Apixaban
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MedKoo CAT#: 300170

CAS#: 503612-47-3

Description: Apixaban, also known as BMS-56224701, is an anticoagulant for the treatment of venous thromboembolic events. Apixaban is a direct factor Xa inhibitor. Apixaban was approved in 2012. 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.

Chemical Structure

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Apixaban
CAS# 503612-47-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 300170
Name: Apixaban
CAS#: 503612-47-3
Chemical Formula: C25H25N5O4
Exact Mass: 459.19
Molecular Weight: 459.500
Elemental Analysis: C, 65.35; H, 5.48; N, 15.24; O, 13.93

Price and Availability

Size Price Availability Quantity
50mg USD 90 Ready to ship
100mg USD 125 Ready to ship
500mg USD 250 Ready to ship
1g USD 350 Ready to ship
2g USD 550 Ready to ship
5g USD 950 Ready to ship
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Synonym: BMS56224701; BMS 56224701; BMS-56224701; Apixaban, brand name: Eliquis

IUPAC/Chemical Name: 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[5,4-c]pyridine-3-carboxamide

InChi Key: QNZCBYKSOIHPEH-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(C1=NN(C2=CC=C(OC)C=C2)C3=C1CCN(C4=CC=C(N5C(CCCC5)=O)C=C4)C3=O)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Apixaban (BMS 562247-01) is an inhibitor of Factor Xa with Ki of 0.08 nM and 0.17 nM in human and rabbit, respectively.
In vitro activity: Macro (HUVEC) and microvascular (HMEC) endothelial cells (ECs) were exposed to serum from uremic patients or healthy donors, in absence and presence of apixaban (60 ng/ml). Changes in surface VCAM-1 and ICAM-1, intracellular eNOS, reactive oxygen species (ROS), and von Willebrand Factor (VWF) production by immunofluorescence, reactivity of the extracellular matrix (ECM) towards platelets, and intracellular signaling were evaluated. ECs exposed to uremic serum triggered dysregulation of all the parameters. Presence of apixaban resulted in decreased expression of VCAM-1 (178 ± 14 to 89 ± 2% on HMEC and 324 ± 71 to 142 ± 25% on HUVEC) and ICAM-1 (388 ± 60 to 111 ± 10% on HMEC and 148 ± 9% to 90 ± 7% on HUVEC); increased eNOS (72 ± 8% to 95 ± 10% on HMEC); normalization of ROS levels (173 ± 21 to 114 ± 13% on HMEC and 165 ± 14 to 127 ± 7% on HUVEC); lower production of VWF (168 ± 14 to 92 ± 4% on HMEC and 151 ± 22 to 99 ± 11% on HUVEC); and decreased platelet adhesion onto ECM (134 ± 22 to 93 ± 23% on HMEC and 161 ± 14 to 117 ± 7% on HUVEC). Apixaban inhibited p38MAPK and p42/44 activation in HUVEC (139 ± 15 to 48 ± 15% and 411 ± 66 to 177 ± 57%, respectively) (p < 0.05 vs control for all parameters). Anti-FXa strategies, such as apixaban, prevented ED caused by the uremic milieu, exhibiting anti-inflammatory and antioxidant properties and modulating the reactivity of the ECM. Reference: Cardiovasc Drugs Ther. 2021 Jun;35(3):521-532. https://link.springer.com/article/10.1007%2Fs10557-020-07010-z
In vivo activity: As an inhibitor of FXa (prothrombin), Apixaban inhibits prothrombin conversion into thrombin leading to thrombin deficiency in vivo. Myocardial fibrosis-bearing mice induced by continuous myocardial ischemia (MI) had higher levels of thrombin. Orally administration of apixaban significantly abrogated fibrosis condition and thrombin levels. Thrombin induced collagen deposition by activation of the Par-1-coupled Gq/PKC signaling. Genetic ablation of Gq or pharmacological inhibition of PKC effectively blunted thrombin-induced collagen deposition in cardiac fibroblasts. Moreover, administration of PKC inhibitor or Gq antagonist obviously blocked MI-induced myocardial fibrosis in mice. To conclude, apixaban attenuates MI-induced myocardial fibrosis by inhibition of thrombin-dependent Par-1/Gq/PKC signaling axis. Reference: Biochem Biophys Res Commun. 2018 Jun 7;500(3):550-556. https://www.sciencedirect.com/science/article/abs/pii/S0006291X18308404?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 3.0 6.53
DMSO 34.0 73.99
DMSO:PBS (pH 7.2) (1:1) 0.5 1.09

Preparing Stock Solutions

The following data is based on the product molecular weight 459.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Guasti L, Squizzato A, Moretto P, Vigetti D, Ageno W, Dentali F, Maresca AM, Campiotti L, Grandi AM, Passi A. In vitro effects of Apixaban on 5 different cancer cell lines. PLoS One. 2017 Oct 12;12(10):e0185035. doi: 10.1371/journal.pone.0185035. PMID: 29023465; PMCID: PMC5638249. 2. Torramade-Moix S, Palomo M, Vera M, Jerez D, Moreno-Castaño AB, Zafar MU, Rovira J, Diekmann F, Garcia-Pagan JC, Escolar G, Cases A, Diaz-Ricart M. Apixaban Downregulates Endothelial Inflammatory and Prothrombotic Phenotype in an In Vitro Model of Endothelial Dysfunction in Uremia. Cardiovasc Drugs Ther. 2021 Jun;35(3):521-532. doi: 10.1007/s10557-020-07010-z. PMID: 32651897. 3. Shi G, Yang X, Pan M, Sun J, Ke H, Zhang C, Geng H. Apixaban attenuates ischemia-induced myocardial fibrosis by inhibition of Gq/PKC signaling. Biochem Biophys Res Commun. 2018 Jun 7;500(3):550-556. doi: 10.1016/j.bbrc.2018.04.071. Epub 2018 Apr 24. PMID: 29654769. 4. Bushi D, Chapman J, Wohl A, Stein ES, Feingold E, Tanne D. Apixaban decreases brain thrombin activity in a male mouse model of acute ischemic stroke. J Neurosci Res. 2018 Aug;96(8):1406-1411. doi: 10.1002/jnr.24253. Epub 2018 May 14. PMID: 29761540.
In vitro protocol: 1. Guasti L, Squizzato A, Moretto P, Vigetti D, Ageno W, Dentali F, Maresca AM, Campiotti L, Grandi AM, Passi A. In vitro effects of Apixaban on 5 different cancer cell lines. PLoS One. 2017 Oct 12;12(10):e0185035. doi: 10.1371/journal.pone.0185035. PMID: 29023465; PMCID: PMC5638249. 2. Torramade-Moix S, Palomo M, Vera M, Jerez D, Moreno-Castaño AB, Zafar MU, Rovira J, Diekmann F, Garcia-Pagan JC, Escolar G, Cases A, Diaz-Ricart M. Apixaban Downregulates Endothelial Inflammatory and Prothrombotic Phenotype in an In Vitro Model of Endothelial Dysfunction in Uremia. Cardiovasc Drugs Ther. 2021 Jun;35(3):521-532. doi: 10.1007/s10557-020-07010-z. PMID: 32651897.
In vivo protocol: 1. Shi G, Yang X, Pan M, Sun J, Ke H, Zhang C, Geng H. Apixaban attenuates ischemia-induced myocardial fibrosis by inhibition of Gq/PKC signaling. Biochem Biophys Res Commun. 2018 Jun 7;500(3):550-556. doi: 10.1016/j.bbrc.2018.04.071. Epub 2018 Apr 24. PMID: 29654769. 2. Bushi D, Chapman J, Wohl A, Stein ES, Feingold E, Tanne D. Apixaban decreases brain thrombin activity in a male mouse model of acute ischemic stroke. J Neurosci Res. 2018 Aug;96(8):1406-1411. doi: 10.1002/jnr.24253. Epub 2018 May 14. PMID: 29761540.

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1: Touma L, Filion KB, Atallah R, Eberg M, Eisenberg MJ. A meta-analysis of randomized controlled trials of the risk of bleeding with apixaban versus vitamin K antagonists. Am J Cardiol. 2015 Feb 15;115(4):533-41. doi: 10.1016/j.amjcard.2014.11.039. Epub 2014 Dec 2. Review. PubMed PMID: 25547937.

2: Zalpour A, Oo TH. Clinical utility of apixaban in the prevention and treatment of venous thromboembolism: current evidence. Drug Des Devel Ther. 2014 Nov 5;8:2181-91. doi: 10.2147/DDDT.S51006. eCollection 2014. Review. PubMed PMID: 25395835; PubMed Central PMCID: PMC4226443.

3: Hanna MS, Mohan P, Knabb R, Gupta E, Frost C, Lawrence JH. Development of apixaban: a novel anticoagulant for prevention of stroke in patients with atrial fibrillation. Ann N Y Acad Sci. 2014 Nov;1329:93-106. doi: 10.1111/nyas.12567. Epub 2014 Nov 5. Review. PubMed PMID: 25377080; PubMed Central PMCID: PMC4260137.

4: Moorman ML, Nash JE, Stabi KL. Emergency surgery and trauma in patients treated with the new oral anticoagulants: dabigatran, rivaroxaban, and apixaban. J Trauma Acute Care Surg. 2014 Sep;77(3):486-94; quiz 486-94. doi: 10.1097/TA.0000000000000360. Review. PubMed PMID: 25159255.

5: Alotaibi G, Alsaleh K, Wu C, Mcmurtry MS. Dabigatran, rivaroxaban and apixaban for extended venous thromboembolism treatment: network meta-analysis. Int Angiol. 2014 Aug;33(4):301-8. Review. PubMed PMID: 25056161.

6: Kakkos SK, Kirkilesis GI, Tsolakis IA. Editor's Choice - efficacy and safety of the new oral anticoagulants dabigatran, rivaroxaban, apixaban, and edoxaban in the treatment and secondary prevention of venous thromboembolism: a systematic review and meta-analysis of phase III trials. Eur J Vasc Endovasc Surg. 2014 Nov;48(5):565-75. doi: 10.1016/j.ejvs.2014.05.001. Epub 2014 Jun 18. Review. PubMed PMID: 24951377.

7: Apixaban and atrial fibrillation: no clear advantage. Prescrire Int. 2014 Feb;23(146):33-6. Review. PubMed PMID: 24669381.

8: Meddahi S, Samama MM. [Pharmacologic and clinical characteristics of direct inhibitors of factor Xa: rivaroxaban, apixaban, edoxaban and betrixaban]. J Mal Vasc. 2014 May;39(3):183-94. doi: 10.1016/j.jmv.2014.02.001. Epub 2014 Mar 18. Review. French. PubMed PMID: 24650612.

9: Bhanwra S, Ahluwalia K. The new factor Xa inhibitor: Apixaban. J Pharmacol Pharmacother. 2014 Jan;5(1):12-4. doi: 10.4103/0976-500X.124409. Review. PubMed PMID: 24554904; PubMed Central PMCID: PMC3917159.

10: Gómez-Outes A, Terleira-Fernández AI, Calvo-Rojas G, Suárez-Gea ML, Vargas-Castrillón E. Dabigatran, Rivaroxaban, or Apixaban versus Warfarin in Patients with Nonvalvular Atrial Fibrillation: A Systematic Review and Meta-Analysis of Subgroups. Thrombosis. 2013;2013:640723. doi: 10.1155/2013/640723. Epub 2013 Dec 22. Review. PubMed PMID: 24455237; PubMed Central PMCID: PMC3885278.

11: {blacktriangledown} Apixaban and {blacktriangledown} rivaroxaban for stroke prevention in AF. Drug Ther Bull. 2014 Jan;52(1):6-9. doi: 10.1136/dtb.2014.1.0228. Epub 2014 Jan 8. Review. PubMed PMID: 24401533.

12: Imai N, Fujii Y, Amano M. [Pharmacological properties and clinical efficacy of apixaban (Eliquis(®)]. Nihon Yakurigaku Zasshi. 2013 Nov;142(5):247-54. Review. Japanese. PubMed PMID: 24212595.

13: Amin A, Deitelzweig S, Jing Y, Makenbaeva D, Wiederkehr D, Lin J, Graham J. Comparison of Medical Costs of Patients With Atrial Fibrillation Unsuitable for Warfarin Treatment With Apixaban or Aspirin Based on AVERROES Trial. Clin Appl Thromb Hemost. 2015 Apr;21(3):235-40. doi: 10.1177/1076029613507335. Epub 2013 Oct 9. Review. PubMed PMID: 24108232.

14: Hess CN, Al-Khatib SM, Granger CB, Lopes R. A review of apixaban for stroke prevention in atrial fibrillation: insights from ARISTOTLE. Expert Rev Cardiovasc Ther. 2013 Sep;11(9):1105-14. doi: 10.1586/14779072.2013.824181. Epub 2013 Sep 2. Review. PubMed PMID: 23992517.

15: Pujadas-Mestres L, Escolar G, Arellano-Rodrigo E, Galán AM. Apixaban in the prevention of stroke and systemic embolism in nonvalvular atrial fibrillation. Drugs Today (Barc). 2013 Jul;49(7):425-36. doi: 10.1358/dot.2013.49.7.1980498. Review. PubMed PMID: 23914351.

16: Aguilar MI, Kuo RS, Freeman WD. New anticoagulants (dabigatran, apixaban, rivaroxaban) for stroke prevention in atrial fibrillation. Neurol Clin. 2013 Aug;31(3):659-75. doi: 10.1016/j.ncl.2013.03.001. Review. PubMed PMID: 23896498.

17: Bleeding with dabigatran, rivaroxaban, apixaban. No antidote, and little clinical experience. Prescrire Int. 2013 Jun;22(139):155-9. Review. PubMed PMID: 23866358.

18: Fawole A, Daw HA, Crowther MA. Practical management of bleeding due to the anticoagulants dabigatran, rivaroxaban, and apixaban. Cleve Clin J Med. 2013 Jul;80(7):443-51. doi: 10.3949/ccjm.80a.13025. Review. PubMed PMID: 23821689.

19: Gong IY, Kim RB. Importance of pharmacokinetic profile and variability as determinants of dose and response to dabigatran, rivaroxaban, and apixaban. Can J Cardiol. 2013 Jul;29(7 Suppl):S24-33. doi: 10.1016/j.cjca.2013.04.002. Review. PubMed PMID: 23790595.

20: Keating GM. Apixaban: a review of its use for reducing the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation. Drugs. 2013 Jun;73(8):825-43. doi: 10.1007/s40265-013-0063-x. Review. PubMed PMID: 23677804.