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Merck

PZ0017

Sigma-Aldrich

Tofacitinib citrate

≥98% (HPLC), powder, JAK3 inhibitor

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C16H20N6O · C6H8O7
Número de CAS:
Peso molecular:
504.49
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

Nombre del producto

Tofacitinib citrate, ≥98% (HPLC)

Nivel de calidad

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to beige

solubilidad

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

temp. de almacenamiento

room temp

cadena SMILES

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

Clave InChI

SYIKUFDOYJFGBQ-YLAFAASESA-N

Información sobre el gen

Descripción general

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

Aplicación

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

Acciones bioquímicas o fisiológicas

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).

Características y beneficios

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.

Otras notas

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.

Pictogramas

Health hazardExclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral - Repr. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Visite la Librería de documentos

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)
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
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
Tofacitinib and TPCA-1 exert chondroprotective effects on extracellular matrix turnover in bovine articular cartilage ex vivo
Kjelgaard-Petersen CF, et al.
Biochemical Pharmacology (2018)
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)

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