvNUBqdiCqdX3hckBud26xY4n0[ZMh\XiycnXzd4lv\yCFREG0JIF{e2W|c3XkJIF{KGmwaHnibZRqd25ib3[gTWZP\2GvbXGtd5RqdXWuYYTl[EBUXEGWMTDwbI9{eGixconsZZRqd25id3n0bEBKSzVyIH;mJFAvODNzzszN MUGyN|U1ODZ2OB?=
HEL NE\z[WVEgXSxdH;4bYMhSXO|YYm= NFfYW3Q2KM7:TR?= NGKxU2s1QCCq MYjDfZRwfG:6aXOgbY5l\Xh;MUKuNkU> MYWyOVk{OTN2OR?=
SET-2 NFzFWo9EgXSxdH;4bYMhSXO|YYm= M4jGT|Uh|ryP M3XtWFQ5KGh? MnLvR5l1d3SxeHnjJIlv\GW6PUG4Mlcm M4TaTlI2QTNzM{S5
HT93A NX3xRVdTT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= Ml;GN|IxKG6P NV7JT|lHPSCm NHvrN2dFVVOR MkLhTY5pcWKrdHnvckBw\iCJQ2OtSkBqdmS3Y3XkJIdz[W63bH;jfZRq[yCmaX\m[ZJmdnSrYYTpc44> M1jpNFI2QDB3OU[y
CMK M1rTWWdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NILJWW9KdmirYnn0bY9vKG:oIFPNT{Bk[XK{eXnu[{B1cGViSlHLN2E2PzKYIH31eIF1cW:wIHPlcIwheHKxbHnm[ZJifGmxbh?= M4K3RlI2OzV{MUK0
CMK NIPIephIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MUjJcohq[mm2aX;uJI9nKEOPSzDjZZJzgWmwZzD0bIUhUkGNM1G2N2QhdXW2YYTpc44h[2WubDDwdo9tcW[ncnH0bY9vKHerdHigTWM2OCCxZjCwMlE3OyEQvF2= NX\aNXp2OjV|NUKxNlQ>
CMK MnLES5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NFH6[W9KdmirYnn0bY9vKG:oIFPNT{Bk[XK{eXnu[{B1cGViV2SgTmFMKGOnbHygdJJwdGmoZYLheIlwdiC5aYToJGlEPTBib3[gNE4xPzVizszN NX\ySVNPOjV|NUKxNlQ>
NCI-H460 NVjZ[YhvT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NXXyd5FZTE2VTx?= Mmn6TWM2OD1yLkGzJO69VQ>? MmTBNlUzOTN4N{C=
NCI-H358 NYLW[IZST3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NXXvNVhbTE2VTx?= MmjhTWM2OD1yLkGg{txO MYmyOVIyOzZ5MB?=
A549 Mn;WS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? MW\EUXNQ NHPSTYdKSzVyPUCuNFQh|ryP NXuyRYt1OjV{MUO2O|A>
A549/DDP NFv6fVJIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= M4rxcWROW09? M37NbWlEPTB;MD6yNkDPxE1? MW[yOVIyOzZ5MB?=
NCI-H1299 NUHYToZ7T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M2r6O2ROW09? NX31e5lXUUN3ME2wMlI5KM7:TR?= M1i3OlI2OjF|Nkew
NCI-H2347 MVrHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NYLm[odxTE2VTx?= NGnTNFZKSzVyPUCuNVch|ryP MnqxNlUzOTN4N{C=
A549/DDP Mn3TSpVv[3Srb36gRZN{[Xl? M{O1[lMxKG6P M4XRZ|Q5KGh? M1nZZWROW09? NWK1NIN[TG:5bj3y[Yd2dGG2aX;uJI9nKFOWQWSzJJBpd3OyaH;yfYxifGmxbh?= NV3OSWhSOjV{MUO2O|A>
NCI-H1299 NFL2bWFHfW6ldHnvckBCe3OjeR?= NUT1RnZGOzBibl2= M1XESVQ5KGh? NF3sXnFFVVOR M13nbWRwf25vcnXneYxifGmxbjDv[kBUXEGWMzDwbI9{eGixconsZZRqd25? MnPlNlUzOTN4N{C=
NCI-H2347 M173ZmZ2dmO2aX;uJGF{e2G7 NHHp[mM{OCCwTR?= M{nadVQ5KGh? NFnCb25FVVOR NGfoO3BF\WO{ZXHz[UBqdiCEY3yyJIV5eHKnc4Ppc44> MUGyOVIyOzZ5MB?=
A549/DDP MoniRZBweHSxc3nzJGF{e2G7 MmLBN|Ahdk1? MlO4OFghcA>? MlWwSG1UVw>? M1PJPGlv\HWldHnvckBw\iCjcH;weI9{cXN? NHHJTZkzPTJzM{[3NC=>
NCI-H1299 NX\Cb2ZiSXCxcITvd4l{KEG|c3H5 NFLSb2g{OCCwTR?= MljPOFghcA>? NWXCXmtPTE2VTx?= MlOxTY5lfWO2aX;uJI9nKGGyb4D0c5Nqew>? NYjvUJFKOjV{MUO2O|A>
NCI-H2347 M1GwW2Fxd3C2b4Ppd{BCe3OjeR?= M3fFbFMxKG6P M{XwUlQ5KGh? NXXNV3BmTE2VTx?= M4\vNGlv\HWldHnvckBw\iCjcH;weI9{cXN? MkXFNlUzOTN4N{C=
Hep3B MnH3SpVv[3Srb36gRZN{[Xl? NYXyUplDOSEQvF2= NW\DTos{OTZiaB?= NWPUXW5JTE2VTx?= NX7NN4EzUW2yYXny[ZMhfGinIHPhdIFkcXS7IH;mJGlJS0FvYYPzc4Nq[XSnZDDndFE{OCCvdYThcpR{KHSxIHHjeIl3\SCVVFHUN{B4cXSqIFnDOVAhd2ZifkWwJO69VQ>? NF3T[nIzPDVyMU[4PS=>
HepG2 NW\Wb2w{TnWwY4Tpc44hSXO|YYm= NH\VSFUyKM7:TR?= M1XFfVE3KGh? MXHEUXNQ NYnGU|JTUW2yYXny[ZMhfGinIHPhdIFkcXS7IH;mJGlJS0FvYYPzc4Nq[XSnZDDndFE{OCCvdYThcpR{KHSxIIPp[45idCC2bzDTWGFVOw>? NXi2VGxuOjR3MEG2PFk>
Huh7 NH7CS2hHfW6ldHnvckBCe3OjeR?= NYnJWmd{OSEQvF2= MUixOkBp NWTONZBZTE2VTx?= Ml3rTY1x[Wm{ZYOgeIhmKGOjcHHjbZR6KG:oIFnIR2Eu[XO|b3PpZZRm\CCpcEGzNEBufXSjboTzJJRwKHOrZ37hcEB1dyCVVFHUNy=> NWrlZ4JqOjR3MEG2PFk>
BaF3 Mo\5T4lv[XOnIFHzd4F6 MVW4NEBvVQ>? MYC2JIg> NYHnZpdrTE2VTx?= NUfke|ZQWmWmdXPld{B1cGVicHjvd5Bpd3K7bHH0bY9vKG:owrDTWGFVPSCrbjDKRWszXjZzN1[tcZV1[XSnZDDCRWY{NUWST2KgZ4VtdA>? MWeyOFI{Pzd7MR?=
DLD-1 Ml\ET4lv[XOnIFHzd4F6 M4PjTlI2KM7:TR?= NGPxZVQ1QCCq MkmzSG1UVw>? MWTJcohq[mm2aX;uJI9nKEqDS{GgdIhwe3Cqb4L5cIF1cW:w NED4boczPDB3MEW1NC=>
RKO NH;yPWhMcW6jc3WgRZN{[Xl? NYTiOWlHOjVizszN NX;jSFRVPDhiaB?= MVXEUXNQ NUXpTnF{UW6qaXLpeIlwdiCxZjDKRWsyKHCqb4PwbI9zgWyjdHnvci=> MWqyOFA2ODV3MB?=
DLD-1 NHvmNmdMcW6jc3WgRZN{[Xl? NFvoNGgzPSEQvF2= M2DGXFQ5KGh? MorNSG1UVw>? MVTJcohq[mm2aX;uJI9nKEqDS{KgdIhwe3Cqb4L5cIF1cW:w M3e5SlI1ODVyNUWw
RKO MYTLbY5ie2ViQYPzZZk> NH60ZlEzPSEQvF2= MYi0PEBp Ml7XSG1UVw>? NGrRe4Zld2W|IH7veEBqdmirYnn0JGpCUzFicHjvd5Bpd3K7bHH0bY9v NEeyOpIzPDB3MEW1NC=>
DLD-1 M1GwXWdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 M17qTVUxKM7:TR?= M1LwbVQ5KGh? NInYbFhFVVOR M1v4dWlEPTB;MUWuOVEh|ryP NGDxRmIzPDB3MEW1NC=>
RKO MYXHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NWjte2dZPTBizszN M{TQblQ5KGh? M4rXdmROW09? NIqwWJVKSzVyPUG0Mlc3KM7:TR?= NXPoXHVnOjRyNUC1OVA>
DLD-1 NX3sUJJ[SXCxcITvd4l{KEG|c3H5 MVGyOUDPxE1? MWm0PEBp NWDvPGd{TE2VTx?= MnXSTY5lfWOnczDhdI9xfG:|aYOgZpkh[WO2aY\heIlv\yClYYPwZZNmKDN? NGHudIozPDB3MEW1NC=>
RKO MWHBdI9xfG:|aYOgRZN{[Xl? NG\lOFgzPSEQvF2= MXu0PEBp M{C0bmROW09? MVPJcoR2[2W|IHHwc5B1d3OrczDifUBi[3SrdnH0bY5oKGOjc4Dhd4UhOw>? MkHONlQxPTB3NUC=
HuH7 NH3YXVdIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NFzaPG82OCEQvF2= MXu0PEBp NUPUeIZFTE2VTx?= MYS+PFImKHKnZIXjeIlwdg>? NUH5SYp2OjN7NEG4N|I>
SNU182 MUXHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NH7TNHo2OCEQvF2= M{S4XlQ5KGh? NH\WTHVFVVOR NIT4[mM,PjRnIILl[JVkfGmxbh?= NEmwb3AzOzl2MUizNi=>
SNU423 NVv3PYE2T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MVO1NEDPxE1? NH3EfGk1QCCq NHnGNZlFVVOR NIfBOGQ,QDFnIILl[JVkfGmxbh?= NWnJelVMOjN7NEG4N|I>
HuH7 NWHuWm1HTnWwY4Tpc44hSXO|YYm= MnjzOVAh|ryP NHn3cJczPCCq NX;0OVNKTE2VTx?= NHrBZpdKdmirYnn0bY9vKG:oIGPURXQyKGGwZDDTWGFVOyCyaH;zdIhwenmuYYTpc44he2mpbnnmbYNidnSueR?= NYjT[ol3OjN7NEG4N|I>
SNU182 NGiwSllHfW6ldHnvckBCe3OjeR?= NGSzZYE2OCEQvF2= NWK4[2lNOjRiaB?= NYDWOoNXTE2VTx?= Ml74TY5pcWKrdHnvckBw\iCVVFHUNUBidmRiU2TBWFMheGixc4Doc5J6dGG2aX;uJJNq\26rZnnjZY51dHl? NE\LOnQzOzl2MUizNi=>
SNU423 NF\WZoVHfW6ldHnvckBCe3OjeR?= MWG1NEDPxE1? NHntfJczPCCq M1jR[2ROW09? NHfiPIJKdmirYnn0bY9vKG:oIGPURXQyKGGwZDDTWGFVOyCyaH;zdIhwenmuYYTpc44he2mpbnnmbYNidnSueR?= NGPjW4EzOzl2MUizNi=>

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
cleaved PARP / cleaved caspase3; 

PubMed: 29849942     


OVCAR-8 and MDAH 2774 cells were incubated with various concentrations of ruxolitinib for 48 h. Apoptosis was determined by using cleaved poly-ADP ribose polymerase (PARP) and cleaved caspase-3 by Western blot.

p-JAK2 / p-AKT / p-MAPK / Bcl-xl / MCL-1; 

PubMed: 29849942     


OVCAR-8 and MDAH2774 cells were treated with ruxolitinib (20 μM), paclitaxel (10 nM) or the combination for 24 h. Whole cells were collected and determined for the change of STAT3, AKT and ERK pathways and expression of BCL-XL and MCL-1 by Western blot.

c-Myc / c-Jun / Cyclin B / Cyclin D / Bcl-2 / HIF-1α; 

PubMed: 30930994     


Effects of ruxolitinib on the expression of downstream target genes of the JAK-STAT pathway. The protein levels of c-Myc, c-Jun, Cyclin B1, Cyclin D1, Bcl-2 and HIF-1α were determined in MCF-7 and TAMR-MCF-7 cells 24 h following ruxolitinib treatment (0.1-10 μM). 

p-STAT3; 

PubMed: 29849942     


Dose-dependent inhibition of STAT3 phosphorylation. Human ovarian cancer cells, OVCAR-8, MDAH2774, and SKOV3, were treated with the indicated concentrations of ruxolitinib for 24 h. Phosphorylation of STAT3 was analyzed by Western blot. 

29849942 30930994
Growth inhibition assay
Cell viability; 

PubMed: 29849942     


Dose dependent inhibition of cell viability. Human ovarian cancer cell lines were treated with the indicated concentrations of ruxolitinib. Cell viability was determined 72 h later. The IC50 was determined by the Chou-Talalay method. *P<0.05; ***P<0.0005, ruxolitinib vs control in OVCAR-8 cells; #P<0.05; ##P<0.005; ###P<0.0005, ruxolitinib vs control in SKOV-3 cells; ^^P<0.005; ^^^P<0.0005, ruxolitinib vs control in MDAH2774 cells.

Cell apoptosis; 

PubMed: 29849942     


OVCAR-8 and MDAH 2774 cells were incubated with various concentrations of ruxolitinib for 48 h. Apoptosis was determined by flow cytometry using annexin V and PI staining.

Cell proliferation; 

PubMed: 29515770     


Cells were plated into 48 well plates and cell growth was measured every 48 hours via MTS assay following ruxolitinib treatment (0, 1, 10 and 100 uM) in L-428 (left) and HDLM-2 (middle) HL cells, and Karpas-1106P PMBL cells (right).

29849942 29515770
Immunofluorescence
α-tubulin; 

PubMed: 26356819     


Confocal analysis of HEL cells, treated or not with different concentration of ruxolitinib (100 and 300 nM), displaying α-Tubulin (green) and DAPI (blue) staining; MERGE shows the overlapped images. Scale bars are shown in the figure (10 μm). Note more diffuse microtubule networks in ruxolutinib-treated cells.

26356819
In vivo INCB018424 (180 mg/kg, orally, twice a day) results in survive rate of greater than 90% by day 22 in a JAK2V617F-driven mouse model. INCB018424 (180 mg/kg, orally, twice a day) markedly reduces splenomegaly and circulating levels of inflammatory cytokines, and preferentially eliminated neoplastic cells, resulting in significantly prolonged survival without myelosuppressive or immunosuppressive effects in a JAK2V617F-driven mouse model. [1] The primary end point is reached in 41.9% of patients in the Ruxolitinib group as compared with 0.7% in the placebo group in the double-blind trial of myelofibrosis. Ruxolitinib results in maintaining of reduction in spleen volume and improvement of 50% or more in the total symptom score. [2] A total of 28% of the patients in the Ruxolitinib (15 mg twice daily) group has at least a 35% reduction in spleen volume at week 48 in patients with myelofibrosis, as compared with 0% in the group receiving the best available therapy. The mean palpable spleen length has decreased by 56% with Ruxolitinib but has increased by 4% with the best available therapy at week 48. Patients in the ruxolitinib group has an improvement in overall quality-of-life measures and a reduction in symptoms associated with myelofibrosis. [3]

Protocol

Kinase Assay:[1]
+ Expand

Binding assay:

Recombinant proteins are expressed using Sf21 cells and baculovirus vectors and purified with affinity chromatography. JAK kinase assays use a homogeneous time-resolved fluorescence assay with the peptide substrate (-EQEDEPEGDYFEWLE). Each enzyme reaction is carried out with Ruxolitinib or control, JAK enzyme, 500 nM peptide, adenosine triphosphate (ATP; 1mM), and 2% dimethyl sulfoxide (DMSO) for 1 hour. The 50% inhibitory concentration (IC50) is calculated as INCB018424 concentration required for inhibition of 50% of the fluorescent signal.
Cell Research:[1]
+ Expand
  • Cell lines: Ba/F3 and HEL cells
  • Concentrations: 3 μM
  • Incubation Time: 48 hours
  • Method: Cells are seeded at 2 × 103/well of white bottom 96-well plates, treated with INCB018424 from DMSO stocks (0.2% final DMSO concentration), and incubated for 48 hours at 37 ℃ with 5% CO2. Viability is measured by cellular ATP determination using the Cell-Titer Glo luciferase reagent or viable cell counting. Values are transformed to percent inhibition relative to vehicle control, and IC50 curves are fitted according to nonlinear regression analysis of the data using PRISM GraphPad.
    (Only for Reference)
Animal Research:[1]
+ Expand
  • Animal Models: JAK2V617F-driven mouse model
  • Formulation: 5% dimethyl acetamide, 0.5% methocellulose
  • Dosages: 180 mg/kg
  • Administration: Oral gavage
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 61 mg/mL (199.1 mM)
Ethanol 61 mg/mL (199.1 mM)
Water Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
2% DMSO+30% PEG 300+ddH2O
For best results, use promptly after mixing.
5mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 306.37
Formula

C17H18N6

CAS No. 941678-49-5
Storage powder
in solvent
Synonyms N/A

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03774082 Not yet recruiting Drug: INC424 Graft vs Host Disease Novartis Pharmaceuticals|Novartis October 8 2019 Phase 2
NCT04057573 Not yet recruiting Drug: Ruxolitinib cream|Drug: Vehicle Non-segmental Vitiligo Incyte Corporation September 10 2019 Phase 3
NCT04052425 Not yet recruiting Drug: Ruxolitinib cream|Drug: Vehicle Non-segmental Vitiligo Incyte Corporation September 10 2019 Phase 3

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

Handling Instructions

Tel: +1-832-582-8158 Ext:3

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Frequently Asked Questions

  • Question 1:

    What is the difference between S2902 and S1378 which seem to have same structure formula according to the product information?

  • Answer:

    These two chemicals are the two different chiral forms of Ruxolitinib. S2902 S-Ruxolitinib is the S form and S1378 Ruxolitinib is the D form. One of the carbon atoms in this molecule is asymmetric, making the two molecules mirror images of each other. The biological activities of these two molecules can be very different because of the confirmation differences.

  • Question 2:

    How about the half-life of the compound (Ruxolitinib)? How long is the duration of the inhibitory effect on JAK-STAT signaling?

  • Answer:

    The half-life of this compound in body is about 2~3 hours according to previous study. Generally, it is longer in vitro culture medium than in vivo. In paper, Ruxolitinib was also used for 24hours. http://www.bloodjournal.org/cgi/pmidlookup?view=long&pmid=24711661.

JAK Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID