Ruxolitinib phosphateProduct ingredient for Ruxolitinib
- Name
- Ruxolitinib phosphate
- Drug Entry
- Ruxolitinib
Ruxolitinib, formerly known as INCB018424 or INC424, is an anticancer drug and a Janus kinase (JAK) inhibitor. It is a potent and selective inhibitor of JAK1 and JAK2,3 which are tyrosine kinases involved in cytokine signalling and hematopoiesis.2 Myeloproliferative neoplasms, such as myelofibrosis and polycythemia vera, are often characterized by aberrant activation of the JAK-STAT pathway, leading to abnormal blood cell counts and thrombotic complications. By inhibiting JAK1 and JAK2, ruxolitinib works to block the dysregulated cell signalling pathways and prevents abnormal blood cell proliferation.5 Due to a large number of patients with myeloproliferative neoplasms who have JAK2 mutations, ruxolitinib was the first ATP-competitive inhibitor of JAK1 and JAK2 ever developed.15
Ruxolitinib was first approved for the treatment of adult patients with myelofibrosis by the FDA in 2011, followed by EMA's approval in 2012.5 In 2014, it was approved for the treatment of polycythemia vera in adults who have an inadequate response to or are intolerant of hydroxyurea and in 2019, ruxolitinib was approved for use in steroid-refractory acute graft-versus-host disease in adults and children.19 The topical formulation of ruxolitinib is used to treat atopic dermatitis and vitiligo.23 It is being investigated for other inflammatory skin conditions.12
Ruxolitinib has been investigated to treat patients with coronavirus disease 2019 (COVID-19) accompanied by severe systemic hyperinflammation. In phase II clinical trials, ruxolitinib improved chest computed tomography and improved recovery in patients with lymphopenia.6,7 However, phase III clinical trials later determined that ruxolitinib was inadequate in meeting its primary endpoint of reducing the number of hospitalized COVID-19 patients who experienced severe complications 20 thus the drug was not approved as a treatment for COVID-19.
- Accession Number
- DBSALT000156
- Structure
Structure for Ruxolitinib phosphate (DBSALT000156)
- Synonyms
- Not Available
- UNII
- 436LRU32H5
- CAS Number
- 1092939-17-7
- Weight
- Average: 404.3602
Monoisotopic: 404.136189702 - Chemical Formula
- C17H21N6O4P
- InChI Key
- JFMWPOCYMYGEDM-XFULWGLBSA-N
- InChI
- InChI=1S/C17H18N6.H3O4P/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16;1-5(2,3)4/h6,8-12,15H,1-5H2,(H,19,20,21);(H3,1,2,3,4)/t15-;/m1./s1
- IUPAC Name
- (3R)-3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile; phosphoric acid
- SMILES
- OP(O)(O)=O.[H][C@@](CC#N)(C1CCCC1)N1C=C(C=N1)C1=C2C=CN=C2NC=N1
- External Links
- PubChem Compound
- 25127112
- ChemSpider
- 26286920
- ChEBI
- 66917
- ChEMBL
- CHEMBL1795071
- Wikipedia
- Ruxolitinib
- Predicted Properties
Property Value Source Water Solubility 0.258 mg/mL ALOGPS logP 2.1 ALOGPS logP 1.99 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 11.57 Chemaxon pKa (Strongest Basic) 5.24 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 83.18 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 97.38 m3·mol-1 Chemaxon Polarizability 33.1 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon