| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Impurity of Tofacitinib
The primary target of (3S,4R)-Tofacitinib is the Janus kinase (JAK) family, particularly JAK3. JAK3 is a tyrosine kinase that associates with the common gamma chain of cytokine receptors and mediates signaling through IL-2, IL-4, IL-7, IL-9, IL-15, and IL-21. (3S,4R)-Tofacitinib is the less active enantiomer of tofacitinib and exhibits reduced potency compared to the active enantiomer. |
|---|---|
| ln Vitro |
(3S,4R)-Tofacitinib is a Tofacitinib Impurity and is less active against JAK3.
In vitro, (3S,4R)-Tofacitinib exhibits reduced potency compared to the active enantiomer of tofacitinib. Tofacitinib inhibits JAK3 with an IC50 of 1 nM and is 20- to 100-fold less potent against JAK2 and JAK1. The (3S,4R) enantiomer is used as a negative control in JAK inhibitor assays to demonstrate stereoselective activity. It is a reference standard for chiral analysis. |
| ln Vivo |
In vivo activity data for (3S,4R)-Tofacitinib are limited in public literature. As the less active enantiomer, it would be expected to show reduced efficacy compared to the active enantiomer in animal models of autoimmune diseases. However, detailed pharmacokinetic and efficacy data are not extensively reported. It remains a research tool for studying JAK inhibitor stereoselectivity.
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| Enzyme Assay |
For non-cellular kinase assays, recombinant JAK3 is incubated with a peptide substrate and ATP in kinase buffer. Serial dilutions of (3S,4R)-Tofacitinib are added, and the reaction is incubated at 30°C for 30-60 minutes. ADP production is measured using the ADP-Glo Kinase Assay kit. IC50 values are determined and compared to the active enantiomer to assess stereoselectivity.
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| Cell Assay |
For cell-based assays, JAK3-dependent cell lines (e.g., CTLL-2) are cultured and treated with serial dilutions of (3S,4R)-Tofacitinib. Cell proliferation is measured by [3H]-thymidine incorporation or MTT assay. STAT5 phosphorylation is assessed by Western blot. The compound is used as a negative control in JAK inhibitor studies.
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| Animal Protocol |
For in vivo experiments, (3S,4R)-Tofacitinib would be administered to rodents in models of autoimmune disease (e.g., collagen-induced arthritis) via oral gavage. However, as the less active enantiomer, it is primarily used as a reference standard rather than for in vivo efficacy studies.
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| References |
[1]. https://pubchem.ncbi.nlm.nih.gov/compound/9966538
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| Molecular Formula |
C16H20N6O
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|---|---|
| Molecular Weight |
312.3696
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| Exact Mass |
312.17
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| CAS # |
1092578-48-7
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| Related CAS # |
Tofacitinib;477600-75-2;Tofacitinib citrate;540737-29-9;(3S,4S)-Tofacitinib;1092578-47-6;(3R,4S)-Tofacitinib;1092578-46-5
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| PubChem CID |
9966538
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| Appearance |
White to light yellow solid
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| LogP |
1.482
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
23
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| Complexity |
488
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CN(C1=NC=NC2=C1C=CN2)[C@H]3[C@H](C)CCN(C(CC#N)=O)C3
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| InChi Key |
UJLAWZDWDVHWOW-DGCLKSJQSA-N
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| 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
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| Chemical Name |
3-[(3S,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile
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| Synonyms |
Tofacitinib Impurity B; (3S,4R)-Tofacitinib; 1092578-48-7; 3-((3S,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; 3-[(3s,4r)-4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile; D2E2X7QH4A; Epitofacitinib, (3S,4R)-; CHEMBL459977; (3S,4R)-(-)-Tofacitinib isomer;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~320.1 mM; with ultrasonication)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2013 mL | 16.0067 mL | 32.0133 mL | |
| 5 mM | 0.6403 mL | 3.2013 mL | 6.4027 mL | |
| 10 mM | 0.3201 mL | 1.6007 mL | 3.2013 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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