Letaxaban

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MedKoo CAT#: 205895

CAS#: 870262-90-1

Description: Letaxaban, also known as TAK-442, is a potent, selective, and orally active factor Xa inhibitor, which is a tetrahydropyrimidin-2(1H)-one derivative. TAK-442 inhibited endogenous FXa activity in platelet-poor human [half-maximal inhibitory concentration (IC(50)): 53 nM, TAK-442 ] and rat (IC(50): 32 nM, TAK-442 ) plasma. TAK-442 inhibited in vitro reconstituted human prothrombinase (system included FXa, calcium, and washed platelets) with an IC(50) value of 51 nM. In a rat model of balloon injury, thrombin activity on the surface of injured vessels increased to 3.2-, 22-, and 5.8-fold the activity on the surface of the intact aorta at 5 minutes, 1 hour, and 24 hours after the injury, respectively. At approximately 1 hour after the injury, TAK-442 blocked platelet-associated thrombin generation on the surface of injured aortas with an IC(50) value of 19 nM. (source: J Cardiovasc Pharmacol. 2011 Feb;57(2):201-6.)


Chemical Structure

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Letaxaban
CAS# 870262-90-1

Theoretical Analysis

MedKoo Cat#: 205895
Name: Letaxaban
CAS#: 870262-90-1
Chemical Formula: C22H26ClN3O5S
Exact Mass: 479.12817
Molecular Weight: 479.98
Elemental Analysis: C, 55.05; H, 5.46; Cl, 7.39; N, 8.75; O, 16.67; S, 6.68

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Synonym: Letaxaban TAK442; TAK 442; TAK-442.

IUPAC/Chemical Name: (S)-1-(1-(3-((6-chloronaphthalen-2-yl)sulfonyl)-2-hydroxypropanoyl)piperidin-4-yl)tetrahydropyrimidin-2(1H)-one

InChi Key: GEHAEMCVKDPMKO-HXUWFJFHSA-N

InChi Code: InChI=1S/C22H26ClN3O5S/c23-17-4-2-16-13-19(5-3-15(16)12-17)32(30,31)14-20(27)21(28)25-10-6-18(7-11-25)26-9-1-8-24-22(26)29/h2-5,12-13,18,20,27H,1,6-11,14H2,(H,24,29)/t20-/m1/s1

SMILES Code: O=C1NCCCN1C2CCN(C([C@H](O)CS(=O)(C3=CC=C4C=C(Cl)C=CC4=C3)=O)=O)CC2

Appearance: Solid powder

Purity: >98%

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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 479.98 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

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1: Deftereos S, Bouras G, Giannopoulos G, Kossyvakis C, Panagopoulou V, Pyrgakis V, Stefanadis C. Novel oral anticoagulants in the treatment of acute coronary syndromes: is there any room for new anticoagulants? Curr Clin Pharmacol. 2012 Aug;7(3):195-208. PubMed PMID: 22564121.

2: Konishi N, Hiroe K, Kawamura M. Effects of fondaparinux and a direct factor Xa inhibitor TAK-442 on platelet-associated prothrombinase in the balloon-injured artery of rats. J Cardiovasc Pharmacol. 2011 Feb;57(2):201-6. PubMed PMID: 21052010.

3: Zufferey PJ, Samama CM, Rosencher N. Improve the results of phase II trials of thromboprophylaxis with the new oral anticoagulant drugs. Thromb Haemost. 2010 Dec;104(6):1083-4. Epub 2010 Sep 30. PubMed PMID: 20886198.

4: Weitz JI, Cao C, Eriksson BI, Fisher W, Kupfer S, Raskob G, Spaeder J, Turpie AG. A dose-finding study with TAK-442, an oral factor Xa inhibitor, in patients undergoing elective total knee replacement surgery. Thromb Haemost. 2010 Dec;104(6):1150-7. Epub 2010 Sep 30. PubMed PMID: 20886185.

5: Konishi N, Hiroe K, Kawamura M. Differential effects of TAK-442, a novel orally active direct factor Xa inhibitor, and ximelagatran, a thrombin inhibitor, on factor V-mediated feedback on coagulation cascade and bleeding. Thromb Haemost. 2010 Sep;104(3):504-13. Epub 2010 Jul 20. PubMed PMID: 20664909.

6: Konishi N, Hiroe K, Kawamura M. Synergistic effect of a factor Xa inhibitor, TAK-442, and antiplatelet agents on whole blood coagulation and arterial thrombosis in rats. Thromb Res. 2010 Aug;126(2):124-9. Epub 2010 May 10. PubMed PMID: 20452654.

7: Kawamura M, Konishi N, Hiroe K, Shofuda K, Imaeda Y, Fujimoto T, Kubo K. Antithrombotic and anticoagulant profiles of TAK-442, a novel factor Xa inhibitor, in a rabbit model of venous thrombosis. J Cardiovasc Pharmacol. 2010 Aug;56(2):156-61. Erratum in: J Cardiovasc Pharmacol. 2010 Oct;56(4):439. PubMed PMID: 20410831.

8: Fujimoto T, Imaeda Y, Konishi N, Hiroe K, Kawamura M, Textor GP, Aertgeerts K, Kubo K. Discovery of a tetrahydropyrimidin-2(1H)-one derivative (TAK-442) as a potent, selective, and orally active factor Xa inhibitor. J Med Chem. 2010 May 13;53(9):3517-31. PubMed PMID: 20355714.

9: Perzborn E. Factor Xa inhibitors--new anticoagulants for secondary haemostasis. Hamostaseologie. 2009 Aug;29(3):260-7. PubMed PMID: 19644596.

10: Gómez-Outes A, Lecumberri R, Pozo C, Rocha E. New anticoagulants: focus on venous thromboembolism. Curr Vasc Pharmacol. 2009 Jul;7(3):309-29. Review. PubMed PMID: 19601856.

11: Eriksson BI, Quinlan DJ, Weitz JI. Comparative pharmacodynamics and pharmacokinetics of oral direct thrombin and factor xa inhibitors in development. Clin Pharmacokinet. 2009;48(1):1-22. doi: 10.2165/0003088-200948010-00001. Review. PubMed PMID: 19071881.
  

Letaxaban

10.0mg / Not available


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