Darexaban

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

MedKoo CAT#: 319843

CAS#: 365462-23-3

Description: Darexaban, also known as Tanexaban and YM-150, is a direct inhibitor of factor Xa created by Astellas Pharma. Darexaban and darexaban glucuronide selectively and competitively inhibit FXa, suppressing prothrombin activity at the sites of blood clot (thrombus) formation. This leads to a decrease in blood clot formation in a dose dependent manner. Reducing blood clot formation will decrease blood flow blockages, thus possibly lowering the risk of myocardial infarction, unstable angina, venous thrombosis, and ischemic stroke.

Chemical Structure

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Darexaban
CAS# 365462-23-3
Instruction

Theoretical Analysis

MedKoo Cat#: 319843
Name: Darexaban
CAS#: 365462-23-3
Chemical Formula: C27H30N4O4
Exact Mass: 474.23
Molecular Weight: 474.561
Elemental Analysis: C, 68.34; H, 6.37; N, 11.81; O, 13.49

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: YM150; YM 150; YM150; Darexaban, Tanexaban.

IUPAC/Chemical Name: N-(2-Hydroxy-6-(4-methoxybenzamido)phenyl)-4-(4-methyl-1,4-diazepan-1-yl)benzamide

InChi Key: IJNIQYINMSGIPS-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H30N4O4/c1-30-15-4-16-31(18-17-30)21-11-7-19(8-12-21)27(34)29-25-23(5-3-6-24(25)32)28-26(33)20-9-13-22(35-2)14-10-20/h3,5-14,32H,4,15-18H2,1-2H3,(H,28,33)(H,29,34)

SMILES Code: O=C(NC1=C(NC(C2=CC=C(OC)C=C2)=O)C=CC=C1O)C3=CC=C(N4CCN(C)CCC4)C=C3

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: It is an experimental drug that acts as an anticoagulant and antithrombotic to prevent venous thromboembolism after a major orthopaedic surgery, stroke in patients with atrial fibrillation and possibly ischemic events in acute coronary syndrome. It is used in form of the maleate. The development of darexaban was discontinued in September 2011.

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 474.56 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:
In vitro protocol:
In vivo protocol:

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1: Lip GY, Halperin JL, Petersen P, Rodgers GM, Pall D, Renfurm RW. A Phase II, double-blind, randomized, parallel group, dose-finding study of the safety and tolerability of darexaban compared with warfarin in patients with non-valvular atrial fibrillation: the oral factor Xa inhibitor for prophylaxis of stroke in atrial fibrillation study 2 (OPAL-2). J Thromb Haemost. 2015 Aug;13(8):1405-13. doi: 10.1111/jth.13025. Epub 2015 Jul 15. PubMed PMID: 26052866.

2: Eriksson BI, Agnelli G, Gallus AS, Lassen MR, Prins MH, Renfurm RW, Kashiwa M, Turpie AG. Darexaban (YM150) versus enoxaparin for the prevention of venous thromboembolism after total hip arthroplasty: a randomised phase IIb dose confirmation study (ONYX-3). Thromb Haemost. 2014 Feb;111(2):213-25. doi: 10.1160/TH13-04-0296. Epub 2013 Oct 17. PubMed PMID: 24136153.

3: Kadokura T, Kashiwa M, Groenendaal D, Heeringa M, Mol R, Verheggen F, Garcia-Hernandez A, Onkels H. Clinical pharmacokinetics, pharmacodynamics, safety and tolerability of darexaban, an oral direct factor Xa inhibitor, in healthy Caucasian and Japanese subjects. Biopharm Drug Dispos. 2013 Nov;34(8):431-41. doi: 10.1002/bdd.1858. Epub 2013 Sep 20. PubMed PMID: 23929659.

4: Kadokura T, Groenendaal D, Heeringa M, Mol R, Verheggen F, Garcia-Hernandez A, Onkels H. Darexaban (YM150), an oral direct factor Xa inhibitor, has no effect on the pharmacokinetics of digoxin. Eur J Drug Metab Pharmacokinet. 2014 Mar;39(1):1-9. doi: 10.1007/s13318-013-0141-1. Epub 2013 Jun 11. PubMed PMID: 23754514.

5: Kaku S, Suzuki M, Saitoh M, Funatsu T, Uemura T, Suzuki K, Iwatsuki Y, Kawasaki T. Darexaban: anticoagulant effects in mice and human plasma in vitro, antithrombotic effects in thrombosis and bleeding models in mice and effects of anti-inhibitor coagulant complex and recombinant factor VIIa. Thromb Res. 2013 May;131(5):450-6. doi: 10.1016/j.thromres.2013.03.016. Epub 2013 Apr 13. PubMed PMID: 23591155.

6: Kadokura T, Taniuchi Y, Inoue H, Saito M, Iwahana M, Yamada S, Urae A, Nakamura M. Effect of food on the pharmacokinetics of darexaban, an oral direct factor Xa inhibitor, in healthy Japanese subjects. Int J Clin Pharmacol Ther. 2013 Mar;51(3):200-6. doi: 10.5414/CP201804. PubMed PMID: 23211396.

7: Kaku S, Uemura T, Saitoh M, Suzuki K, Iwatsuki Y, Funatsu T, Kawasaki T. Antithrombotic and anticoagulant effects of direct factor Xa inhibitor darexaban in rat and rabbit models of venous thrombosis. Eur J Pharmacol. 2013 Jan 15;699(1-3):40-7. doi: 10.1016/j.ejphar.2012.11.026. Epub 2012 Nov 29. PubMed PMID: 23200896.

8: Hashimoto T, Suzuki K, Kihara Y, Iwatsubo T, Miyashita A, Heeringa M, Onkels H, Groenendaal D, Verheggen F, van Marle S, Usui T. Absorption, metabolism and excretion of darexaban (YM150), a new direct factor Xa inhibitor in humans. Xenobiotica. 2013 Jun;43(6):534-47. doi: 10.3109/00498254.2012.738045. Epub 2012 Nov 20. PubMed PMID: 23167531.

9: Fuji T, Nakamura M, Takeuchi M. Darexaban for the prevention of venous thromboembolism in Asian patients undergoing orthopedic surgery: results from 2 randomized, placebo-controlled, double-blind studies. Clin Appl Thromb Hemost. 2014 Mar;20(2):199-211. doi: 10.1177/1076029612457810. Epub 2012 Sep 4. PubMed PMID: 22952213.

10: Sakon M, Nakamura M. Darexaban (YM150) prevents venous thromboembolism in Japanese patients undergoing major abdominal surgery: Phase III randomized, mechanical prophylaxis-controlled, open-label study. Thromb Res. 2012 Sep;130(3):e52-9. doi: 10.1016/j.thromres.2012.06.009. Epub 2012 Jul 2. PubMed PMID: 22762942.

11: Groenendaal D, Strabach G, Garcia-Hernandez A, Kadokura T, Heeringa M, Mol R, Eltink C, Onkels H. The pharmacokinetics of darexaban are not affected to a clinically relevant degree by rifampicin, a strong inducer of P-glycoprotein and CYP3A4. Br J Clin Pharmacol. 2013 Feb;75(2):440-9. doi: 10.1111/j.1365-2125.2012.04346.x. PubMed PMID: 22642721; PubMed Central PMCID: PMC3579259.

12: Apostolakis S, Lip GY. Novel oral anticoagulants: focus on the direct factor Xa inhibitor darexaban. Expert Opin Investig Drugs. 2012 Jul;21(7):1057-64. doi: 10.1517/13543784.2012.689286. Epub 2012 May 23. Review. PubMed PMID: 22616561.

13: Shiraga T, Yajima K, Teragaki T, Suzuki K, Hashimoto T, Iwatsubo T, Miyashita A, Usui T. Identification of enzymes responsible for the N-oxidation of darexaban glucuronide, the pharmacologically active metabolite of darexaban, and the glucuronidation of darexaban N-oxides in human liver microsomes. Biol Pharm Bull. 2012;35(3):413-21. PubMed PMID: 22382330.

14: Funatsu T, Iwatsuki Y, Kaku S. Darexaban has high sensitivity in the prothrombin time clotting test. J Thromb Haemost. 2012 Apr;10(4):703-5. doi: 10.1111/j.1538-7836.2012.04655.x. PubMed PMID: 22329675.

15: Iwatsuki Y, Sato T, Moritani Y, Shigenaga T, Suzuki M, Kawasaki T, Funatsu T, Kaku S. Biochemical and pharmacological profile of darexaban, an oral direct factor Xa inhibitor. Eur J Pharmacol. 2011 Dec 30;673(1-3):49-55. doi: 10.1016/j.ejphar.2011.10.009. Epub 2011 Oct 21. PubMed PMID: 22040919.

16: Shiraga T, Yajima K, Suzuki K, Suzuki K, Hashimoto T, Iwatsubo T, Miyashita A, Usui T. Identification of UDP-glucuronosyltransferases responsible for the glucuronidation of darexaban, an oral factor Xa inhibitor, in human liver and intestine. Drug Metab Dispos. 2012 Feb;40(2):276-82. doi: 10.1124/dmd.111.042614. Epub 2011 Oct 26. PubMed PMID: 22031623.

17: Hirayama F, Koshio H, Ishihara T, Hachiya S, Sugasawa K, Koga Y, Seki N, Shiraki R, Shigenaga T, Iwatsuki Y, Moritani Y, Mori K, Kadokura T, Kawasaki T, Matsumoto Y, Sakamoto S, Tsukamoto S. Discovery of N-[2-hydroxy-6-(4-methoxybenzamido)phenyl]-4- (4-methyl-1,4-diazepan-1-yl)benzamide (darexaban, YM150) as a potent and orally available factor Xa inhibitor. J Med Chem. 2011 Dec 8;54(23):8051-65. doi: 10.1021/jm200868m. Epub 2011 Nov 11. PubMed PMID: 21995444.

18: Kristensen SD. On the cutting edge of acute coronary syndromes: adding oral factor Xa-inhibition with darexaban to dual antiplatelet therapy: the RUBY-1 trial. Eur Heart J. 2011 Oct;32(20):2486-8. doi: 10.1093/eurheartj/ehr314. Epub 2011 Aug 30. PubMed PMID: 21878435.

19: Steg PG, Mehta SR, Jukema JW, Lip GY, Gibson CM, Kovar F, Kala P, Garcia-Hernandez A, Renfurm RW, Granger CB; RUBY-1 Investigators. RUBY-1: a randomized, double-blind, placebo-controlled trial of the safety and tolerability of the novel oral factor Xa inhibitor darexaban (YM150) following acute coronary syndrome. Eur Heart J. 2011 Oct;32(20):2541-54. doi: 10.1093/eurheartj/ehr334. Epub 2011 Aug 30. PubMed PMID: 21878434; PubMed Central PMCID: PMC3295208.