MedKoo Cat#: 126589 | Name: Razaxaban

Description:

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

Razaxaban (also known as BMS-561389 or DPC 906) is an oral factor Xa inhibitor that was being developed for the treatment of thrombosis.

Chemical Structure

Razaxaban
Razaxaban
CAS#218298-21-6 (free base)

Theoretical Analysis

MedKoo Cat#: 126589

Name: Razaxaban

CAS#: 218298-21-6 (free base)

Chemical Formula: C24H20F4N8O2

Exact Mass: 528.1645

Molecular Weight: 528.47

Elemental Analysis: C, 54.55; H, 3.81; F, 14.38; N, 21.20; O, 6.05

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Razaxaban; BMS-561389; DPC 906
IUPAC/Chemical Name
1-(3-aminobenzo[d]isoxazol-5-yl)-N-(4-(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-2-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide
InChi Key
OFJRNBWSFXEHSA-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H20F4N8O2/c1-34(2)12-21-30-7-8-35(21)13-3-5-17(16(25)10-13)31-23(37)18-11-20(24(26,27)28)32-36(18)14-4-6-19-15(9-14)22(29)33-38-19/h3-11H,12H2,1-2H3,(H2,29,33)(H,31,37)
SMILES Code
CN(C)CC1=NC=CN1C2=CC=C(NC(=O)C3=CC(=NN3C4=CC5=C(ON=C5N)C=C4)C(F)(F)F)C(F)=C2
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 528.47 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
1: Badawy SI, Narang AS, LaMarche K, Subramanian G, Varia SA. Mechanistic basis for the effects of process parameters on quality attributes in high shear wet granulation. Int J Pharm. 2012 Dec 15;439(1-2):324-33. doi: 10.1016/j.ijpharm.2012.09.011. PubMed PMID: 22981985. 2: Barrett YC, Wang Z, Knabb RM. A novel prothrombin time assay for assessing the anticoagulant activity of oral factor Xa inhibitors. Clin Appl Thromb Hemost. 2013 Sep;19(5):522-8. doi: 10.1177/1076029612441859. PubMed PMID: 22473028. 3: Pugh N, Jarvis GE, Koch A, Sakariassen KS, Davis B, Farndale RW. The impact of factor Xa inhibition on axial dependent arterial thrombus formation triggered by a tissue factor rich surface. J Thromb Thrombolysis. 2012 Jan;33(1):6-15. doi: 10.1007/s11239-011-0658-6. PubMed PMID: 22120925. 4: Barrett YC, Wang Z, Frost C, Shenker A. Clinical laboratory measurement of direct factor Xa inhibitors: anti-Xa assay is preferable to prothrombin time assay. Thromb Haemost. 2010 Dec;104(6):1263-71. doi: 10.1160/TH10-05-0328. PubMed PMID: 20978714. 5: Quan ML, Pinto DJ, Rossi KA, Sheriff S, Alexander RS, Amparo E, Kish K, Knabb RM, Luettgen JM, Morin P, Smallwood A, Woerner FJ, Wexler RR. Phenyltriazolinones as potent factor Xa inhibitors. Bioorg Med Chem Lett. 2010 Feb 15;20(4):1373-7. doi: 10.1016/j.bmcl.2010.01.011. PubMed PMID: 20100660. 6: Bátorová A. [Advances in antithrombotic treatment--antithrombotics with anti-Xa effect]. Vnitr Lek. 2009 Mar;55(3):295-301. Review. Slovak. PubMed PMID: 19378862. 7: Hilden LR, Pommier CJ, Badawy SI, Friedman EM. NIR chemical imaging to guide/support BMS-561389 tablet formulation development. Int J Pharm. 2008 Apr 2;353(1-2):283-90. doi: 10.1016/j.ijpharm.2007.11.032. PubMed PMID: 18182257. 8: Varnes JG, Wacker DA, Pinto DJ, Orwat MJ, Theroff JP, Wells B, Galemo RA, Luettgen JM, Knabb RM, Bai S, He K, Lam PY, Wexler RR. Structure-activity relationship and pharmacokinetic profile of 5-ketopyrazole factor Xa inhibitors. Bioorg Med Chem Lett. 2008 Jan 15;18(2):749-54. PubMed PMID: 18054227. 9: Zhang D, Raghavan N, Chen SY, Zhang H, Quan M, Lecureux L, Patrone LM, Lam PY, Bonacorsi SJ, Knabb RM, Skiles GL, He K. Reductive isoxazole ring opening of the anticoagulant razaxaban is the major metabolic clearance pathway in rats and dogs. Drug Metab Dispos. 2008 Feb;36(2):303-15. PubMed PMID: 17984286. 10: Varnes JG, Wacker DA, Jacobson IC, Quan ML, Ellis CD, Rossi KA, He MY, Luettgen JM, Knabb RM, Bai S, He K, Lam PY, Wexler RR. Design, structure-activity relationship, and pharmacokinetic profile of pyrazole-based indoline factor Xa inhibitors. Bioorg Med Chem Lett. 2007 Dec 1;17(23):6481-8. PubMed PMID: 17933529. 11: Pinto DJ, Orwat MJ, Koch S, Rossi KA, Alexander RS, Smallwood A, Wong PC, Rendina AR, Luettgen JM, Knabb RM, He K, Xin B, Wexler RR, Lam PY. Discovery of 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 (apixaban, BMS-562247), a highly potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation factor Xa. J Med Chem. 2007 Nov 1;50(22):5339-56. PubMed PMID: 17914785. 12: Wong PC, Crain EJ, Watson CA, Wexler RR, Lam PY, Quan ML, Knabb RM. Razaxaban, a direct factor Xa inhibitor, in combination with aspirin and/or clopidogrel improves low-dose antithrombotic activity without enhancing bleeding liability in rabbits. J Thromb Thrombolysis. 2007 Aug;24(1):43-51. PubMed PMID: 17323133. 13: Badawy SI, Gray DB, Zhao F, Sun D, Schuster AE, Hussain MA. Formulation of solid dosage forms to overcome gastric pH interaction of the factor Xa inhibitor, BMS-561389. Pharm Res. 2006 May;23(5):989-96. PubMed PMID: 16715389. 14: Quan ML, Han Q, Fevig JM, Lam PY, Bai S, Knabb RM, Luettgen JM, Wong PC, Wexler RR. Aminobenzisoxazoles with biaryl P4 moieties as potent, selective, and orally bioavailable factor Xa inhibitors. Bioorg Med Chem Lett. 2006 Apr 1;16(7):1795-8. PubMed PMID: 16434195. 15: Saiah E, Soares C. Small molecule coagulation cascade inhibitors in the clinic. Curr Top Med Chem. 2005;5(16):1677-95. Review. PubMed PMID: 16375748. 16: Gerotziafas GT, Samama MM. Heterogeneity of synthetic factor Xa inhibitors. Curr Pharm Des. 2005;11(30):3855-76. Review. PubMed PMID: 16305517. 17: Alexander JH, Singh KP. Inhibition of Factor Xa : a potential target for the development of new anticoagulants. Am J Cardiovasc Drugs. 2005;5(5):279-90. Review. PubMed PMID: 16156684. 18: Quan ML, Lam PY, Han Q, Pinto DJ, He MY, Li R, Ellis CD, Clark CG, Teleha CA, Sun JH, Alexander RS, Bai S, Luettgen JM, Knabb RM, Wong PC, Wexler RR. Discovery of 1-(3'-aminobenzisoxazol-5'-yl)-3-trifluoromethyl-N-[2-fluoro-4- [(2'-dimethylaminomethyl)imidazol-1-yl]phenyl]-1H-pyrazole-5-carboxyamide hydrochloride (razaxaban), a highly potent, selective, and orally bioavailable factor Xa inhibitor. J Med Chem. 2005 Mar 24;48(6):1729-44. PubMed PMID: 15771420. 19: Ansell J. New anticoagulants and their potential impact on the treatment of thromboembolic disease. Curr Hematol Rep. 2004 Sep;3(5):357-62. Review. PubMed PMID: 15341703. 20: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 May;26(4):295-318. PubMed PMID: 15319808.