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Apixaban information


Apixaban
Clinical data
Trade namesEliquis, others
Other namesBMS-562247-01
AHFS/Drugs.comMonograph
MedlinePlusa613032
License data
  • US DailyMed: Apixaban
Pregnancy
category
  • AU: C[1]
Routes of
administration
By mouth
ATC code
  • B01AF02 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)[3]
  • US: WARNING[2]Rx-only[4]
  • EU: Rx-only[5]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability~50%
Protein binding~87%
MetabolismCYP3A4, CYP3A5, CYP1A2 and others
Elimination half-life9–14 h
ExcretionBile duct (75%), kidney (25%)
Identifiers
IUPAC name
  • 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide
CAS Number
  • 503612-47-3 checkY
PubChem CID
  • 10182969
IUPHAR/BPS
  • 6390
DrugBank
  • DB07828 checkY
ChemSpider
  • 8358471 checkY
UNII
  • 3Z9Y7UWC1J
KEGG
  • D03213 checkY
ChEMBL
  • ChEMBL231779 checkY
CompTox Dashboard (EPA)
  • DTXSID80436500 Edit this at Wikidata
ECHA InfoCard100.167.332 Edit this at Wikidata
Chemical and physical data
FormulaC25H25N5O4
Molar mass459.506 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C5N(c4ccc(N3C(=O)c1c(c(nn1c2ccc(OC)cc2)C(=O)N)CC3)cc4)CCCC5
InChI
  • InChI=1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32) checkY
  • Key:QNZCBYKSOIHPEH-UHFFFAOYSA-N checkY
  (verify)

Apixaban, sold under the brand name Eliquis, is an anticoagulant medication used to treat and prevent blood clots and to prevent stroke in people with nonvalvular atrial fibrillation through directly inhibiting factor Xa.[6][7][8] Specifically, it is used to prevent blood clots following hip or knee replacement and in those with a history of prior clots.[6][8] It is used as an alternative to warfarin and does not require monitoring by blood tests[6] or dietary restrictions.[9] It is taken by mouth.[6]

Common side effects include bleeding and nausea.[6][7] Other side effects may include bleeding around the spine and allergic reactions.[6] Use is not recommended during pregnancy or breastfeeding.[1][7] Use appears to be relatively safe in those with mild kidney problems.[7] Compared to warfarin it has fewer interactions with other medications.[10] It is a direct factor Xa inhibitor.[6]

In 2007, Pfizer and Bristol-Myers Squibb began development of apixaban as an anticoagulant.[11] Apixaban was approved for medical use in the European Union in May 2011, and in the United States in December 2012.[5][6][12] It is on the World Health Organization's List of Essential Medicines.[13] In 2021, it was the 33rd most commonly prescribed medication in the United States with more than 17 million prescriptions.[14][15] It is available as a generic medication, although not in the United States.[8][16]

  1. ^ a b "Apixaban (Eliquis) Use During Pregnancy". Drugs.com. 21 June 2019. Retrieved 13 August 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "Eliquis 5 mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 3 May 2022. Retrieved 8 October 2022.
  4. ^ Cite error: The named reference Eliquis FDA label was invoked but never defined (see the help page).
  5. ^ a b "Eliquis EPAR". European Medicines Agency. 17 September 2018. Retrieved 22 April 2020. Text was copied from this source which is © European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  6. ^ a b c d e f g h "Apixaban Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 27 March 2019.
  7. ^ a b c d British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 124–125. ISBN 9780857113382.
  8. ^ a b c "FDA approves first generics of Eliquis". U.S. Food and Drug Administration (FDA). 23 December 2019. Archived from the original on 23 December 2019. Retrieved 23 December 2019. Public Domain This article incorporates text from this source, which is in the public domain.
  9. ^ Hall H (September–October 2020). "How a Drug Is Born". Skeptical Inquirer. Amherst, New York: Center for Inquiry.
  10. ^ Kiser K (2017). Oral Anticoagulation Therapy: Cases and Clinical Correlation. Springer. p. 11. ISBN 9783319546438.
  11. ^ "Bristol-Myers Squibb and Pfizer Announce Worldwide Collaboration to Develop and Commercialize Anticoagulant and Metabolic Compounds". Pfizer (Press release). Archived from the original on 10 September 2015. Retrieved 25 December 2021.
  12. ^ "Drug Approval Package: Eliquis (apixaban) NDA #202155". U.S. Food and Drug Administration (FDA). 13 February 2013. Retrieved 23 December 2019.
  13. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  14. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  15. ^ "Apixaban - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  16. ^ "With Court Win, BMS and Pfizer Stave Off Generic Challengers to Eliquis – For Now". BioSpace. Retrieved 29 November 2021.

and 28 Related for: Apixaban information

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Apixaban

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Apixaban, sold under the brand name Eliquis, is an anticoagulant medication used to treat and prevent blood clots and to prevent stroke in people with...

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Andexanet alfa

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Andexxa among others, is an antidote for the medications rivaroxaban and apixaban, when reversal of anticoagulation is needed due to uncontrolled bleeding...

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Relative risk

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risk factors. For example, in a study examining the effect of the drug apixaban on the occurrence of thromboembolism, 8.8% of placebo-treated patients...

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Anticoagulant

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population and minor bleeding in 167 more people per 1000 population. Apixaban had no effect on mortality, recurrence of blood clots in blood vessels...

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Dabigatran

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anticoagulants for patients with atrial fibrillation. Results demonstrated apixaban use was associated with lower risk for gastrointestinal bleeding and similar...

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Adverse drug reaction

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metabolized by CYP3A4 such as the anticoagulant apixaban, which results in elevated blood concentrations of apixaban and greater risk of serious bleeds. Additionally...

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Thrombus

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Treatment Anticoagulants: edoxaban, tinzaparin, unfractionated heparin Medication apixaban, edoxaban, and rivaroxaban Deaths 100,000–300,000 each year...

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Ciraparantag

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(anti-blood clotting) drugs, including factor Xa inhibitors (rivaroxaban, apixaban and edoxaban), dabigatran, and heparins (including fondaparinux, low molecular...

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WHO Model List of Essential Medicines

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glycol-epoetin beta; and their quality-assured biosimilars are alternatives Apixaban, edoxaban, and rivaroxaban are alternatives Alternatives are dalteparin...

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Pulmonary embolism

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antagonists by American professional guidelines. Two of these (rivaroxaban and apixaban) do not require initial heparin or fondaparinux treatment, whereas dabigatran...

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Alexion Pharmaceuticals

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threatening or uncontrollable bleeding in people who are taking rivaroxaban or apixaban. With costs that can reach as much as $2 million per year, the drugs manufactured...

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Transient ischemic attack

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anticoagulant used, but direct acting oral anticoagulants (DOACs), such as apixaban, have been shown to be equally effective while also conferring a lower...

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Coagulation

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factors (the directly acting oral anticoagulants: dabigatran, rivaroxaban, apixaban, and edoxaban). Theories on the coagulation of blood have existed since...

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Atrial flutter

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rhythm is necessary. Long-term use of blood thinners (e.g., warfarin or apixaban) is an important component of treatment to reduce the risk of blood clot...

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Bristol Myers Squibb

Last Update:

Avapro (irbesartan) – comarketed with Sanofi Coumadin (warfarin) Eliquis (apixaban) – comarketed with Pfizer Plavix (clopidogrel) – comarketed with Sanofi...

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Vitamin K

Last Update:

greater than 10 but there is no active bleeding. The newer anticoagulants apixaban, dabigatran and rivaroxaban are not vitamin K antagonists. Coumarin is...

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Bayer

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competes with other newer generation anticoagulants such as edoxaban, apixaban, and dabigatran as well as with the generic anticoagulant warfarin. It...

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Pfizer

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are the Pfizer–BioNTech COVID-19 vaccine ($11 billion in 2023 revenues), apixaban ($6 billion in 2023 revenues), a pneumococcal conjugate vaccine ($6 billion...

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Edoxaban

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edoxaban overdose, but has only been approved for reversing rivaroxaban and apixaban effects by the FDA and the EMA as of 2019. Edoxaban is a direct, selective...

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Deep vein thrombosis

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thinners is the standard treatment. Typical medications include rivaroxaban, apixaban, and warfarin. Beginning warfarin treatment requires an additional non-oral...

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Corvalol

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medications that may have decreased effectiveness when used with Corvalol are apixaban, rivaroxaban, clozapine, itraconazole, nifedipine, biologics, and many...

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Drug nomenclature

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-barb- Barbiturates phenobarbital, secobarbital -xaban Direct Xa inhibitor apixaban, rivaroxaban -afil Inhibitor of PDE5 with vasodilator action sildenafil...

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Atrial fibrillation

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means including warfarin, heparin, dabigatran, rivaroxaban, edoxaban, and apixaban. Many issues should be considered related to their comparative effectiveness...

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Rivaroxaban

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Suárez-Gea ML, Vargas-Castrillón E (2013). "Dabigatran, Rivaroxaban, or Apixaban versus Warfarin in Patients with Nonvalvular Atrial Fibrillation: A Systematic...

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Stroke

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depending on the type of treatment used. Oral anticoagulants, especially Xa (apixaban) and thrombin (dabigatran) inhibitors have been shown to be superior to...

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Direct factor Xa inhibitors

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atrial fibrillation (AF). Direct factor Xa inhibitors include rivaroxaban, apixaban and edoxaban, and are types of direct oral anticoagulant (DOAC), which...

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Activated carbon

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extracting the direct oral anticoagulants (DOACs) such as dabigatran, apixaban, rivaroxaban and edoxaban from blood plasma samples. For this purpose it...

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Warfarin

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efficacy of warfarin without a need for monitoring, such as dabigatran, apixaban, edoxaban, and rivaroxaban, have been approved in a number of countries...

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