-Tofacitinib Chemical Structure.png)
(3R,4S)-Tofacitinib (Tofacitinib Impurity A) is a less active diastereomer/enantiomer of Tofacitinib (CP 690550; tasocitinib; Xeljanz), which is a JAK3 (Janus-Associated kinase) inhibitor 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 | 312.169 |
| Elemental Analysis | C, 61.52; H, 6.45; N, 26.90; O, 5.12 |
| CAS # | 1092578-46-5 |
| Related CAS # | Tofacitinib;477600-75-2;Tofacitinib citrate;540737-29-9;(3S,4S)-Tofacitinib;1092578-47-6;(3S,4R)-Tofacitinib;1092578-48-7 |
| PubChem CID | 25180101 |
| Appearance | White to off-white solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 585.8±50.0 °C at 760 mmHg |
| Flash Point | 308.1±30.1 °C |
| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
| Index of Refraction | 1.646 |
| LogP | 0.93 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 23 |
| Complexity | 488 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C[C@H]1CCN(C[C@@H]1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N |
| InChi Key | UJLAWZDWDVHWOW-AAEUAGOBSA-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-[(3R,4S)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile |
| Synonyms | Tofacitinib Impurity A; (3R,4S)-Tofacitinib; 1092578-46-5; 3-((3R,4S)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; B64WR5WNB7; Epitofacitinib, (3R,4S)-; CHEMBL457871; 3-[(3R,4S)-4-METHYL-3-[METHYL(7H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)AMINO]PIPERIDIN-1-YL]-3-OXOPROPANENITRILE; (3R,4S)-(+)-Tofacitinib isomer; |
| 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; less active diastereomer/enantiomer of Tofacitinib |
| ln Vitro | (3R,4S)-Tofacitinib is an impurity of Tofacitinib and is a less active diastereomer of Tofacitinib. |
| References | [1]. https://pubchem.ncbi.nlm.nih.gov/compound/25180101 |
| Additional Infomation | (3r,4s)-Tofacitinib is a N-acylpiperidine. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~320.13 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 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. (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 |