Tofacitinib

Base Information

• Chemical Name: Tofacitinib
• CAS No.: 477600-75-2
• Molecular Formula: C16H20N6O
• Molecular Weight: 312.37
• Hs Code.: 29335990
• European Community (EC) Number: 689-145-4
• UNII: 87LA6FU830
• DSSTox Substance ID: DTXSID90197271
• Nikkaji Number: J2.740.060D
• Wikipedia: Tofacitinib
• Wikidata: Q3530324
• NCI Thesaurus Code: C95800
• RXCUI: 1357536
• Pharos Ligand ID: MP4M7KJWPRGV
• Metabolomics Workbench ID: 65509
• ChEMBL ID: CHEMBL221959
• Mol file: 477600-75-2.mol

Synonyms:CP 690,550;CP 690550;CP-690,550;CP-690550;CP690550;tasocitinib;tofacitinib;tofacitinib citrate;Xeljanz

Chemical Property of Tofacitinib

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.646
• Boiling Point: 585.845 °C at 760 mmHg
• PKA: 6.04±0.60(Predicted)
• Flash Point: 308.108 °C
• PSA: 88.91000
• Density: 1.296 g/cm³
• LogP: 1.48268
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 100 mg/ml).
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 312.16985928
• Heavy Atom Count: 23
• Complexity: 488

Purity/Quality:

99% ^*data from raw suppliers

Tofacitinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antirheumatic Agents
• Canonical SMILES: CC1CCN(CC1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
• Isomeric SMILES: C[C@@H]1CCN(C[C@@H]1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
• Recent ClinicalTrials: Mesothelin-Targeted Immunotoxin LMB-100 in Combination With Tofacitinib in Persons With Previously Treated Pancreatic Adenocarcinoma, Cholangiocarcinoma and Other Mesothelin Expressing Solid Tumors
• Recent EU Clinical Trials: A Randomised Pilot Study of the Safety and Efficacy of Tofacitinib (Xeljanz) in Improving Endoscopic Outcomes in Subjects with Ulcerative Colitis with Active, Chronic, Antibiotic Dependent or Refractory Idiopathic Pouchitis
• Recent NIPH Clinical Trials: Evaluation of Oral Tofacitinib in Children Aged 2 to 17 Years Old Suffering From Moderate to Severe Ulcerative Colitis
• Description: In November 2012, the US FDA approved tofacitinib (also referred to as CP-690550) for the treatment of adult patients with moderate to severely active rheumatoid arthritis (RA) who have had an inadequate response or intolerance to methotrexate. Tofacitinib is the first small molecule kinase inhibitor approved for the treatment of RA. Tofacitinib is an inhibitor of the four subtypes of Janus kinase (JAK): JAK1, JAK2, JAK3, and Tyk2. The JAKs are intracellular, nonreceptor tyrosine kinases that play important roles in the signal transduction pathway of many cytokines (e.g., interleukins 2, 4, 7, 9, 15, and 21) and are involved in the propagation of inflammation in RA. Tofacitinib acts by inhibiting the phosphorylation and activation of signal transducers and activators of transcription (STATs), thereby suppressing the production of inflammatory mediators in joint tissue. At the enzyme level, tofacitinib inhibits JAKs 1, 2, 3, and Tyk2 with IC50s of 3.2, 4.1, 1.6, and 34 nM, respectively. At the cellular level, tofacitinib inhibits the in vitro activities of JAK1/JAK2, JAK1/JAK3, and JAK2/JAK2 combinations with IC50s of 406, 56, and 1377 nM, respectively.
• Uses: CP-690550 is a pyrrolo[2,3-d]pyrimidine derivative, as Janus kinase inhibitor for treatment of rheumatoid arthritis
• Indications: The JAK family includes four isoforms, JAK1, JAK2, JAK3, and tyrosine kinase (TYK2). Ruxolitinib (Jakafi(R), Incyte Corp.) was the first approved JAK inhibitor, which inhibits both JAK1 and JAK2, used for the treatment of different types of myelofibrosis. Tofacitinib (Xeljanz(R), Pfizer) was approved by FDA as a JAK3-selective inhibitor for the treatment of rheumatoid arthritis and is one of the only two FDA-approved kinase inhibitors for non-oncological indications.