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Key Documents

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SML2393

Sigma-Aldrich

XL019

≥98% (HPLC)

Sinónimos:

(2S)-N-[4-[2-[[4-(4-Morpholinyl)phenyl]amino]-4-pyrimidinyl]phenyl]-2-pyrrolidinecarboxamide, (S)-N-(4-(2-(4-Morpholinophenylamino)pyrimidin-4-yl)phenyl)pyrrolidine-2-carboxamide, N-(4-{2-[(4-Morpholin-4-ylphenyl)amino]pyrimidin-4-yl}phenyl)-L-prolinamide

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About This Item

Fórmula empírica (notación de Hill):
C25H28N6O2
Número de CAS:
945755-56-6
Peso molecular:
444.53
MDL number:
MFCD24386874
UNSPSC Code:
12352200

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL

storage temp.

2-8°C

SMILES string

O=C(NC1=CC=C(C=C1)C2=NC(NC3=CC=C(C=C3)N4CCOCC4)=NC=C2)[C@H]5NCCC5

InChI

1S/C25H28N6O2/c32-24(23-2-1-12-26-23)28-19-5-3-18(4-6-19)22-11-13-27-25(30-22)29-20-7-9-21(10-8-20)31-14-16-33-17-15-31/h3-11,13,23,26H,1-2,12,14-17H2,(H,28,32)(H,27,29,30)/t23-/m0/s1

InChI key

ISOCDPQFIXDIMS-QHCPKHFHSA-N

Biochem/physiol Actions

XL019 is an ATP-binding site-targeting, orally active JAK2 subtype-selective Janus kinase inhibitor (IC50 in nM = 2.2/JAK2 vs. 134.3/JAK1, 214.2/JAK3, 348.3/TYK2) with much reduced or little activity against 116 other kinases (IC50 in nM = 125.4/PDGFRB, 139.7/FLT3, 225.8/c-KIT, 313.8/p70S6K, 370/MLK1, 375.4/IKKbeta, 483.6/KDR, 546.7/PDGFRA, 554.5/FLT4, 910.5/FLT; IC50 >1 μM toward remaining 106 kinases), CYP (1A2, 2C9, 2D6, 3A4 IC50 ≥20 μM), hERG (IC50 = 16 μM), and P-glycoprotein (IC50 >20 μM). XL019 effectively inhibits cellular STAT1/STAT3 phosphorylation both in HEL92.1.7 cultures (IC50 in nM = 386.4/pStat1 and 695/pStat3) and in HEL92.1.7 xenograft-derived tumor in mice in vivo (oral ED50 in mg/kg = 42/pStat1 and 210/pStat3) with significant HEL92.1.7 tumor suppression efficacy in mice (by 60% and 70% on day 14, respectively, with 200 and 300 mg/kg bid p.o. dosage).

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1 Oral

target_organs

Central nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Timothy Forsyth et al.
Bioorganic & medicinal chemistry letters, 22(24), 7653-7658 (2012-11-07)
We report the discovery of a series of 4-aryl-2-aminoalkylpyrimidine derivatives as potent and selective JAK2 inhibitors. High throughput screening of our in-house compound library led to the identification of hit 1, from which optimization resulted in the discovery of highly
Charles G Mullighan et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(23), 9414-9418 (2009-05-28)
Pediatric acute lymphoblastic leukemia (ALL) is a heterogeneous disease consisting of distinct clinical and biological subtypes that are characterized by specific chromosomal abnormalities or gene mutations. Mutation of genes encoding tyrosine kinases is uncommon in ALL, with the exception of
Marilyn M Giacomini et al.
Drug metabolism and disposition: the biological fate of chemicals, 45(1), 76-85 (2016-11-03)
Inhibition of thiamine transporters has been proposed as a putative mechanism for the observation of Wernicke's encephalopathy and subsequent termination of clinical development of fedratinib, a Janus kinase inhibitor (JAKi). This study aimed to determine the potential for other JAKi

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