Rivaroxaban

• CAT Number: A000458
• CAS Number: 366789-02-8
• Molecular Formula: C₁₉H₁₈ClN₃O₅S
• Molecular Weight: 435.88
• Purity: ≥95%
• Synonyms: 366789-02-8; Xarelto; BAY 59-7939; (S)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide; UNII-9NDF7JZ4M3
• Target: Factor Xa
• Solubility: Soluble in DMSO > 10 mM
• Storage: -20°C
• InChI: 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
• InChIKey: KGFYHTZWPPHNLQ-AWEZNQCLSA-N
• SMILES: C1COCC(=O)N1C2=CC=C(C=C2)N3CC(OC3=O)CNC(=O)C4=CC=C(S4)Cl

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.

Reference

1: Cheung YW, Barco S, Mathôt RAA, van den Dool EJ, Stroobants AK, Serlie MJ,
Middeldorp S, Coppens M. Pharmacokinetics of dabigatran etexilate and rivaroxaban
in patients with short bowel syndrome requiring parenteral nutrition: The PDER
PAN study. Thromb Res. 2017 Nov 4;160:76-82. doi: 10.1016/j.thromres.2017.10.025.
[Epub ahead of print] PubMed PMID: 29127863.

2: Coleman CI, Weeda ER, Nguyen E, Bunz TJ, Sood NA. Effectiveness and Safety of
Rivaroxaban Versus Warfarin in Patients 80+ Years-of-Age with Nonvalvular Atrial
Fibrillation. Eur Heart J Qual Care Clin Outcomes. 2017 Nov 7. doi:
10.1093/ehjqcco/qcx044. [Epub ahead of print] PubMed PMID: 29121212.

3: Licata A, Puccia F, Lombardo V, Serruto A, Minissale MG, Morreale I,
Giannitrapani L, Soresi M, Montalto G, Almasio PL. Rivaroxaban-induced
hepatotoxicity: review of the literature and report of new cases. Eur J
Gastroenterol Hepatol. 2017 Nov 8. doi: 10.1097/MEG.0000000000001030. [Epub ahead
of print] PubMed PMID: 29120909.

4: Zhu J, Gao RJ, Liu Q, Jiang RH, Yu L, Sun YX, Zhang P, Lin JW, Ye Y, Zhang ZW,
Chen SQ, Cheng H, Sheng X, Jiang CY. Metabolic benefits of rivaroxaban in
non-valvular atrial fibrillation patients after radiofrequency catheter ablation.
J Zhejiang Univ Sci B. 2017 Nov.;18(11):946-954. doi: 10.1631/jzus.B1600492.
PubMed PMID: 29119732.

5: Levy JH, Moore KT, Neal MD, Schneider D, Marcsisin VS, Ariyawansa J, Weitz JI.
Rivaroxaban reversal with prothrombin complex concentrate or tranexamic acid in
healthy volunteers. J Thromb Haemost. 2017 Nov 6. doi: 10.1111/jth.13894. [Epub
ahead of print] PubMed PMID: 29106076.

6: Ciampa A, Salapete C, Vivolo S, Ames PRJ. Oral anticoagulation cost in primary
antiphospholipid syndrome: comparison between warfarin and hypothetical
rivaroxaban. Blood Coagul Fibrinolysis. 2017 Nov 1. doi:
10.1097/MBC.0000000000000682. [Epub ahead of print] PubMed PMID: 29095760.

7: Lyon C, Mathern S, Devitt J, DeSanto K. Rivaroxaban vs. Warfarin for Treatment
of DVT and PE. Am Fam Physician. 2017 Oct 15;96(8):532-533. PubMed PMID:
29094900.

8: Rivaroxaban plus aspirin for secondary prevention. Drug Ther Bull. 2017
Nov;55(11):124. doi: 10.1136/dtb.2017.10.0547. Epub 2017 Oct 31. PubMed PMID:
29089299.

9: Di Benedetto P, Zangari A, De Franceschi D, Di Benedetto ED, Cainero V,
Beltrame A, Gisonni R, Causero A. Rivaroxaban and early periprostethic joint
infection: our experience. Acta Biomed. 2017 Oct 18;88(4 -S):38-42. doi:
10.23750/abm.v88i4 -S.6792. PubMed PMID: 29083351.

10: Ismail R, Zaghrini E, Hitti E. Spontaneous Spinal Epidural Hematoma in a
Patient on Rivaroxaban: Case Report and Literature Review. J Emerg Med. 2017
Oct;53(4):536-539. doi: 10.1016/j.jemermed.2017.06.005. PubMed PMID: 29079069.