China (Mainland)
- Product Details
Keywords
- Rivaroxaban
- 366789-02-8
- C19H18ClN3O5S
Quick Details
- ProName: Rivaroxaban
- CasNo: 366789-02-8
- Molecular Formula: C19H18ClN3O5S
- Appearance: white powder
- Application: Animal Pharmaceuticals
- DeliveryTime: 2-3day
- PackAge: 25KG/Cardboard bucket or as required
- Port: shanghai or other
- ProductionCapacity: 5 Metric Ton/Month
- Purity: 99（%）
- Storage: cool and dry place
- Transportation: by sea or by air
- LimitNum: 1 Kilogram
Superiority
| Rivaroxaban Basic information |
| Product Name: | Rivaroxaban |
| Synonyms: | Rivaroxaban;5-Chloro-N-(((5S)-2-oxo-3-(4-(3-oxomorpholin-4-yl)phenyl)-1,3-oxazolidin-5-yl)methyl)thiophene-2-carboxamide;2-Thiophenecarboxamide, 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl];Xarelto;(S)-5-chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide;Rivaroxaban (BAY59-7939);BAY 59-7939 (Rivaroxaban);Rivarobaxan |
| CAS: | 366789-02-8 |
| MF: | C19H18ClN3O5S |
| MW: | 435.88 |
| EINECS: | 685-132-2 |
| Product Categories: | Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;API;-;Inhibitors;Inhibitor;Rivaroxaban;Pharmaceutical raw materials |
| Mol File: | 366789-02-8.mol |
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| Rivaroxaban Chemical Properties |
| Melting point | 228-229°C |
| storage temp. | Refrigerator |
| Safety Information |
| Rivaroxaban Usage And Synthesis |
| Description |
Rivaroxaban is a pure (S)-enantiomer. It is an odorless, non-hygroscopic, white to yellowish powder. Rivaroxaban is only slightly soluble in organic solvents (e.g., acetone, polyethylene glycol 400) and is practically insoluble in water and aqueous media. Rivaroxaban, a FXa inhibitor, is the active ingredient in XARELTO Tablets. XARELTO a kind of orally anticoagulant drug which is used for the prevention of blood clots. Rivaroxaban takes effect through competitively inhibiting free and clot bound factor Xa, which is needed to activate prothrombin (factor II) to thrombin (factor IIa). The later is a serine protease that is required to activate fibrinogen to fibrin, which is the loose meshwork that completes the clotting process. Each XARELTO tablet contains 10 mg, 15 mg, or 20 mg of rivaroxaban. The inactive ingredients of XARELTO are: croscarmellose sodium, hypromellose, lactose monohydrate, magnesium stearate, microcrystalline cellulose, and sodium lauryl sulfate. Additionally, the proprietary film coating mixture used for XARELTO 10 mg tablets is Opadry(R) Pink and for XARELTO 15 mg tablets is Opadry(R) Red, both containing ferric oxide red, hypromellose, polyethylene glycol 3350, and titanium dioxide, and for XARELTO 20 mg tablets is Opadry(R) II Dark Red, containing ferric oxide red, polyethylene glycol 3350, polyvinyl alcohol (partially hydrolyzed), talc, and titanium dioxide. |
| Indications and Usage |
Rivaroxaban is an antithrombotic drug and was developed in a collaboration between the German Bayer Pharmaceuticals and American Johnson company. It is different from the traditional antithrombotic drug heparin in that Rivaroxaban does not need the participation of antithrombin III and can directly antagonize free and bound Xa factors. Heparin requires the effects of antithrombin III, and has no effect on Xa factors in the prothrombin complex. Rivaroxaban is the first oral direct Xa factor inhibitor in the whole world, and it can selectively and competitively inhibit free and bound Da factors as well as prothrombin activity. It uses a dose-dependent method to extend the partial thromboplastin time (PTT) and activated partial thromboplastin time (aPTT) to extend clotting time and lower thrombin genesis. Rivaroxaban has the characteristics of high bioavailability, wide range of target diseases, stable dose-effect relationship, easy oral intake, and low bleeding risk. Rivaroxaban can also prevent and treat venous thrombosis. It is mainly used clinically to prevent deep venous thrombosis (DVT) and pulmonary embolism (PE) in adult patients following hip and knee replacement surgery. It is also used to prevent patients with nonvalvular atrial fibrillation from cerebral apoplexy and noncentral nervous system embolism, and it can lower the recurrence risk of coronary syndromes. |
| Mechanism of Action | Rivaroxaban is a selective inhibitor of FXa. It does not require a cofactor (such as Anti-thrombin III) for activity. Rivaroxaban inhibits free FXa and prothrombinase activity. Rivaroxaban has no direct effect on platelet aggregation, but indirectly inhibits platelet aggregation induced by thrombin. By inhibiting FXa, rivaroxaban decreases thrombin generation. |
| What is XARELTO？ |
XARELTO (Rivaroxaban) is a prescription medicine used to:
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| Uses |
Rivaroxaban is recommended as an option for treating pulmonary embolism and preventing recurrent deep vein thrombosis and pulmonary embolism in adults.
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| important information about XARELTO |
For people taking XARELTO for atrial fibrillation: People with atrial fibrillation (an irregular heart beat) are at an increased risk of forming a blood clot in the heart, which can travel to the brain, causing a stroke, or to other parts of the body. XARELTO lowers your chance of having a stroke by helping to prevent clots from forming. If you stop taking XARELTO, you may have increased risk of forming a clot in your blood. XARELTO can cause bleeding which can be serious, and rarely may lead to death. This is because XARELTO is a blood thinner medicine that reduces blood clotting. While you take XARELTO you are likely to bruise more easily and it may take longer for bleeding to stop. You may have a higher risk of bleeding if you take XARELTO and take other medicines that increase your risk of bleeding, including:
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| Carcinogenesis, Mutagenesis, Impairment of Fertility |
Rivaroxaban was not carcinogenic when administered by oral gavage to mice or rats for up to 2 years. The systemic exposures (AUCs) of unbound rivaroxaban in male and female mice at the highest dose tested (60 mg/kg/day) were 1- and 2-times, respectively, the human exposure of unbound drug at the human dose of 20 mg/day. Systemic exposures of unbound drug in male and female rats at the highest dose tested (60 mg/kg/day) were 2- and 4-times, respectively, the human exposure. Rivaroxaban was not mutagenic in bacteria (Ames-Test) or clastogenic in V79 Chinese hamster lung cells in vitro or in the mouse micronucleus test in vivo. No impairment of fertility was observed in male or female rats when given up to 200 mg/kg/day of rivaroxaban orally. This dose resulted in exposure levels, based on the unbound AUC, at least 13 times the exposure in humans given 20 mg rivaroxaban daily. |
| Adverse Reactions | Bleeding events (may be serious or fatal), back pain, wound secretion, pruritus, pain in extremity, abdominal pain, blister. |
| Description | Venous thromboembolism continues to be a major health concern despite conventional anticoagulation therapies. Rivaroxaban is a recent market introduction that directly inhibits FXa with high potency (Ki＝0.4 nM; IC50＝0.7 nM) and selectivity＞10,000-fold over other related serine proteases (thrombin, trypsin, plasmin, FVIIa, FIXa, FXIa, urokinase, and activated protein C). From the X-ray crystal structure, the central oxazolidinone moiety anchors the drug through two hydrogen bonds to Gly219 and directs the morpholinone group into the S4 pocket and the chlorothiophene portion into the S1 pocket. These key components may be coupled together synthetically by a couple of routes. 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. |
| Chemical Properties | White Solid |
| Originator | Bayer (Germany) |
| Uses | A novel antithrombotic agent. A highly potent and selective, direct FXa inhibitor |
| Uses | anti-coagulant; Factor X inhibitor，Rivaroxaban is an orally active, direct inhibitor of Factor Xa (Ki = 0.4 nM), which is a crucial component of the intrinsic and extrinsic pathways of the blood coagulation cascade.It demonstrates >10,000-fold greater selectivity for Factor Xa compared to other related serine proteases.In various animal arterial and venous thrombosis models, rivaroxaban is reported to inhibit thrombin formation without prolonging bleeding time and has been approved for clinical use as an anticoagulant in the prevention of stroke and the treatment of venous thromboembolisms. |
| Definition | ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-chlorothiophene-2-carboxylic acid with the amino group of 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. An anticoagulant u ed for prophylaxis of venous thromboembolism in patients with knee or hip replacement surgery. |
| Brand name | Xarelto |
| Side effects | Regarding safety, there was no statistical difference in the incidence of major postoperative bleeding between any of the rivaroxaban dose groups and enoxaparin although there did appear to be a dose dependency in the rivaroxaban set. In addition to bleeding and subsequent posthemorrhagic anemia, presenting as weakness, paleness, asthenia, dizziness, headache, or unexplained swelling, other common adverse events included nausea, increased GGT, and an increase in transglutaminase. Owing to its mechanism of action, there is a bleeding risk, so the drug is contraindicated in patients with clinically active bleeding. Rivaroxaban is also contraindicated in pregnant and breast-feeding women and in patients with hepatic disease associated with coagulopathy and clinically relevant bleeding risk. |
| Chemical Synthesis | Rivaroxaban is a recent market introduction that directly inhibits FXa with high potency (Ki 0.4 nM; IC50 0.7 nM) and selectivity, W10,000-fold over other related serine proteases (thrombin, trypsin, plasmin, FVIIa, FIXa, FXIa, urokinase, and activated protein C). From the X-ray crystal structure, the central oxazolidinone moiety anchors the drug through two hydrogen bonds to Gly219 and directs the morpholinone group into the S4 pocket and the chlorothiophene portion into the S1 pocket. These key components may be coupled together synthetically by a couple of routes. 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. The drug is formulated in 10-mg tablets for once-daily oral administration to patients undergoing elective hip or knee replacement surgery to prevent VTE. |
Details
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