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Rivaroxaban

Description Indications and Usage Mechanism of Action What is XARELTO? Uses important information about XARELTO Carcinogenesis, Mutagenesis, Impairment of Fertility Adverse Reactions
Rivaroxaban
Rivaroxaban structure
CAS No.
366789-02-8
Chemical Name:
Rivaroxaban
Synonyms
CS-273;Xarelto;Rivaroxaba;Rivaroxban;Rivaroxaban;Rivarobaxan;BAY 59-7939;Rivanoxaban;Rivaroxaban API;(S)-Rivaroxaban
CBNumber:
CB91176772
Molecular Formula:
C19H18ClN3O5S
Formula Weight:
435.88
MOL File:
366789-02-8.mol

Rivaroxaban Properties

Melting point:
228-229°C
Boiling point:
732.6±60.0 °C(Predicted)
Density 
1.460±0.06 g/cm3(Predicted)
storage temp. 
Refrigerator
pka
13.36±0.46(Predicted)
FDA UNII
9NDF7JZ4M3

Rivaroxaban price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 16043 Rivaroxaban ≥98% 366789-02-8 1mg $65 2020-06-24 Buy
Cayman Chemical 16043 Rivaroxaban ≥98% 366789-02-8 5mg $163 2020-06-24 Buy
Cayman Chemical 16043 Rivaroxaban ≥98% 366789-02-8 10mg $260 2020-06-24 Buy
Cayman Chemical 16043 Rivaroxaban ≥98% 366789-02-8 50mg $650 2020-06-24 Buy

Rivaroxaban Chemical Properties,Uses,Production

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.
XARELTO (Rivaroxaban) 20mg tablets
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:
  1. reduce the risk of stroke and blood clots in people who have a medical condition called atrial fibrillation. With atrial fibrillation, part of the heart does not beat the way it should. This can lead to the formation of blood clots, which can travel to the brain, causing a stroke, or to other parts of the body.
  2. treat blood clots in the veins of your legs (deep vein thrombosis) or lungs (pulmonary embolism) and reduce the risk of them occurring again
  3. reduce the risk of forming a blood clot in the legs and lungs of people who have just had hip or knee replacement surgery It is not known if XARELTO is safe and effective in children.
  4. It is not known if XARELTO is safe and effective in children.

Uses

Rivaroxaban is recommended as an option for treating pulmonary embolism and preventing recurrent deep vein thrombosis and pulmonary embolism in adults.
  1. Rivaroxaban (Xarelto, Bayer) is indicated for the 'treatment of deep vein thrombosis and pulmonary embolism, and prevention of recurrent deep vein thrombosis and pulmonary embolism in adults'. For the initial treatment of acute pulmonary embolism, the recommended dosage of rivaroxaban is 15 mg twice daily for the first 21 days followed by 20 mg once daily for continued treatment and prevention of recurrent venous thromboembolism.
  2. Non-Valvular Atrial Fibrillation (NVAF)* to prevent stroke & systemic embolism.
  3. Acute VTE treatment & prevention of recurrent VTE [for deep vein thrombosis (DVT) and pulmonary embolism (PE)].
  4. Prevention of venous thromboembolic events (VTE) in elective total hip or knee replacement surgery (THR, TKR).

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:
  1. aspirin or aspirin containing products
  2. non-steroidal anti-inflammatory drugs (NSAIDs)
  3. warfarin sodium (Coumadin®, Jantoven®)
  4. any medicine that contains heparin
  5. clopidogrel (Plavix®)
  6. selective serotonin reuptake inhibitors (SSRIs) or serotonin norepinephrine reuptake inhibitors (SNRIs)
  7. other medicines to prevent or treat blood clots
Tell your doctor if you take any of these medicines. Ask your doctor or pharmacist if you are not sure if your medicine is one listed above.

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.

Rivaroxaban Preparation Products And Raw materials

Raw materials

Preparation Products


Rivaroxaban Suppliers

Global( 429)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Nanjing Gold Pharmaceutical Technology Co. Ltd.
025-84209270 15906146951
025-84209270 wgp@nanjing-pharmaceutical.com CHINA 115 55
Jiangsu Zhongbang Pharmaceutical Co., Ltd.
025-87151996
025-87151996 zbsales@chinaredsun.com CHINA 32 55
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Casorganics US Corp
+17326109938
sales@casorganics.com CHINA 175 58
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 497 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22626 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile
+86-571-56059825 fandachem@gmail.com CHINA 3252 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3014 60
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 739 60
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 24723 60

View Lastest Price from Rivaroxaban manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-07-05 Rivaroxaban
366789-02-8
US $10.00 / KG 1KG 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
2020-07-10 Rivaroxaban
366789-02-8
1ASSAYS 99%min 20Ton Hebei Xibaijie Biotechnology Co., Ltd.
2018-08-21 Rivaroxaban
366789-02-8
US $7.00 / KG 1KG 99% 1000KG career henan chemical co

366789-02-8(Rivaroxaban)Related Search:


  • CS-273
  • 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)
  • Rivarobaxan
  • Rivaroxaban(Xarelto)
  • Rivaroxaba
  • (S)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)-oxazolidin-5-yl)methyl)thiophene-2-carboxami
  • Rivaroxaban API
  • Rivaroxban
  • Rivaroxaban, >=99%
  • BAY 59-7939 (Rivaroxaban)
  • (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
  • Rivaroxaban Isomer
  • 5-Chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide
  • BAY 59-7939
  • 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl]thioph
  • Rivaroxaban intermediates
  • Rivanoxaban
  • (S)-5-chloro-N-{[2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl} thiophene-2-carboxamide
  • 366789-02-8
  • 151596-47-0
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  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
  • API
  • Inhibitor
  • Rivaroxaban
  • Pharmaceutical raw materials
  • Inhibitors
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