MedKoo Cat#: 300310 Name: Rivaroxaban CAS#: 366789-02-8 Chemical Formula: C19H18ClN3O5S Exact Mass: 435.06557 Molecular Weight: 435.88 Elemental Analysis: C, 52.35; H, 4.16; Cl, 8.13; N, 9.64; O, 18.35; S, 7.36

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

Technical Data

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).

Harmonized System Code: 293490

References

  1: Anticoagulation Monitoring and Reversal Strategies for Dabigatran, Rivaroxaban, and Apixaban: A Review of Clinical Effectiveness [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2012 Apr. Available from http://www.ncbi.nlm.nih.gov/books/NBK356439/ PubMed PMID: 27123509.

2: Uprichard J. Management of rivaroxaban in relation to bodyweight and body mass index. Ther Adv Cardiovasc Dis. 2016 Apr 17. pii: 1753944716643645. [Epub ahead of print] Review. PubMed PMID: 27090286.

3: Rivaroxaban (Xarelto): Treatment of Venous Thromboembolic Events (Deep Vein Thrombosis [DVT], Pulmonary Embolism [PE]) and Prevention of Recurrent DVT and PE [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK344331/ PubMed PMID: 26913324.

4: Vamos M, Cappato R, Marchlinski FE, Natale A, Hohnloser SH. Efficacy and safety of rivaroxaban compared with vitamin K antagonists for peri-procedural anticoagulation in catheter ablation of atrial fibrillation: a systematic review and meta-analysis. Europace. 2016 Jan 20. pii: euv408. [Epub ahead of print] Review. PubMed PMID: 26797248.

5: Cohen AT, Hamilton M, Mitchell SA, Phatak H, Liu X, Bird A, Tushabe D, Batson S. Comparison of the Novel Oral Anticoagulants Apixaban, Dabigatran, Edoxaban, and Rivaroxaban in the Initial and Long-Term Treatment and Prevention of Venous Thromboembolism: Systematic Review and Network Meta-Analysis. PLoS One. 2015 Dec 30;10(12):e0144856. doi: 10.1371/journal.pone.0144856. eCollection 2015. Review. PubMed PMID: 26716830; PubMed Central PMCID: PMC4696796.

6: Pandor A, Pollard D, Chico T, Henderson R, Stevenson M. Rivaroxaban for Preventing Atherothrombotic Events in People with Acute Coronary Syndrome and Elevated Cardiac Biomarkers: An Evidence Review Group Perspective of a NICE Single Technology Appraisal. Pharmacoeconomics. 2016 May;34(5):463-77. doi: 10.1007/s40273-015-0351-2. Review. PubMed PMID: 26689783.

7: Hirmanov VN. [New Anticoagulants in the Treatment of Patients With Recent Acute Coronary Syndrome. Place of Rivaroxaban]. Kardiologiia. 2015;55(6):98-104. Review. Russian. PubMed PMID: 26625526.

8: Morgan C, Body R. Best evidence topic reports. BET 1: is long-term Rivaroxaban superior to Warfarin in pulmonary embolism? Emerg Med J. 2015 Nov;32(11):895-8. doi: 10.1136/emermed-2015-205330.1. Review. PubMed PMID: 26490283.

9: Escolar G, Carne X, Arellano-Rodrigo E. Dosing of rivaroxaban by indication: getting the right dose for the patient. Expert Opin Drug Metab Toxicol. 2015;11(10):1665-77. doi: 10.1517/17425255.2015.1085022. Epub 2015 Sep 2. Review. PubMed PMID: 26329812.

10: Stöllberger C, Bastovansky A, Finsterer J. Fatal intracerebral bleeding under rivaroxaban. Int J Cardiol. 2015 Dec 15;201:110-2. doi: 10.1016/j.ijcard.2015.06.081. Epub 2015 Jun 26. Review. PubMed PMID: 26296048.

11: Spencer RJ, Amerena JV. Rivaroxaban in the Prevention of Stroke and Systemic Embolism in Patients with Non-Valvular Atrial Fibrillation: Clinical Implications of the ROCKET AF Trial and Its Subanalyses. Am J Cardiovasc Drugs. 2015 Dec;15(6):395-401. doi: 10.1007/s40256-015-0127-2. Review. PubMed PMID: 26062914.

12: 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. Review. PubMed PMID: 26059702.

13: Kwong L, Turpie AG. Real-world data confirm clinical trial outcomes for rivaroxaban in orthopaedic patients. Curr Orthop Pract. 2015 May;26(3):299-305. Review. PubMed PMID: 25973138; PubMed Central PMCID: PMC4420150.

14: Barón-Esquivias G, Fernández-Avilés F, Atienza F, Pastor Pueyo P, Toro R, Sanmartín Fernández M. Efficacy and safety of rivaroxaban in real-life patients with atrial fibrillation. Expert Rev Cardiovasc Ther. 2015 Apr;13(4):341-53. doi: 10.1586/14779072.2015.1026259. Review. PubMed PMID: 25797900.

15: Harder S. Pharmacokinetic and pharmacodynamic evaluation of rivaroxaban: considerations for the treatment of venous thromboembolism. Thromb J. 2014 Oct 28;12:22. doi: 10.1186/1477-9560-12-22. eCollection 2014. Review. PubMed PMID: 25698904; PubMed Central PMCID: PMC4334601.

16: Imberti D, Ambrosoli A, Cimminiello C, Compagnone C, Fanelli A, Tripodi A, Ottani F. Periprocedural management of rivaroxaban-treated patients. Expert Opin Pharmacother. 2015 Apr;16(5):685-91. doi: 10.1517/14656566.2015.1013939. Epub 2015 Feb 17. Review. PubMed PMID: 25690076.

17: Stöllberger C, Finsterer J. Relevance of P-glycoprotein in stroke prevention with dabigatran, rivaroxaban, and apixaban. Herz. 2015 Apr;40 Suppl 2:140-5. doi: 10.1007/s00059-014-4188-9. Epub 2015 Jan 25. Review. PubMed PMID: 25616425.

18: Arcelus JI, Domènech P, Fernández-Capitan Mdel C, Guijarro R, Jiménez D, Jiménez S, Lozano FS, Monreal M, Nieto JA, Páramo JA. Rivaroxaban in the treatment of venous thromboembolism and the prevention of recurrences: a practical approach. Clin Appl Thromb Hemost. 2015 May;21(4):297-308. doi: 10.1177/1076029614561321. Epub 2014 Dec 9. Review. PubMed PMID: 25504999.

19: 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. Review. PubMed PMID: 25456169.

20: Mitchell AP, Conway SE. Rivaroxaban for treatment of venous thromboembolism in older adults. Consult Pharm. 2014 Sep;29(9):627-30. doi: 10.4140/TCP.n.2014.627. Review. PubMed PMID: 25203412.