Apixaban Impurities and Apixaban
Daicel Pharma synthesizes high-quality Apixaban impurities, including N-Formyl-1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxamide, ethyl 6-(4-(5-chloropentanamido)phenyl-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate, ethyl 1-(4-methoxyphenyl)-7a-morpholino-6-(4-nitrophenyl)-7-oxo3a,4,5,6,7,7a-hexahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate, and so on. These impurities are essential for evaluating the quality, stability, and safety of Apixaban, which is an active pharmaceutical ingredient. Additionally, Daicel Pharma offers a customized synthesis of Apixaban impurities for global delivery to meet the specific needs of our customers.
Apixaban [CAS: 503612-47-3] is an oral anticoagulant that selectively inhibits factor Xa. Apixaban blocks the conversion of prothrombin to thrombin, and prevents the formation of cross-linked fibrin clots.
Apixaban: Use and Commercial Availability
Apixaban is a medication and belongs to the class of novel oral anticoagulants (NOACs). It is available under the brand name Eliquis. This medication has multiple approved indications, including reducing the risk of stroke and systemic embolism in patients with non-valvular atrial fibrillation. It also treats deep vein thrombosis (DVT) and pulmonary embolism (PE) and prevents DVT in patients undergoing knee or hip replacement surgery. Additionally, Apixaban helps reduce the risk of recurrent DVT and PE. Overall, Apixaban is a versatile medication that inhibits blood clotting factors, reducing the risk of potentially serious complications associated with various medical conditions.
Apixaban Structure and Mechanism of Action
The chemical name of Apixaban is 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1-piperidinyl)phenyl]-1H-pyrazolo[3,4-c]pyridine-3-carboxamide. Its chemical formula is C25H25N5O4, and its molecular weight is approximately 459.5 g/mol.
Apixaban inhibits prothrombinase activity and clot-bound Fxa. It decreases thrombin generation and thrombus development.
Apixaban Impurities and Synthesis
As with any medication, Apixaban may contain impurities that affect its safety and efficacy. Impurities can be generated during the synthesis1 and storage of the drug. Apixaban impurities can include related compounds that may have similar chemical and physical properties as the active pharmaceutical ingredient (API) and degradation products that result from chemical or external changes in the drug over time. Apixaban impurities may also include residual solvents, reagents, or other substances used during the manufacturing process. It is essential to synthesize and analyze Apixaban impurities in the API to ensure the medication is safe and effective for patients.
Daicel Pharma provides a Certificate of Analysis (CoA) for Apixaban impurity standards, including N-Formyl-1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxamide, ethyl 6-(4-(5-chloropentanamido)phenyl-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate, ethyl 1-(4-methoxyphenyl)-7a-morpholino-6-(4-nitrophenyl)-7-oxo3a,4,5,6,7,7a-hexahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate, and so on. The CoA is generated from a cGMP-compliant analytical facility and includes comprehensive characterization data such as 1H NMR, 13C NMR, IR, MASS, and HPLC purity2. We can also give additional characterization data like 13C-DEPT and CHN on request. Daicel Pharma is capable of preparing unknown Apixaban impurities or degradation products. Each delivery has a complete characterization report.
- Pinto, Donald; Quan, Mimi; Orwat, Michael; Li, Yun-Long; Han, Wei; Qiao, Jennifer; Lam, Patrick; Koch, Stephanie, Lactam-Containing Compounds And Derivatives Thereof As Factor Xa Inhibitors, Bristol-Myers Squibb Company, United States, EP1427415B1, August 12, 2009
- Delavenne, Xavier; Mismetti, Patrick; Basset, Thierry, Rapid determination of apixaban concentration in human plasma by liquid chromatography/tandem mass spectrometry: Application to pharmacokinetic study, Journal of Pharmaceutical and Biomedical Analysis, Volume: 78-79, Pages: 150-153, 2013
Frequently Asked Questions
Impurities in Apixaban can arise from various sources, such as contaminants in starting materials, reagents, or solvents used during manufacturing, degradation of the drug substance during storage or handling, and residual solvents or other impurities from the manufacturing process.
Impurity profiling is a critical step in Apixaban manufacturing as it helps identify, characterize, and quantify impurities present in the drug substance. It helps to optimize the manufacturing process and ensure the drug’s quality, safety, and efficacy.
Common impurities found in Apixaban include degradation products and residual solvents and may result from the manufacturing process, such as unreacted starting materials, reagents, or by-products.
Apixaban impurities are removed through purification steps such as recrystallization, distillation, or chromatography.
Apixaban impurities are stored at a controlled room temperature between 2-8 °C or as indicated on the Certificate of Analysis (CoA).
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