Rivaroxaban Basic information
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Product Name: |
Rivaroxaban |
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Synonyms: |
(S)-Rivaroxaban;(S)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)-oxazolidin-5-yl)methyl)thiophene-2-carbox;RIVAROXABAN STAGE-IV [5-CHLORO-N-({5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-1,3-OXAZOLIDIN-5-YL}-METHYL)-2(AS PER INV;5-Chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide;BAY 59-7939;Rivaroxaban Isomer;Rivaroxaban;5-Chloro-N-(((5S)-2-oxo-3-(4-(3-oxomorpholin-4-yl)phenyl)-1,3-oxazolidin-5-yl)methyl)thiophene-2-carboxamide |
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CAS: |
366789-02-8 |
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MF: |
C19H18ClN3O5S |
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MW: |
435.88 |
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EINECS: |
685-132-2 |
Rivaroxaban Chemical Properties
| Melting point | 228-229°C |
| Boiling point | 732.6±60.0 °C(Predicted) |
| density | 1.460±0.06 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | insoluble in H2O; insoluble in EtOH; ≥13.9 mg/mL in DMSO with gentle warming |
| form | solid |
| pka | 13.36±0.46(Predicted) |
Rivaroxaban Usage And Synthesis
| Chemical Properties | White Solid |
| Uses | Rivaroxaban is a novel antithrombotic agent. It is a novel, oral, selective direct inhibitor of factor Xa developed by Bayer Healthcare. It has been approved by the EMEA and FDA for the prevention ofvenous thromboembolism in adult patients after total hip replacement or total kneereplacement surgery. |
| Synthesis | To date, several methods have been reported for the synthesis of rivaroxaban. Most of them share the use of 5-S-hydroxymethyl or 5-S-aminomethyl oxazolidinones (2and 3 respectively) as key intermediates. Condensation of 3-morpholinone with 4-fluoronitrobenzene followed by catalytic hydrogenation provides N-(p-aminophenyl)morpholinone for subsequent reaction with (S)-2-(phthalimidomethyl)oxirane. With establishment of the aminoalcohol adduct, cyclization with 1,1′-carbonyldiimidazole generates the central oxazolidinone. Deprotection and acylation with 5-chlorothiophene-2-carbonyl chloride affords rivaroxaban. An Improved Synthesis of Rivaroxaban |
Rivaroxaban, trade name "Barital", produced by Bayer Healthcare, Germany, is an oral drug. To treat deep vein thrombosis and pulmonary embolism in adults to reduce the low recurrence risk of Chemicalbook. In addition, it can prevent venous thrombosis in adult patients undergoing elective hip or knee replacement surgery and use it in non-valvular atrial fibrillation, reducing the risk of stroke and systemic embolism.
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