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Systematic (IUPAC) name
Clinical data
Trade names Eliquis
Licence data EMA:Link
Legal status
Routes Oral
Pharmacokinetic data
Bioavailability ca. 50%
Half-life 9–14 h
Excretion 75% biliary, 25% renally
CAS number 503612-47-3 YesY
ATC code B01A
PubChem CID 10182969
DrugBank DB07828
ChemSpider 8358471 YesY
KEGG D03213 YesY
Chemical data
Formula C25H25N5O4 
Molecular mass 459.497 g/mol
 YesY (what is this?)  (verify)

Apixaban (BMS-562247-01, tradename Eliquis) is an anticoagulant for the treatment of venous thromboembolic events. It is a direct factor Xa inhibitor. Apixaban has been available in Europe since May 2012.[1] In the United States, it is undergoing phase III trials for the prevention of venous thromboembolism.[2] An FDA decision on apixaban which was expected on June 28, 2012 was delayed.[3][4] On August 21, 2014, Pfizer announced that Apixaban was now FDA approved for treatment and secondary prophylaxis of DVT and PE.[5] It is being developed in a joint venture by Pfizer and Bristol-Myers Squibb.[6][7]

Medical uses[edit]

Apixaban is indicated for the following:[8]

Atrial Fibrillation[edit]

Apixaban is recommended by the National Institute for Health and Clinical Excellence for the prevention of stroke and systemic embolism in people with non-valvular atrial fibrillation and at least one of the following risk factors: prior stroke or transient ischemic attack, age 75 years or older, diabetes, or symptomatic heart failure. This recommendation was based on the results of a single 18,201 person Phase 3 trial comparing people treated with apixaban to people treated with warfarin and having an international normalized ratio ((NR) target range of 2.0 to 3.0. In this trial, apixaban was associated with a reduced risk of stroke and systemic embolism compared to warfarin over a period of 1.8 years (hazard ratio 0.79). The risk of fatal or disabling stroke was also reduced in the apixaban treatment arm (hazard ratio 0.71). Apixaban was associated with fewer total deaths than warfarin, though the difference was only marginally statistically significant (HR 0.89, p=0.047).The average person in the warfarin arm of the trial remained within the targeted INR range was 62%, which the institute concluded was typical of people on warfarin therapy in the United Kingdom.[9]

Side effects[edit]

Premature discontinuation of any oral anticoagulant, including apixaban, increases thrombotic event risk for reasons other than pathological bleeding or completion of therapy course. To reduce this risk, administering another anticoagulant is advised.[10]


Apixaban can increase the risk of bleeding and may even cause serious, potentially fatal, bleeding. Concurrent use with drugs affecting hemostasis (e.g. other anticoagulants, heparin, aspirin and other antiplatelet drugs, selective serotonin reuptake inhibitors, serotonin norepinephrine reuptake inhibitors, and nonsteroidal anti-inflammatory drugs (NSAIDs) can further increase the risk of bleeding.[8]

Spinal puncture[edit]

When spinal/epidural anesthesia or puncture is utilized, patients who are being treated with anti-thrombotic agents for the prevention of thromboembolic complications are at risk for developing a hematoma, which can cause long-term or permanent paralysis. The risk of this may be increased by using epidural or intrathecal catheters after a surgical operation or from the concurrent use of medicinal agents that affect hemostasis.[8]

Mechanism of action[edit]

Apixaban is a highly selective, orally bioavailable, and reversible direct inhibitor of free and clot-bound factor Xa. Factor Xa catalyzes the conversion of prothrombin to thrombin, the final enzyme in the coagulation cascade that is responsible for fibrin clot formation.[11] Apixaban has no direct effect on platelet aggregation, but by inhibiting factor Xa, it indirectly decreases platelet formation induced by thrombin.[8]

Clinical trials[edit]

A 2007 trial showed that apixaban was equivalent to enoxaparin/open-label heparin in preventing thrombosis in patients who had undergone a knee replacement.[12] A 2010 trial showed that apixaban was superior to enoxaparin in preventing thrombosis in patients undergoing elective hip replacement surgery, with similar bleeding rates.[13][14]

A 2011 trial showed that in patients with atrial fibrillation who have failed or are not candidates for vitamin K antagonist therapy, apixaban, as compared with aspirin, reduced the risk of stroke or systemic embolism in patients experiencing atrial fibrillation by more than 50% (from 3.7% per year with aspirin to 1.6% per year with Apixaban). Difference in death rates did not reach statistical significance.[15] A 2011 trial showed that patients receiving apixaban after acute coronary syndrome experienced an increased rate of major bleeding episodes without a significant reduction in recurrent ischemic events.[16] For this reason, the trial was terminated early. In a head-to-head study (Phase 3 ARISTOTLE trial[17]) of apixaban versus warfarin,[18] apixaban met both its primary endpoint (“noninferiority” to warfarin in preventing strokes) and a key secondary endpoint (superior compared to warfarin in avoiding major bleeding).[19]

See also[edit]


  1. ^ "ELIQUIS® (apixaban) Approved In Europe For Preventing Venous Thromboembolism After Elective Hip Or Knee Replacement" (Press release). Pfizer. April 20, 2012. Retrieved 2012-05-29. 
  2. ^ Turpie AG (June 2007). "Oral, direct factor Xa inhibitors in development for the prevention and treatment of thromboembolic diseases". Arterioscler. Thromb. Vasc. Biol. 27 (6): 1238–47. doi:10.1161/ATVBAHA.107.139402. PMID 17379841. 
  3. ^ Huston, Larry (February 29, 2012). "Decision on Apixaban (Eliquis) Pushed Back By Three Months". Forbes. Retrieved 2012-05-29. 
  4. ^ Husten, Larry. "FDA Once Again Delays Approval Of Apixaban (Eliquis)". Forbes. Retrieved 17 July 2012. 
  5. ^ http://www.pfizer.com/news/press-release/press-release-detail/u_s_fda_approves_eliquis_apixaban_for_the_treatment_of_deep_vein_thrombosis_dvt_and_pulmonary_embolism_pe_and_for_the_reduction_in_the_risk_of_recurrent_dvt_and_pe_following_initial_therapy
  6. ^ "Bristol-Myers Squibb News Release 26 April 2007". Archived from the original on 11 September 2007. Retrieved 2007-09-15. 
  7. ^ Nainggolan, Lisa. "Apixaban better than European enoxaparin regimen for preventing VTE". Retrieved 2011-04-01. 
  8. ^ a b c d "Eliquis (apixaban) [prescribing information]". Princeton, NJ: Bristol-Myers Squibb. March 2014. Retrieved 2014-10-29. 
  9. ^ "www.nice.org.uk". 
  10. ^ "ELIQUIS® (apixaban) tablets Factor Xa Inhibitor". FDA. August 2014. Retrieved 2014-11-02. 
  11. ^ Frost C, Wang J, Nepal S, et al. (February 2013). "Apixaban, an oral, direct factor Xa inhibitor: single dose safety, pharmacokinetics, pharmacodynamics and food effect in healthy subjects". Br J Clin Pharmacol 75 (2): 476–87. doi:10.1111/j.1365-2125.2012.04369.x. PMID 22759198. 
  12. ^ Lassen MR, Davidson BL, Gallus A, Pineo G, Ansell J, Deitchman D (2007). "The efficacy and safety of apixaban, an oral, direct factor Xa inhibitor, as thromboprophylaxis in patients following total knee replacement". J. Thromb. Haemost. 5 (12): 2368–75. doi:10.1111/j.1538-7836.2007.02764.x. PMID 17868430. 
  13. ^ Lassen MR, Gallus A, Raskob GE, Pineo G, Chen D, Ramirez LM, ADVANCE-3 Investigators (December 2010). "Apixaban versus enoxaparin for thromboprophylaxis after hip replacement". N. Engl. J. Med. 363 (26): 2487–98. doi:10.1056/NEJMoa1006885. PMID 21175312. 
  14. ^ Nainggolan L. "Apixaban better than European enoxaparin regimen for preventing VTE". theheart.org by WebMD. Retrieved 2011-04-01. 
  15. ^ "Apixaban in patients with atrial fibrillation". N. Engl. J. Med. 364 (9): 806–817. March 2011. doi:10.1056/NEJMoa1007432. PMID 21309657.  edit
  16. ^ Alexander JH, Lopes RD, James S, et al. (August 2011). "Apixaban with antiplatelet therapy after acute coronary syndrome". N. Engl. J. Med. 365 (8): 699–708. doi:10.1056/NEJMoa1105819. PMID 21780946. 
  17. ^ "Apixaban for the Prevention of Stroke in Subjects With Atrial Fibrillation (ARISTOTLE)". NCT00412984. ClinicalTrials.gov. Retrieved 2011-06-23. 
  18. ^ Granger CB, Alexander JH, McMurray JJV, et al. (August 2011). "Apixaban versus Warfarin in Patients with Atrial Fibrillation". New England Journal of Medicine 365. doi:10.1056/NEJMoa1107039. 
  19. ^ Husten L (2011-06-22). "ELIQUIS® (apixaban) Meets Primary and Key Secondary Endpoints in Phase 3 ARISTOTLE Study". CardioBrief. WordPress.com. Retrieved 2011-06-23.