Misplaced Pages

This is an old revision of this page, as edited by Beetstra (talk | contribs) at 11:22, 8 August 2011 (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Apixaban

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	US: WARNING
Pharmacokinetic data
Bioavailability	ca. 50%
Elimination half-life	9–14 h
Excretion	75% biliary, 25% renally
Identifiers
IUPAC name 1-(4-methoxyphenyl)-7-oxo-6--4,5- dihydropyrazolopyridine- 3-carboxamide
CAS Number	503612-47-3
PubChem CID	10182969
DrugBank	DB07828
ChemSpider	8358471
UNII	3Z9Y7UWC1J
KEGG	D03213
ChEMBL	ChEMBL231779
CompTox Dashboard (EPA)	DTXSID80436500
ECHA InfoCard	100.167.332
Chemical and physical data
Formula	C25H25N5O4
Molar mass	459.497 g/mol g·mol
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) Key:QNZCBYKSOIHPEH-UHFFFAOYSA-N
(verify)

Apixaban (manufacturer's designation BMS-562247-01) is a compound being investigated as an anticoagulant. It is a direct factor Xa inhibitor. It is presently undergoing phase III trials in the prevention of venous thromboembolism, together with a number of related competing compounds, such as rivaroxaban. It is being developed in a joint venture by Pfizer and Bristol-Myers Squibb.

Clinical trials

A 2007 trial showed that apixaban was equivalent to enoxaparin/open-label heparin in preventing thrombosis in patients who had undergone a knee replacement.

A 2010 trial showed that apixaban was superior to enoxaparin in preventing thrombosis in patients undergoing elective hip replacement surgery, with similar bleeding rates.

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 fibrilation 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.

A 2011 trial showed that patients receiving Apixaban after acute coronary syndrome suffered an increase rate of major bleeding episodes without a significant reduction in recurrent ischemic events. For this reason, the trial was terminated early.

In a head to head study of apixaban versus warfarin, apixaban meet both its primary endpoint (“noninferiority” to warfarin in preventing strokes) and a key secondary endpoint (superior compared to warfarin in avoiding major bleeding).

References

1. "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 Oct 2023.
2. Turpie AG (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. "Bristol-Myers Squibb News Release 26 April 2007". Retrieved 2007-09-15.
4. Nainggolan, Lisa. "Apixaban better than European enoxaparin regimen for preventing VTE". Retrieved 1 April 2011.
5. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
6. Lassen MR, Gallus A, Raskob GE, Pineo G, Chen D, Ramirez LM, ADVANCE-3 Investigators (2010). "Apixaban versus enoxaparin for thromboprophylaxis after hip replacement". N. Eng. J. Med. 363 (26): 2487–98. doi:10.1056/NEJMoa1006885. PMID 21175312.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
7. Nainggolan, Lisa. "Apixaban better than European enoxaparin regimen for preventing VTE". http://www.theheart.org. Retrieved 1 April 2011. {{cite web}}: External link in |publisher= (help)
8. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1056/NEJMoa1007432, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1056/NEJMoa1007432 instead.
9. Alexander, J.; et al. (2011). "Apixaban with Antiplatelet Therapy after Acute Coronary Syndrome". New England Journal of Medicine. doi:10.1056/NEJMoa1105819. {{cite journal}}: Explicit use of et al. in: |author= (help)
10. "Apixaban for the Prevention of Stroke in Subjects With Atrial Fibrillation (ARISTOTLE)". NCT00412984. ClinicalTrials.gov. Retrieved 2011-06-23.
11. 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.

This drug article relating to the blood and blood forming organs is a stub. You can help Misplaced Pages by expanding it.

• v
• t
• e

• Drugs not assigned an ATC code
• Blood and blood forming organ drug stubs
• Anticoagulants
• Bristol-Myers Squibb
• Pyrazolopyridines
• Lactams
• Piperidines
• Phenol ethers