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MedKoo Cat#: 300310 | Name: Rivaroxaban
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rivaroxaban, also known as BAY 59-7939, is an oral anticoagulant invented and manufactured by Bayer; in a number of countries it is marketed as Xarelto. If approved by the United States FDA, it will be marketed by Ortho-McNeil Pharmaceutical. It is the first available orally active direct factor Xa inhibitor. Rivaroxaban is well absorbed from the gut and maximum inhibition of factor Xa occurs four hours after a dose. The effects lasts 8–12 hours, but factor Xa activity does not return to normal within 24 hours so once-daily dosing is possible.

Chemical Structure

Rivaroxaban
Rivaroxaban
CAS#366789-02-8

Theoretical Analysis

MedKoo Cat#: 300310

Name: Rivaroxaban

CAS#: 366789-02-8

Chemical Formula: C19H18ClN3O5S

Exact Mass: 435.0656

Molecular Weight: 435.88

Elemental Analysis: C, 52.35; H, 4.16; Cl, 8.13; N, 9.64; O, 18.35; S, 7.36

Price and Availability

Size Price Availability Quantity
100mg USD 110.00 Ready to ship
200mg USD 180.00 Ready to ship
500mg USD 385.00 Ready to ship
1g USD 550.00 Ready to ship
2g USD 950.00 Ready to ship
5g USD 1,950.00 Ready to ship
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Related CAS #
No Data
Synonym
BAY59-7939; BAY 59-7939; BAY-59-7939; Rivaroxaban; trade name: Xarelto.
IUPAC/Chemical Name
(S)-5-chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide
InChi Key
KGFYHTZWPPHNLQ-AWEZNQCLSA-N
InChi Code
InChI=1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10-23(19(26)28-14)13-3-1-12(2-4-13)22-7-8-27-11-17(22)24/h1-6,14H,7-11H2,(H,21,25)/t14-/m0/s1
SMILES Code
O=C(C1=CC=C(Cl)S1)NC[C@H]2CN(C3=CC=C(N4C(COCC4)=O)C=C3)C(O2)=O
Appearance
XXXX solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Rivaroxaban (BAY 59-7939) is a highly potent, selective and direct Factor Xa (FXa) inhibitor, achieving a strong gain in anti-FXa potency (IC50 0.7 nM; Ki 0.4 nM).
In vitro activity:
Rivaroxaban (BAY 59-7939) is an oral, direct Factor Xa (FXa) inhibitor in development for the prevention and treatment of arterial and venous thrombosis. Rivaroxaban competitively inhibits human FXa (Ki 0.4 nM) with >10 000-fold greater selectivity than for other serine proteases; it also inhibits prothrombinase activity (IC50 2.1 nM). Rivaroxaban inhibits endogenous FXa more potently in human and rabbit plasma (IC50 21 nM) than rat plasma (IC50 290 nM). It demonstrates anticoagulant effects in human plasma, doubling prothrombin time (PT) and activates partial thromboplastin time at 0.23 and 0.69 μM, respectively. Reference: J Thromb Haemost. 2005 Mar;3(3):514-21. https://doi.org/10.1111/j.1538-7836.2005.01166.x
In vivo activity:
In vivo, Rivaroxaban (BAY 59-7939) reduced venous thrombosis (fibrin-rich, platelet-poor thrombi) dose dependently (ED(50) 0.1 mg kg(-1) i.v.) in a rat venous stasis model. BAY 59-7939 reduced arterial (fibrin- and platelet-rich) thrombus formation in an arteriovenous (AV) shunt in rats (ED(50) 5.0 mg kg(-1) p.o.) and rabbits (ED(50) 0.6 mg kg(-1) p.o.). Slight inhibition of FXa (32% at ED(50)) reduced thrombus formation in the venous model; to affect arterial thrombosis in the rat and rabbit, stronger inhibition of FXa (74%, 92% at ED(50)) was required. Calculated plasma levels in rabbits at the ED(50) were 14-fold lower than in the rat AV shunt model, correlating with the 14-fold lower IC(50) of FXa inhibition in rabbit compared with rat plasma; this may suggest a correlation between FXa inhibition and antithrombotic activity. Bleeding times in rats and rabbits were not significantly affected at antithrombotic doses (3 mg kg(-1) p.o., AV shunt). Reference: J Thromb Haemost. 2005 Mar;3(3):514-21. https://doi.org/10.1111/j.1538-7836.2005.01166.x
Solvent mg/mL mM
Solubility
DMSO 50.0 114.71
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 435.88 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Perzborn E, Strassburger J, Wilmen A, Pohlmann J, Roehrig S, Schlemmer KH, Straub A. In vitro and in vivo studies of the novel antithrombotic agent BAY 59-7939--an oral, direct Factor Xa inhibitor. J Thromb Haemost. 2005 Mar;3(3):514-21. doi: 10.1111/j.1538-7836.2005.01166.x. PMID: 15748242. 2. Gnoth MJ, Buetehorn U, Muenster U, Schwarz T, Sandmann S. In vitro and in vivo P-glycoprotein transport characteristics of rivaroxaban. J Pharmacol Exp Ther. 2011 Jul;338(1):372-80. doi: 10.1124/jpet.111.180240. Epub 2011 Apr 22. PMID: 21515813.
In vivo protocol:
1. Perzborn E, Strassburger J, Wilmen A, Pohlmann J, Roehrig S, Schlemmer KH, Straub A. In vitro and in vivo studies of the novel antithrombotic agent BAY 59-7939--an oral, direct Factor Xa inhibitor. J Thromb Haemost. 2005 Mar;3(3):514-21. doi: 10.1111/j.1538-7836.2005.01166.x. PMID: 15748242. 2. Gnoth MJ, Buetehorn U, Muenster U, Schwarz T, Sandmann S. In vitro and in vivo P-glycoprotein transport characteristics of rivaroxaban. J Pharmacol Exp Ther. 2011 Jul;338(1):372-80. doi: 10.1124/jpet.111.180240. Epub 2011 Apr 22. PMID: 21515813.
1: Kvasnicka T, Malikova I, Zenahlikova Z, Kettnerova K, Brzezkova R, Zima T, Ulrych J, Briza J, Netuka I, Kvasnicka J. Rivaroxaban - Metabolism, Pharmacologic Properties and Drug Interactions. Curr Drug Metab. 2017;18(7):636-642. doi: 10.2174/1389200218666170518165443. PMID: 28524005. 2: Mueck W, Stampfuss J, Kubitza D, Becka M. Clinical pharmacokinetic and pharmacodynamic profile of rivaroxaban. Clin Pharmacokinet. 2014 Jan;53(1):1-16. doi: 10.1007/s40262-013-0100-7. PMID: 23999929; PMCID: PMC3889701. 3: Cohen AT, Bauersachs R. Rivaroxaban and the EINSTEIN clinical trial programme. Blood Coagul Fibrinolysis. 2019 Apr;30(3):85-95. doi: 10.1097/MBC.0000000000000800. PMID: 30920394; PMCID: PMC6504120. 4: Cohen O, Levy-Mendelovich S, Ageno W. Rivaroxaban for the treatment of venous thromboembolism in pediatric patients. Expert Rev Cardiovasc Ther. 2020 Nov;18(11):733-741. doi: 10.1080/14779072.2020.1823218. Epub 2020 Sep 24. PMID: 32935597. 5: Chan NC, Weitz JI. Rivaroxaban for prevention and treatment of venous thromboembolism. Future Cardiol. 2019 Mar;15(2):63-77. doi: 10.2217/fca-2018-0076. Epub 2019 Feb 19. PMID: 30779598. 6: Gao Y, Jin H. Rivaroxaban for treatment of livedoid vasculopathy: A systematic review. Dermatol Ther. 2021 Sep;34(5):e15051. doi: 10.1111/dth.15051. Epub 2021 Jul 18. PMID: 34197012. 7: Schneckmann R, Döring M, Gerfer S, Gorressen S, Heitmeier S, Helten C, Polzin A, Jung C, Kelm M, Fender AC, Flögel U, Grandoch M. Rivaroxaban attenuates neutrophil maturation in the bone marrow niche. Basic Res Cardiol. 2023 Aug 14;118(1):31. doi: 10.1007/s00395-023-01001-5. PMID: 37580509; PMCID: PMC10425524. 8: Špinar J, Špinarová L. Rivaroxaban u rizikových pacientů [Rivaroxaban in high-risk patients]. Vnitr Lek. 2017 Summer;63(6):424-430. Czech. PMID: 28840739. 9: Scott LJ. Rivaroxaban: A Review for Secondary CV Prevention in CAD and PAD. Drugs. 2020 Sep;80(14):1465-1475. doi: 10.1007/s40265-020-01397-7. PMID: 32910441. 10: Xu C, Meng J. Is rivaroxaban an all-rounder? Int J Cardiol. 2023 Jan 15;371:228. doi: 10.1016/j.ijcard.2022.09.038. Epub 2022 Sep 21. PMID: 36152684. 11: Spiezia L, Campello E, Tormene D, Simioni P. Venous Thromboembolism in Children: The Rivaroxaban Experience. Semin Thromb Hemost. 2024 Sep;50(6):866-872. doi: 10.1055/s-0043-1778106. Epub 2024 Jan 5. PMID: 38181816. 12: Sanmartín M, Bellmunt S, Cosín-Sales J, García-Moll X, Riera-Mestre A, Almendro-Delia M, Hernández JL, Lozano F, Mazón P, Suarez Fernández C. Role of rivaroxaban in the prevention of atherosclerotic events. Expert Rev Clin Pharmacol. 2019 Aug;12(8):771-780. doi: 10.1080/17512433.2019.1637732. Epub 2019 Jul 9. PMID: 31269825. 13: Saini AT, Schorn VJ, Lin FY. Tonsillectomy on rivaroxaban. Am J Otolaryngol. 2015 Mar-Apr;36(2):280-2. doi: 10.1016/j.amjoto.2014.10.013. Epub 2014 Oct 22. PMID: 25456169. 14: Antoniou S. Rivaroxaban for the treatment and prevention of thromboembolic disease. J Pharm Pharmacol. 2015 Aug;67(8):1119-32. doi: 10.1111/jphp.12387. Epub 2015 Jun 9. PMID: 26059702. 15: Barón-Esquivias G, Marín F, Sanmartín Fernandez M. Rivaroxaban in patients with atrial fibrillation: from ROCKET AF to everyday practice. Expert Rev Cardiovasc Ther. 2017 May;15(5):403-413. doi: 10.1080/14779072.2017.1309293. Epub 2017 Mar 28. PMID: 28319424. 16: Mardi P, Abbasi B, Shafiee A, Afsharmoghaddam T. Pharmacogenetic Approach for the Prevention of Rivaroxaban's ADRs: A Systematic Review and Meta-Analysis. Genet Res (Camb). 2023 Oct 31;2023:6105320. doi: 10.1155/2023/6105320. PMID: 37942082; PMCID: PMC10630013. 17: Camm AJ. The Rivaroxaban Program and the Management of Unmet Needs in Thromboembolic Disease. Thromb Haemost. 2018 May;118(S 01):S2-S11. doi: 10.1055/s-0038-1632387. Epub 2018 Mar 22. PMID: 29566415. 18: Zhang X, Cai Q, Wang X, Liao K, Hu C, Chen H. Current use of rivaroxaban in elderly patients with venous thromboembolism (VTE). J Thromb Thrombolysis. 2021 Oct;52(3):863-871. doi: 10.1007/s11239-021-02415-5. Epub 2021 Mar 5. PMID: 33674983. 19: Tsilimigras DI, Moris D, Karaolanis G, Kakkos SK, Filis K, Sigala F. Rivaroxaban versus Clopidogrel for Peripheral Artery Disease: A Clinico-Economic Approach of the COMPASS Trial. Curr Pharm Des. 2018;24(38):4516-4517. doi: 10.2174/1381612825666190101100832. PMID: 30621559. 20: Alqahtani S, Alnahdi J, Almofada R, Bin Hazza A, Alsultan A, Alqahtani F. Population Pharmacokinetics of Rivaroxaban in Real-World Patients. J Clin Pharmacol. 2023 Aug;63(8):943-949. doi: 10.1002/jcph.2255. Epub 2023 May 13. PMID: 37102317.