CP 690550 citrate

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Cat.No. 4556 - CP 690550 citrate | C16H20N6O.C6H8O7 | CAS No. 540737-29-9
Description: Potent JAK inhibitor
Alternative Names: Tofacitinib citrate
Chemical Name: (3R,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile citrate
Purity: ≥99% (HPLC)
Datasheet
Citations (2)
Reviews (1)
Literature
Pathways

Biological Activity

Potent JAK inhibitor (IC50 values are 1, 20, and 112 nM for JAK3, JAK2 and JAK1 respectively). Orally active immunosuppressant; exhibits efficacy in rodent rheumatoid arthritis models.

Licensing Information

Sold for research purposes under agreement from Pfizer Inc.

External Portal Information

Chemicalprobes.org is a portal that offers independent guidance on the selection and/or application of small molecules for research. The use of CP 690550 (Tofacitinib) is reviewed on the chemical probes website.

Compound Libraries

CP 690550 citrate is also offered as part of the Tocriscreen Plus and Tocriscreen Kinase Inhibitor Toolbox II. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 504.49
Formula C16H20N6O.C6H8O7
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 540737-29-9
PubChem ID 10174505
InChI Key SYIKUFDOYJFGBQ-YLAFAASESA-N
Smiles C[C@H]1[C@@H](N(C2=NC=NC3=C2C=CN3)C)CN(C(CC#N)=O)CC1.OC(CC(O)=O)(C(O)=O)CC(O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.45 100

Preparing Stock Solutions

The following data is based on the product molecular weight 504.49. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.98 mL 9.91 mL 19.82 mL
5 mM 0.4 mL 1.98 mL 3.96 mL
10 mM 0.2 mL 0.99 mL 1.98 mL
50 mM 0.04 mL 0.2 mL 0.4 mL

Molarity Calculator

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References

References are publications that support the biological activity of the product.

Jiang et al (2008) Examining the chirality, conformation and selective kinase inhibition of 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile (CP-690,550). J.Med.Chem. 51 8012 PMID: 19053756

Flanagan et al (2010) Discovery of CP-690,550: a potent and selective Janus kinase (JAK) inhibitor for the treatment of autoimmune diseases and organ transplant rejection. J.Med.Chem. 53 8468 PMID: 21105711

Dowty et al (2013) Preclinical to clinical translation of tofacitinib, a Janus kinase inhibitor, in rheumatoid arthritis. J.Pharmacol.Exp.Ther. 348 165 PMID: 24218541


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2 Citations for CP 690550 citrate

Citations are publications that use Tocris products. Selected citations for CP 690550 citrate include:

Tactacan et al (2015) The pseudokinase SgK223 promotes invasion of pancreatic ductal epithelial cells through JAK1/Stat3 signaling. Mol Cancer 14 139 PMID: 26215634

Zhu et al (2015) Adenosine 5'-monophosphate-activated protein kinase regulates IL-10-mediated anti-inflammatory signaling pathways in macrophages. Nat Commun 194 584 PMID: 25512602


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Reviews for CP 690550 citrate

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Worked for cytokine Elisa analysis: Excellent publishable, performed ideally.
By Scott Scarneo on 02/06/2019
Assay Type: Ex Vivo
Species: Human
Cell Line/Tissue: RA FLS

Used for RA FLS Cytokine production of IL-6.

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Literature in this Area

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Kinases Product Listing

A collection of over 400 products for kinase research, the listing includes inhibitors of:

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Pathways for CP 690550 citrate

JAK-STAT

JAK-STAT Signaling Pathway

The JAK-STAT signaling pathway has several roles, including the control of cell proliferation and hematopoiesis. It is the main signal transduction cascade from cytokine receptors.