MedKoo Cat#: 200811 Name: Tofacitinib CAS#: 477600-75-2 (free base) Chemical Formula: C16H20N6O Exact Mass: 312.16986 Molecular Weight: 312.37 Elemental Analysis: C, 61.52; H, 6.45; N, 26.90; O, 5.12

Related CAS #: 540737-29-9 (citrate) 477600-75-2 (free base)

Synonym: Tofacitinib free baseCP690550; CP-690550; CP 690550; Tofacitinib; tasocitinib. Trade name Xeljanz

IUPAC/Chemical Name: 3-((3R,4R)-4-Methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile

InChi Key: UJLAWZDWDVHWOW-YPMHNXCESA-N

InChi Code: InChI=1S/C16H20N6O/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/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/m1/s1

SMILES Code: N#CCC(N1C[C@H](N(C)C2=C3C(NC=C3)=NC=N2)[C@H](C)CC1)=O

Technical Data

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Certificate of Analysis: View CoA: previous batch, Lot#LC20130315 View CoA: current batch, Lot#BBC60914

QC Data: View QC data: current batch, Lot#BBC60914

Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

Additional Information

It is an inhibitor of the enzyme janus kinase 3 (JAK3), which means that it interferes with the JAK-STAT signaling pathway, which transmits extracellular information into the cell nucleus, influencing DNA transcription. Recently it has been shown in a murine model of established arthritis that tofacitinib rapidly improved disease by inhibiting the production of inflammatory mediators and suppressing STAT1-dependent genes in joint tissue. This efficacy in this disease model correlated with the inhibition of both JAK1 and 3 signaling pathways, suggesting that tofacitinib may exert therapeutic benefit via pathways that are not exclusive to inhibition of JAK3.    

References

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