Upadacitinib hemihydrateProduct ingredient for Upadacitinib
- Name
- Upadacitinib hemihydrate
- Drug Entry
- Upadacitinib
Upadacitinib is an oral Janus kinase (JAK)1-selective inhibitor and a disease-modifying antirheumatic drug (DMARD) used in the treatment of rheumatoid arthritis to slow down disease progression. Rheumatoid arthritis is a chronic autoimmune inflammatory disease affecting the peripheral joints. It is characterized by synovial inflammation and hyperplasia, autoantibody production, cartilage damage and bone destruction, leading to co-morbidities.4 Despite a variety of therapeutic agents available for treatment, up to 40% of the patients do not respond to current therapies, including biological therapies.6 The etiology of the disease is mostly unknown; however, the role of JAK as a driver of immune-mediated conditions was discovered, leading to the use of JAK as therapeutic targets for rheumatoid arthritis.5 To reduce dose-related toxicity (as seen with some pan-JAK inhibitors) without significantly affecting efficacy, more selective JAK1 inhibitors, upadacitinib and filgotinib, were developed.4
The FDA approved upadacitinib in August 2019 and it is used for the treatment of active rheumatoid arthritis, psoriatic arthritis, atopic dermatitis, ulcerative colitis, and ankylosing spondylitis.9 In December 2019, it was additionally approved by the European Commission and Health Canada.10,15 Upadacitinib is marketed under the brand name RINVOQ for oral administration.9
- Accession Number
- DBSALT002885
- Structure
- Synonyms
- Upadacitinib hemihydrate / Upadacitinib hydrate
- UNII
- NEW4DV02U5
- CAS Number
- Not Available
- Weight
- Average: 778.765
Monoisotopic: 778.325052174 - Chemical Formula
- C34H40F6N12O3
- InChI Key
- GJMQTRCDSIQEFK-SCDRJROZSA-N
- InChI
- InChI=1S/2C17H19F3N6O.H2O/c2*1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15;/h2*3-6,10-11,21H,2,7-9H2,1H3,(H,24,27);1H2/t2*10-,11+;/m11./s1
- IUPAC Name
- bis((3S,4R)-3-ethyl-4-{1,5,7,10-tetraazatricyclo[7.3.0.0^{2,6}]dodeca-2(6),3,7,9,11-pentaen-12-yl}-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide) hydrate
- SMILES
- O.CC[C@@H]1CN(C[C@@H]1C1=CN=C2C=NC3=C(C=CN3)N12)C(=O)NCC(F)(F)F.CC[C@@H]1CN(C[C@@H]1C1=CN=C2C=NC3=C(C=CN3)N12)C(=O)NCC(F)(F)F
- External Links
- Predicted Properties
Property Value Source Water Solubility 0.0707 mg/mL ALOGPS logP 2.57 ALOGPS logP 0.85 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 13.99 Chemaxon pKa (Strongest Basic) 4.11 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 78.32 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 93.03 m3·mol-1 Chemaxon Polarizability 36.08 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon