-Tofacitinib Chemical Structure.png)
(3S,4S)-Tofacitinib (Tofacitinib Impurity C) is a less active enantiomer of Tofacitinib (tasocitinib; CP-690550; Xeljanz), which is an inhibitor of JAK3 (Janus-Associated kinase) and an FDA approved drug for the treatment of rheumatoid arthritis (RA), psoriatic arthritis, and ulcerative colitis.
Physicochemical Properties
| Molecular Formula | C16H20N6O |
| Molecular Weight | 312.3696 |
| Exact Mass | 312.17 |
| Elemental Analysis | C, 61.52; H, 6.45; N, 26.90; O, 5.12 |
| CAS # | 1092578-47-6 |
| Related CAS # | Tofacitinib;477600-75-2;Tofacitinib citrate;540737-29-9;(3R,4S)-Tofacitinib;1092578-46-5;(3S,4R)-Tofacitinib;1092578-48-7 |
| PubChem CID | 20111936 |
| Appearance | Off-white to pink solid powder |
| LogP | 1.482 |
| SMILES | C[C@H]1CCN(C[C@H]1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N |
| InChi Key | UJLAWZDWDVHWOW-WCQYABFASA-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+/m0/s1 |
| Chemical Name | 3-[(3S,4S)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile |
| Synonyms | (3S,4S)-Tofacitinib; 1092578-47-6; 3-((3S,4S)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; (-)-Tofacitinib; C3EP7ZZ9UQ; Tofacitinib, (3S,4S)-; CHEMBL459769; 3-[(3S,4S)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile; |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets | JAK3; S-enantiomer of Tofacitinib, less active |
| ln Vitro | (3S,4S)-Tofacitinib is an impurity and the diasteromer of Tofacitinib, and is less active than Tofacitinib. |
| References | [1]. https://pubchem.ncbi.nlm.nih.gov/compound/20111936 |
Solubility Data
| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~320.13 mM) H2O : ~0.67 mg/mL (~2.14 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (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 |