Betrixaban | PRT054021 | CAS#330942-05-7 | factor Xa inhibitor

MedKoo Cat#: 319884 | Name: Betrixaban

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Betrixaban, also known as PRT054021, MK-4448; PRT-021; PRT-054021; MLN-1021, is a potent, orally active and highly selective factor Xa inhibitor undergone human clinical trials for prevention of embolism after knee surgery, and prevention of stroke following atrial fibrillation. Betrixaban is currently being studied in a human clinical trial for extended duration thromboprophylaxis to prevent venous thromboembolism in acute medically ill patients.

Chemical Structure

Betrixaban

CAS#330942-05-7 (free base)

Theoretical Analysis

MedKoo Cat#: 319884

Name: Betrixaban

CAS#: 330942-05-7 (free base)

Chemical Formula: C23H22ClN5O3

Exact Mass: 451.1411

Molecular Weight: 451.91

Elemental Analysis: C, 61.13; H, 4.91; Cl, 7.84; N, 15.50; O, 10.62

Price and Availability

Size	Price	Availability
5mg	USD 90.00	Ready to ship
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship

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Related CAS #

936539-80-9 (maleate) 330942-05-7 (free base)

Synonym

PRT054021; PRT 054021; PRT-054021; MK-4448; MK 4448; MK4448; PRT-021; PRT 021; PRT021; MLN-1021; MLN 1021; MLN1021; Betrixaban.

IUPAC/Chemical Name

N-(5-Chloropyridin-2-yl)-2-((4-(N,N-dimethylcarbamimidoyl)benzoyl)amino)-5- methoxybenzamide

InChi Key

XHOLNRLADUSQLD-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31)

SMILES Code

O=C(NC1=NC=C(Cl)C=C1)C2=CC(OC)=CC=C2NC(C3=CC=C(C(N(C)C)=N)C=C3)=O

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, not in water

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A8T02K14

QC Data

View QC data: current batch, Lot#A8T02K14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Betrixaban (PRT054021) is a factor Xa inhibitor with IC50 of 1.5 nM.

In vitro activity:

In order to determine which coagulation assay(s) should be used to assess the impact of betrixaban on haemostasis, betrixaban was spiked at final concentrations ranging from 0 to 250 ng/mL in platelet-poor plasma. Different reagents from several manufacturers were tested and the impact of betrixaban on pro-thrombin time (PT), activated partial thromboplastin time (aPTT), dilute Russel viper venom time (dRVV-T), chromogenic anti-Xa assays, thrombin generation assay (TGA), and a large panel of haemostasis diagnostic tests has been assessed. A concentration-dependent prolongation of aPTT, PT and dRVV-T was observed. The sensitivity mainly depended on the reagent. Chromogenic anti-Xa assays showed high sensitivity depending on the reagent. These assays applicable for other direct factor Xa inhibitors have to be adapted to obtain a relevant range of measurement. TGA may also be attractive to assess the anti-coagulant activity of betrixaban. Reference: Thromb Haemost. 2018 Jul;118(7):1203-1214. https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0038-1657772

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	20.7	45.74
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.44
	DMF	2.0	4.43

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 451.91 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.

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. Siriez R, Evrard J, Dogné JM, Pochet L, Gheldof D, Chatelain B, Mullier F, Douxfils J. Betrixaban: Impact on Routine and Specific Coagulation Assays-A Practical Laboratory Guide. Thromb Haemost. 2018 Jul;118(7):1203-1214. doi: 10.1055/s-0038-1657772. Epub 2018 Jun 11. PMID: 29890519.

In vitro protocol:

In vivo protocol:

TBD

1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Betrixaban. 2023 Feb 16. PMID: 31643763. 2: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Betrixaban. 2018 Dec 3. PMID: 29999975. 3: Murphy G, Grace Y, Chaudry S, Chamoun R. Betrixaban: A Novel Oral Anticoagulant With a New Niche. J Pharm Technol. 2018 Jun;34(3):123-133. doi: 10.1177/8755122518759765. Epub 2018 Feb 26. PMID: 34861030; PMCID: PMC6580730. 4: Thoenes M, Minguet J, Bramlage K, Bramlage P, Ferrero C. Betrixaban - the next direct factor Xa inhibitor? Expert Rev Hematol. 2016 Dec;9(12):1111-1117. doi: 10.1080/17474086.2016.1256194. Epub 2016 Nov 17. PMID: 27809616. 5: Lekura J, Kalus JS. Overview of betrixaban and its role in clinical practice. Am J Health Syst Pharm. 2018 Aug 1;75(15):1095-1102. doi: 10.2146/ajhp170785. Epub 2018 Jun 25. PMID: 29941506. 6: Miller KM, Brenner MJ. Betrixaban for Extended Venous Thromboembolism Prophylaxis in High-Risk Hospitalized Patients: Putting the APEX Results into Practice. Drugs. 2019 Feb;79(3):291-302. doi: 10.1007/s40265-019-1059-y. PMID: 30719631. 7: Nafee T, Gibson CM, Yee MK, Alkhalfan F, Chi G, Travis R, Mir M, Kalayci A, Jafarizade M, Ganti A, Kazmi SH, Ghaffarpasand E, Pitliya A, Datta S, Sharfaei S, Alihashemi M, Elsaiey A, Qamar I, Jahansouz M, Talib U, Kahe F, Habibi S, Abdelwahed M, Tariq F, Kaur M, Younes A, Walia SS, Singh A, Dildar SM, Afzal MK, Kerneis M. Betrixaban for first-line venous thromboembolism prevention in acute medically ill patients with risk factors for venous thromboembolism. Expert Rev Cardiovasc Ther. 2018 Nov;16(11):845-855. doi: 10.1080/14779072.2018.1534068. Epub 2018 Oct 15. PMID: 30296387. 8: Dobesh PP, Trevarrow BJ. Betrixaban: Safely Reducing Venous Thromboembolic Events with Extended Prophylaxis. Am J Med. 2019 Mar;132(3):307-311. doi: 10.1016/j.amjmed.2018.08.024. Epub 2018 Sep 7. PMID: 30201249. 9: Baker DE. Formulary Drug Review: Betrixaban. Hosp Pharm. 2018 Feb;53(1):29-37. doi: 10.1177/0018578717739397. Epub 2017 Nov 6. PMID: 29434384; PMCID: PMC5805016. 10: Sylvester KW, Connors JM. Betrixaban in the prevention of venous thromboembolism in medically ill patients. Future Cardiol. 2018 Nov;14(6):455-470. doi: 10.2217/fca-2018-0052. Epub 2018 Oct 24. PMID: 30353749. 11: Lee K, Cham S, Lam S. Betrixaban: A Novel Factor Xa Inhibitor for the Prevention of Venous Thromboembolism in Acutely Ill Medical Patients. Cardiol Rev. 2018 Nov/Dec;26(6):331-338. doi: 10.1097/CRD.0000000000000227. PMID: 30067518. 12: Escolar G, Díaz-Ricart M, Arellano-Rodrigo E. Betrixaban: a direct oral inhibitor of activated factor X for the prophylaxis of venous thromboembolism in patients hospitalized for acute medical illness. Drugs Today (Barc). 2017 Aug;53(8):423-434. doi: 10.1358/dot.2017.53.8.2681448. PMID: 29119147. 13: Scarpa D, Denas G, Babuin L, Pengo V. The benefit of betrixaban for the extended thromboprophylaxis in acutely ill medical patients. Expert Opin Pharmacother. 2019 Feb;20(3):261-268. doi: 10.1080/14656566.2018.1558209. Epub 2019 Jan 7. PMID: 30615495. 14: Jasemizad T, Bromberg L, Hatton TA, Padhye LP. Oxidation of betrixaban to yield N-nitrosodimethylamine by water disinfectants. Water Res. 2020 Nov 1;186:116309. doi: 10.1016/j.watres.2020.116309. Epub 2020 Aug 17. PMID: 32836149. 15: Palladino M, Merli G, Thomson L. Evaluation of the oral direct factor Xa inhibitor - betrixaban. Expert Opin Investig Drugs. 2013 Nov;22(11):1465-72. doi: 10.1517/13543784.2013.825605. Epub 2013 Aug 22. PMID: 23964817. 16: Raymond J, Imbert L, Cousin T, Duflot T, Varin R, Wils J, Lamoureux F. Pharmacogenetics of Direct Oral Anticoagulants: A Systematic Review. J Pers Med. 2021 Jan 11;11(1):37. doi: 10.3390/jpm11010037. PMID: 33440670; PMCID: PMC7826504. 17: Chan NC, Bhagirath V, Eikelboom JW. Profile of betrixaban and its potential in the prevention and treatment of venous thromboembolism. Vasc Health Risk Manag. 2015 Jun 26;11:343-51. doi: 10.2147/VHRM.S63060. PMID: 26170684; PMCID: PMC4489817. 18: Dunois C. Laboratory Monitoring of Direct Oral Anticoagulants (DOACs). Biomedicines. 2021 Apr 21;9(5):445. doi: 10.3390/biomedicines9050445. PMID: 33919121; PMCID: PMC8143174. 19: Hussar DA, Inman B. Betrixaban, sofosbuvir/velpatasvir/voxilaprevir, and glecaprevir/pibrentasvir. J Am Pharm Assoc (2003). 2017 Nov-Dec;57(6):750-754. doi: 10.1016/j.japh.2017.10.002. PMID: 29092766. 20: Huisman MV, Klok FA. Pharmacological properties of betrixaban. Eur Heart J Suppl. 2018 May;20(Suppl E):E12-E15. doi: 10.1093/eurheartj/suy016. Epub 2018 May 9. PMID: 29977164; PMCID: PMC6016700.