Razaxaban HCl
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MedKoo CAT#: 328086

CAS#: 405940-76-3 (HCl)

Description: Razaxaban, also known as BMS-561389; BMS-561389-01; DPC-906; BMS-561389-06, is a factor Xa inhibitor potentially for the treatment of thrombosis. Razaxaban was an effective antithrombotic agent in a rabbit model of arterial thrombosis. Low-dose razaxaban was useful in combination with sub-optimal doses of aspirin and/or clopidogrel for the prevention of occlusive arterial thrombosis without excessive bleeding.


Chemical Structure

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Razaxaban HCl
CAS# 405940-76-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 328086
Name: Razaxaban HCl
CAS#: 405940-76-3 (HCl)
Chemical Formula: C24H21ClF4N8O2
Exact Mass: 0.00
Molecular Weight: 564.930
Elemental Analysis: C, 51.03; H, 3.75; Cl, 6.28; F, 13.45; N, 19.84; O, 5.66

Price and Availability

Size Price Availability Quantity
5mg USD 250
10mg USD 450
25mg USD 950
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Related CAS #: 218298-21-6 (free base)   405940-76-3 (HCl)    

Synonym: Razaxaban hydrochloride; BMS-561389; BMS-561389-01; DPC-906; BMS-561389-06; BMS561389; BMS561389-01; DPC906; BMS561389-06.

IUPAC/Chemical Name: 1H-Pyrazole-5-carboxamide, 1-(3-amino-1,2-benzisoxazol-5-yl)-N-(4-(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-2-fluorophenyl)-3-(trifluoromethyl)-, monohydrochloride

InChi Key: CASCTHHMARGRLB-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H20F4N8O2.ClH/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);1H

SMILES Code: O=C(C1=CC(C(F)(F)F)=NN1C2=CC3=C(ON=C3N)C=C2)NC4=CC=C(N5C=CN=C5CN(C)C)C=C4F.[H]Cl

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: 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: Related CAS# 218298-21-6 (Razaxaban) 405940-76-3 (Razaxaban hydrochloride)

Biological target: Razaxaban hydrochloride (BMS 561389 hydrochloride) is a highly potent, selective and orally active factor Xa inhibitor with a Ki of 0.19 nM. Razaxaban hydrochloride exhibits excellent selectivity (>5000-fold) for factor Xa over other related serine proteases. Razaxaban hydrochloride is also a potent thrombin inhibitor with a Ki of 540 nM. Razaxaban hydrochloride has strongly antithrombotic activity.
In vitro activity: On the basis of razaxaban’s excellent in vitro potency and selectivity profile, high free fraction in human plasma, good oral bioavailability, and in vivo efficacy in antithrombotic models, razaxaban HCl was selected for clinical development as razaxaban (DPC 906, BMS-561389). Reference: J Med Chem. 2005 Mar 24;48(6):1729-44. https://pubmed.ncbi.nlm.nih.gov/15771420/
In vivo activity: Razaxaban inhibited thrombus and fibrin formation at the highest concentrations tested in this study. No difference in drug effect was apparent at different axial positions. Reference: J Thromb Thrombolysis. 2012 Jan;33(1):6-15. https://pubmed.ncbi.nlm.nih.gov/22120925/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
To be determined 0.0 0.00

Preparing Stock Solutions

The following data is based on the product molecular weight 564.93 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. 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. doi: 10.1021/jm0497949. PMID: 15771420. 2. 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. PMID: 22120925. 3. 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. doi: 10.1124/dmd.107.018416. Epub 2007 Nov 5. PMID: 17984286.
In vitro protocol: 1. 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. doi: 10.1021/jm0497949. PMID: 15771420.
In vivo protocol: 1. 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. PMID: 22120925. 2. 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. doi: 10.1124/dmd.107.018416. Epub 2007 Nov 5. PMID: 17984286.

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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.