PZ0017

Tofacitinib citrate

Name: Tofacitinib citrate
Brand: SIGMA

≥98% (HPLC), powder, JAK3 inhibitor

Synonym(s):

(3R,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile citrate salt, 3-[(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile citrate salt, CP-690550-10, Tasocitinib citrate salt

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₂₀N₆O · C₆H₈O₇

CAS Number:

540737-29-9

Molecular Weight:

504.49

UNSPSC Code:

12352200

PubChem Substance ID:

329823686

NACRES:

NA.77

MDL number:

MFCD11616529

Product Name

Tofacitinib citrate, ≥98% (HPLC)

SMILES string

OC(=O)CC(O)(CC(O)=O)C(O)=O.C[C@@H]1CCN(C[C@@H]1N(C)c2ncnc3[nH]ccc23)C(=O)CC#N

InChI

1S/C16H20N6O.C6H8O7/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16;7-3(8)1-6(13,5(11)12)2-4(9)10/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t11-,13+;/m1./s1

InChI key

SYIKUFDOYJFGBQ-YLAFAASESA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution; warmed)

storage temp.

room temp

Application

Tofacitinib citrate has been used:

as a ligand for human serum albumin in fluorescence quenching, dynamic light scattering (DLS) measurements, differential scanning calorimetry and molecular docking studies
as a medium supplement for full depth articular cartilage (FDC) explants to monitor cytokine-induced proteoglycan loss
as a Janus kinase inhibitor in MCF7 breast cancer cells

Biochem/physiol Actions

Tofacitinib is a potent inhibitor of Janus kinase 3 (JAK3) with some JAK-1 inhibitory activity as well. It blocks downstream STAT signaling resulting in potent inhibition of inflammatory cytokines with resultant immunosuppressive and anti-inflammatory activity. Tofacitinib is being investigated for for several autoimmune disorders including, rheumatoid arthritis, psoriasis and dry eye.

Tofacitinib is a potent inhibitor of Janus kinase 3 (JAK3).

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

General description

Tofacitinib is a synthetic molecule corresponding to a molecular weight of 312.4 Da and is permeable by transcellular diffusion.

Other Notes

Tofacitinib has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the Tofacitinib probe summary on the Chemical Probes Portal website.

pictograms

GHS08,GHS07

signalword

Warning

hcodes

H302,H361fd

pcodes

P202 - P264 - P280 - P301 + P312 - P308 + P313 - P405

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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The mechanism of action of tofacitinib-an oral Janus kinase inhibitor for the treatment of rheumatoid arthritis

Hodge JA, et al.

Clinical and Experimental Rheumatology, 34(2), 318-328 (2016)

Interferon-Stimulated Gene Expression as a Preferred Biomarker for Disease Activity in Aicardi-Goutières Syndrome.

Ben X Wang et al.

Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research, 37(4), 147-152 (2017-04-08)

Aicardi-Goutières syndrome (AGS) is an early-onset, genetic disease characterized by recurrent fever, multifocal lesions of the brain, and systemic autoimmunity. We report on 3 AGS patients, 2 siblings with an RNASEH2A gene mutation and 1 patient with a SAMHD1 gene

Dose-Dependent Pharmacokinetics of Tofacitinib in Rats: Influence of Hepatic and Intestinal First-Pass Metabolism.

Ji Sang Lee et al.

Pharmaceutics, 11(7) (2019-07-10)

This study investigated the pharmacokinetics of tofacitinib in rats and the effects of first-pass metabolism on tofacitinib pharmacokinetics. Intravenous administration of 5, 10, 20, and 50 mg/kg tofacitinib showed that the dose-normalized area under the plasma concentration-time curve from time

Phosphoproteome profiling reveals critical role of JAK-STAT signaling in maintaining chemoresistance in breast cancer

Nascimento AS, et al.

Testing, 8(70), 114756-114756 (2017)

Preformulation and Evaluation of Tofacitinib as a Therapeutic Treatment for Asthma.

Usir S Younis et al.

AAPS PharmSciTech, 20(5), 167-167 (2019-04-18)

Preformulation studies on tofacitinib citrate, a small molecule JAK3 specific inhibitor, have not been previously reported in literature. We therefore conducted several preformulation studies on tofacitinib citrate, and its free base, to better understand factors that affect its solubility, stability

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