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Filgotinib

CAS No.
1206161-97-8
Chemical Name:
Filgotinib
Synonyms
GLPG0634;GLPG634;SYN1158;CS-1083;GPLG0634;Feigotini;filgotinib;GLPG0634 >=95%;GLPG0634 (analog);GLPG0634;GLPG 0634
CBNumber:
CB52621138
Molecular Formula:
C21H23N5O3S
Molecular Weight:
425.5
MDL Number:
MFCD20527867
MOL File:
1206161-97-8.mol
MSDS File:
SDS
Last updated:2023-12-27 08:42:08

Filgotinib Properties

Melting point 229 - 231°C
Density 1.51±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility Soluble in DMSO (15 mg/ml with warming)
form solid
pka 8.04±0.20(Predicted)
color Off-white
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
FDA UNII 3XVL385Q0M

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H319-H315-H335
Precautionary statements  P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
HS Code  2921309990
NFPA 704
0
2 0

Filgotinib price More Price(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 17669 Filgotinib ≥98% 1206161-97-8 5mg $56 2024-03-01 Buy
Cayman Chemical 17669 Filgotinib ≥98% 1206161-97-8 1mg $25 2021-12-16 Buy
Cayman Chemical 17669 Filgotinib ≥98% 1206161-97-8 10mg $99 2024-03-01 Buy
Cayman Chemical 17669 Filgotinib ≥98% 1206161-97-8 25mg $166 2024-03-01 Buy
TRC G411100 GLPG-0634(Filgotinib) 1206161-97-8 25mg $200 2021-12-16 Buy
Product number Packaging Price Buy
17669 5mg $56 Buy
17669 1mg $25 Buy
17669 10mg $99 Buy
17669 25mg $166 Buy
G411100 25mg $200 Buy

Filgotinib Chemical Properties,Uses,Production

Description

Filgotinib (GLPG0634) is a selective JAK1 inhibitor with IC50 of 10 nM, 28 nM, 810 nM, and 116 nM for JAK1, JAK2, JAK3, and TYK2, respectively.

In vitro

In cell lines, GLPG0634 inhibits IL-2- and IL-4-induced JAK1/JAK3/γc signaling and IFN-αB2-induced JAK1/TYK2 type II receptor signaling with IC50 ranged from 150 to 760 nM. GLPG0634 shows higher selectivity for JAK/STAT signaling involving JAK1 than JAK2 kinase in a cellular context. Besides, GLPG0634 also inhibits the differentiation of Th1, Th2, and Th17 cells.

In vivo

Following oral administration, the absolute bioavailability is moderate in rats (45%) and high in mice (~100%). Filgotinib (30 mg/kg daily (Rats); 50 mg/kg twice daily (Mice)) dose-dependently reduces inflammation, cartilage, and bone degradation in the CIA model in rats and mice. Filgotinib (GLPG0634) in DSS-treated mice demonstrates that inhibition of JAK1 is sufficient for achieving strong efficacy in pre-clinical mouse model, correlated to the inhibition of STAT3 phosphorylation in the inflamed colon.

Description

Filgotinib is a JAK1 inhibitor (IC50 = 10 nM). It is selective for JAK1 over JAK3 (IC50 = 810 nM) but also inhibits JAK2 and tyrosine kinase 2 (Tyk2; IC50s = 28 and 116 nM, respectively), as well as Abl, FLT1, -3, and -4, FMS, Mer, and TBK1 activity by greater than 35% in a panel of 177 tyrosine kinases at 1 μM. Filgotinib inhibits IL-6-induced phosphorylation of STAT1 in CD4+ T cells with an IC50 value of 629 nM in isolated human whole blood. It reduces hind paw macrophage and T cell infiltration and bone erosion in a rat model of collagen-induced arthritis when administered at doses ranging from 0.1 to 30 mg/kg per day for 15 days.

Uses

GLPG-0634 (Filgotinib) is a potent, selective JAK1 inhibitor. Used as an anti-inflammatory agent, it reduces levels of inflammatory cytokines in the bones and tissue of mammals.

Mechanism of action

Filgotinib acts on the JAK-STAT pathway by selectively inhibiting JAK1 phosphorylation and preventing STAT activation, which ultimately results in reduced proinflammatory cytokine signaling.

Side effects

  • feeling sick (nausea)
  • upper respiratory tract infection
  • urinary tract infection.
  • dizziness.

Synthesis

The synthesis of Filgotinib is as follows:
With cyclopropanyl chloride in an amidated reaction in a system consisting of N-methylmorpholine and 1,4-dioxane,The amidation reaction time was 4 h,The amidation reaction temperature was 50 ° C,The molar ratio of the intermediate (III), cyclopropanyl chloride, N-methylmorpholine and 1,4-dioxane was 1: 2.8: 2.5:TLC plate to determine the reaction is completed, cooled to room temperature,Adding methylene chloride and water, separating the organic phase with water,Then washed with brine, dried over magnesium sulfate,Evaporated to dryness and the residue was purified over a silica gel column [elution solvent: ethyl acetate / n-hexane (3: 7 v / v)To obtain a solid yellowish solid,That is, Filgotinib, yield 91.2%.
synthesis of Filgotinib.png

References

Menet et al. (2014), Triazolopyridines as selective JAK1 inhibitors: from hit identification to GLPG0634; Med. Chem., 57 9323 Rompaey et al. (2013), Preclinical characterization of GLPG0634, a selective inhibitor of JAK1, for the treatment of inflammatory diseases; Immunol., 191 3568 Kavanaugh et al. (2017), Filgotinib (GLPG0634/GS-6034), an oral selective JAK1 inhibitor, is effective as monotherapy in patients with active rheumatoid arthritis: results from a randomized dose-finding study (DARWIN 2); Rheum. Dis., 76 1009 Wang et al. ?(2019), Oncostatin M inhibits differentiation of rat stem Leydig cells in vivo and in vitro; J. Cell. Mol. Med., 23 426

1257705-09-1
4023-34-1
1206161-97-8
Synthesis of Filgotinib from [1,2,4]Triazolo[1,5-a]pyridin-2-amine, 5-[4-[(1,1-dioxido-4-thiomorpholinyl)methyl]phenyl]- and Cyclopropanecarbonyl Chloride
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Related articles

  • How is Filgotinib synthesised?
  • Filgotinib is prepared using 2-aminopyridine as raw material by condensation, cyclisation, coupling and other reactions.
  • Dec 27,2023

View Lastest Price from Filgotinib manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
GLPG0634 pictures 2024-03-12 GLPG0634
1206161-97-8
US $0.00 / g 1g 98% HPLC 1kg shandong perfect biotechnology co.ltd
GLPG0634 ,Filgotinib  pictures 2023-06-26 GLPG0634 ,Filgotinib
1206161-97-8
US $150.00 / ASSAYS 10g more than 99.6% 500kg/month Hebei Mingeng Biotechnology Co., Ltd
GPLG0634 pictures 2022-02-18 GPLG0634
1206161-97-8
US $0.00 / gram 1gram 99% 10kg Zhejiang J&C Biological Technology Co.,Limited
  • GLPG0634 pictures
  • GLPG0634
    1206161-97-8
  • US $0.00 / g
  • 98% HPLC
  • shandong perfect biotechnology co.ltd
  • GPLG0634 pictures
  • GPLG0634
    1206161-97-8
  • US $0.00 / gram
  • 99%
  • Zhejiang J&C Biological Technology Co.,Limited

Filgotinib Spectrum

GPLG0634 SYN1158 CyclopropanecarboxaMide, N-[5-[4-[(1,1-dioxido-4-thioMorpholinyl)Methyl]phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl]- GLPG0634 (analog) N-[5-[4-[(1,1-Dioxido-4-thiomorpholinyl)methyl]phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide N-(5-(4-((1,1-Dioxidothiomorpholino)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide Filgotinib (GLPG0634) N-[5-[4-[(1,1-Dioxido-4-thiomorpholinyl)methyl]phenyl][1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide Filgotinib (GLPG0634) GLPG0634(filgotinib) GLPG634 N-(5-(4-((1,1-Dioxidothiomorpholino)methyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopro GLPG0634 >=95% GLPG0634;GLPG 0634;FILGOTINIB GPLG0634,filgotinib GLPG0634;GLPG 0634 CS-1083 N-(5-{4-[(1,1-Dioxidothiomorpholin-4-yl)methyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (2Z)-but-2-enedioate GPLG0634 USP/EP/BP GLPG0634 filgotinib Feigotini cyclopropanecarboxylic acid {5-[ 4-(1,1-dioxo-thiomorpholin-4-ylmethyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide GLPG 0634,GLPG-0634,inhibit,Janus kinase,JAK,Filgotinib,Inhibitor N-[5-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide 1206161-97-8 Inhibitors API 1206161-97-8