Apixaban | Factor Xa Inhibitor | CAS 503612-47-3 | Anticoagulant
Product Name: Apixaban
CAS No.: 503612-47-3
Molecular Formula: C₂₅H₂₅N₅O₄
Appearance: White or almost white powder
Solubility: Practically insoluble in water; sparingly soluble in ethanol; freely soluble in DMSO
1. Introduction
Apixaban is an oral, direct, selective Factor Xa inhibitor. It is used for the prevention of venous thromboembolic events (VTE) in adult patients after elective hip or knee replacement surgery, for the prevention of stroke and systemic embolism in patients with non-valvular atrial fibrillation (NVAF), and for the treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE) as well as the prevention of their recurrence.
Factor Xa plays a key role in the coagulation cascade, catalyzing the conversion of prothrombin to thrombin. Direct Factor Xa inhibitors, such as apixaban, represent a new class of oral anticoagulants that provide a predictable anticoagulant effect without the need for routine coagulation monitoring (unlike warfarin). Apixaban has demonstrated high efficacy and a favorable safety profile in numerous clinical trials.
2. Chemical Structure & Synthesis
Apixaban is a pyrazolopyridine derivative. Its structure is optimized for selective binding to the active site of Factor Xa.
Molecular Formula: C₂₅H₂₅N₅O₄
The synthesis of apixaban is a complex multi-step process involving the construction of heterocyclic rings and the introduction of specific functional groups that ensure high affinity and selectivity for Factor Xa.
3. Physicochemical Properties & Pharmacology
| Property | Description |
|---|---|
| Appearance | White or almost white powder |
| Solubility | Practically insoluble in water; sparingly soluble in ethanol; freely soluble in DMSO |
| Mechanism of Action | Potent, reversible, direct, and highly selective inhibitor of the active site of Factor Xa. Inhibits both free and clot-bound Factor Xa, as well as prothrombinase activity. Inhibition of Factor Xa interrupts both the intrinsic and extrinsic coagulation cascade pathways, preventing thrombin generation and thrombus formation |
| Absorption | Rapidly absorbed orally; bioavailability ≈50% |
| tₘₐₓ | 3–4 hours |
| Metabolism | Hepatic (primarily CYP3A4/5) |
| Excretion | Feces (predominantly) and urine |
| Half-life (T½) | ≈12 hours |
4. Applications
| Indication | Use |
|---|---|
| VTE Prophylaxis | After elective hip or knee replacement surgery |
| Stroke Prevention | In adult patients with non-valvular atrial fibrillation (NVAF) with one or more risk factors |
| DVT & PE Treatment | Treatment of deep vein thrombosis and pulmonary embolism |
| Recurrence Prevention | Prevention of recurrent DVT and PE |
5. Conclusion
Apixaban is one of the leading representatives of the new generation of oral anticoagulants, which has significantly expanded the possibilities for the prevention and treatment of thromboembolic complications. Its predictable pharmacokinetics, lack of need for routine laboratory monitoring, and favorable efficacy-safety ratio make it the preferred choice in many clinical situations. However, as with any anticoagulant, it is necessary to carefully assess bleeding risk and consider possible drug interactions.
