Upadacitinib hemihydrate
[CAS# 2050057-56-0]

Identification

• Classification: API >> Antipyretic analgesics >> Non-steroidal anti-inflammatory drugs
• Name: Upadacitinib hemihydrate
• Synonyms: (3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide;hydrate
• Molecular Formula: C₃₄H₄₀F₆N₁₂O₃
• Molecular Weight: 778.75
• CAS Registry Number: 2050057-56-0
• SMILES: CC[C@@H]1CN(C[C@@H]1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F.CC[C@@H]1CN(C[C@@H]1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F.O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

Upadacitinib hemihydrate is a pharmaceutical compound recognized for its significant role in the treatment of various inflammatory and autoimmune conditions. It is a derivative of upadacitinib, a Janus kinase (JAK) inhibitor, and is used in its hemihydrate form to enhance its stability and efficacy.

The discovery of upadacitinib began with the search for effective JAK inhibitors. JAKs are enzymes involved in the signaling pathways of several cytokines, which are critical in the development of inflammatory diseases. Upadacitinib was developed as a selective inhibitor of JAK1, a subtype of the JAK family, aiming to offer targeted treatment with reduced side effects compared to non-selective JAK inhibitors. The hemihydrate form of upadacitinib was introduced to address issues related to the compound's solubility and stability, thereby improving its formulation and bioavailability.

The synthesis of upadacitinib hemihydrate involves the production of upadacitinib, followed by crystallization with water to form the hemihydrate. This process is carefully controlled to ensure that the hemihydrate form is achieved with high purity and stability. The presence of water molecules in the crystal lattice enhances the stability of the compound, making it more suitable for pharmaceutical formulations.

In clinical practice, upadacitinib hemihydrate is used for the treatment of rheumatoid arthritis, a chronic autoimmune disorder characterized by joint inflammation and pain. Its selective inhibition of JAK1 helps to modulate the immune response, reducing inflammation and improving symptoms. The drug has been shown to be effective in patients who do not respond adequately to conventional treatments, providing a new therapeutic option for managing the disease.

Beyond rheumatoid arthritis, upadacitinib hemihydrate is also explored for the treatment of other inflammatory conditions such as ulcerative colitis and ankylosing spondylitis. Its mechanism of action allows for targeted intervention in various inflammatory pathways, offering potential benefits in managing these chronic conditions.

The application of upadacitinib hemihydrate extends to ongoing research aimed at understanding its long-term effects and efficacy in different patient populations. Clinical studies continue to evaluate its safety profile, optimal dosing strategies, and effectiveness in combination with other therapies.

Overall, upadacitinib hemihydrate represents a significant advancement in the treatment of inflammatory diseases. Its development reflects ongoing efforts to improve the management of chronic conditions through targeted therapies with enhanced stability and efficacy.