Apixaban

• CAT Number: A000903
• CAS Number: 503612-47-3
• Molecular Formula: C25H25N5O4
• Molecular Weight: 459.5
• Purity: ≥95%
• Target: Thrombin
• Solubility: >11.5mg/mL in DMSO
• Storage: -20°C
• IUPAC Name: 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxamide
• 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)
• InChIKey: QNZCBYKSOIHPEH-UHFFFAOYSA-N
• SMILES: COC1=CC=C(C=C1)N2C3=C(CCN(C3=O)C4=CC=C(C=C4)N5CCCCC5=O)C(=N2)C(=O)N

Apixaban(CAS 503612-47-3), sold under the tradename Eliquis, is an anticoagulant for the treatment of venous thromboembolic events. It is taken by mouth. It is a direct factor Xa inhibitor.Apixaban is indicated for the following: (1) To lower the risk of stroke and embolism in patients with nonvalvular atrial fibrillation. (2) Deep vein thrombosis (DVT) prophylaxis. DVT/'s may lead to pulmonary embolism (PE) in knee or hip replacement surgery patients. (3) Treatment of both DVT and PE. (4) To reduce the risk of recurring DVT and PE after initial therapy.

 

Overview of Clinical Research

Apixaban is factor Xa inhibitor. The phase III study of Apixaban on acute coronary syndromes is ongoing. 

Reference

1: Evanger N, Szkotak A, Stang L, Bungard TJ. Apixaban Concentration with and without Coadministration of Carbamazepine: A Case with No Apparent Interaction. Can J Hosp Pharm. 2017 Nov-Dec;70(6):463-467. Epub 2017 Dec 21. PubMed PMID: 29299007; PubMed Central PMCID: PMC5737190.
2: Siegal D, Lu G, Leeds JM, Karbarz M, Castillo J, Mathur V, Hutchaleelaha A, Sinha U, Kitt M, McClure M, Hollenbach SJ, Curnutte JT, Conley PB, Crowther M. Safety, pharmacokinetics, and reversal of apixaban anticoagulation with andexanet alfa. Blood Adv. 2017 Sep 22;1(21):1827-1838. doi: 10.1182/bloodadvances.2017007112. eCollection 2017 Sep 26. PubMed PMID: 29296829; PubMed Central PMCID: PMC5728098.
3: Koretsune Y, Ikeda T, Kozuma K, Hirano T, Yasaka M, Kida M, Chachin M, Imura M. Patient satisfaction after switching from warfarin to apixaban in patients with nonvalvular atrial fibrillation: AGAIN study. Patient Prefer Adherence. 2017 Dec 15;11:1987-1996. doi: 10.2147/PPA.S152579. eCollection 2017. PubMed PMID: 29290682; PubMed Central PMCID: PMC5735985.
4: Brodsky SV, Mhaskar NS, Thiruveedi S, Dhingra R, Reuben SC, Calomeni E, Ivanov I, Satoskar A, Hemminger J, Nadasdy G, Hebert L, Rovin B, Nadasdy T. Acute kidney injury aggravated by treatment initiation with apixaban: Another twist of anticoagulant-related nephropathy. Kidney Res Clin Pract. 2017 Dec;36(4):387-392. doi: 10.23876/j.krcp.2017.36.4.387. Epub 2017 Dec 31. PubMed PMID: 29285431; PubMed Central PMCID: PMC5743048.
5: Faust AC, Tran DM, Lo C, Lai S, Sheperd L, Liu M, Denetclaw T. Managing Nonoperable Intracranial Bleeding Associated With Apixaban: A Series of 2 Cases. J Pharm Pract. 2017 Jan 1:897190017697884. doi: 10.1177/0897190017697884. [Epub ahead of print] PubMed PMID: 29278991.
6: Berry A, Brancheau D, Zughaib M. Rapid resolution of left ventricular thrombus with apixaban therapy. SAGE Open Med Case Rep. 2017 Dec 11;5:2050313X17745211. doi: 10.1177/2050313X17745211. eCollection 2017. PubMed PMID: 29276599; PubMed Central PMCID: PMC5734448.
7: Bryk AH, Łukaszuk R, Donicz P, Plens K, Undas A. Efficacy and safety of apixaban in real‑life patients at high bleeding risk. Pol Arch Intern Med. 2017 Dec 22;127(12):889-891. doi: 10.20452/pamw.4169. Epub 2017 Dec 15. PubMed PMID: 29272262.
8: Krumme AA, Pawar A, Schneeweiss S, Glynn RJ, Choudhry NK, Kulldorff M, Ortiz AS, Avorn J, Gagne JJ. Study protocol for the dabigatran, apixaban, rivaroxaban, edoxaban, warfarin comparative effectiveness research study. J Comp Eff Res. 2017 Dec 21. doi: 10.2217/cer-2017-0053. [Epub ahead of print] PubMed PMID: 29264930.
9: Santangelo G, Ielasi A, Antonio Scopelliti P, Pattarino F, Tespili M. Apixaban-Induced Resolution of A Massive Left Atrial and Appendage Thrombosis in a Very Elderly Patient. J Atr Fibrillation. 2016 Dec 31;9(4):1509. doi: 10.4022/jafib.1509. eCollection 2016 Dec. PubMed PMID: 29250263; PubMed Central PMCID: PMC5673322.
10: Janczak DT, Mimier MK, McBane RD, Kamath PS, Simmons BS, Bott-Kitslaar DM, Lenz CJ, Vargas ER, Hodge DO, Wysokinski WE. Rivaroxaban and Apixaban for Initial Treatment of Acute Venous Thromboembolism of Atypical Location. Mayo Clin Proc. 2018 Jan;93(1):40-47. doi: 10.1016/j.mayocp.2017.10.007. Epub 2017 Dec 6. PubMed PMID: 29217335.