Darexaban glucuronide

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

MedKoo CAT#: 326930

CAS#: 432029-12-4

Description: Darexaban glucuronide, also known as YM-222714, is the major component in plasma after oral administration of darexaban to humans and is the pharmacologically active metabolite. Darexaban (YM150) is a direct inhibitor of factor Xa. 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.

Chemical Structure

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Darexaban glucuronide
CAS# 432029-12-4
Instruction

Theoretical Analysis

MedKoo Cat#: 326930
Name: Darexaban glucuronide
CAS#: 432029-12-4
Chemical Formula: C33H38N4O10
Exact Mass: 650.26
Molecular Weight: 650.685
Elemental Analysis: C, 60.91; H, 5.89; N, 8.61; O, 24.59

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.

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Synonym: YM-222714; YM 222714; YM222714; Darexaban glucuronide

IUPAC/Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-(4-methoxybenzamido)-2-(4-(4-methyl-1,4-diazepan-1-yl)benzamido)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid

InChi Key: IOUMBCGOXOKZAE-CLIYFGAVSA-N

InChi Code: InChI=1S/C33H38N4O10/c1-36-15-4-16-37(18-17-36)21-11-7-19(8-12-21)31(42)35-25-23(34-30(41)20-9-13-22(45-2)14-10-20)5-3-6-24(25)46-33-28(40)26(38)27(39)29(47-33)32(43)44/h3,5-14,26-29,33,38-40H,4,15-18H2,1-2H3,(H,34,41)(H,35,42)(H,43,44)/t26-,27-,28+,29-,33+/m0/s1

SMILES Code: O[C@H]([C@H]([C@@H]([C@@H](C(O)=O)O1)O)O)[C@@H]1OC2=CC=CC(NC(C3=CC=C(OC)C=C3)=O)=C2NC(C4=CC=C(N5CCN(C)CCC5)C=C4)=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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 650.69 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: Ishihara T, Koga Y, Mori K, Sugasawa K, Iwatsuki Y, Hirayama F. Novel strategy to boost oral anticoagulant activity of blood coagulation enzyme inhibitors based on biotransformation into hydrophilic conjugates. Bioorg Med Chem. 2014 Nov 15;22(22):6324-32. doi: 10.1016/j.bmc.2014.09.059. Epub 2014 Oct 19. PubMed PMID: 25438755.

2: Groenendaal D, Strabach G, Garcia-Hernandez A, Kadokura T, Heeringa M, Mol R, Eltink C, Onkels H. The pharmacokinetics of darexaban (YM150), an oral direct factor Xa inhibitor, are not affected by ketoconazole, a strong inhibitor of CYP3A and P-glycoprotein. Clin Pharmacol Drug Dev. 2014 May;3(3):194-201. doi: 10.1002/cpdd.93. Epub 2014 Mar 3. PubMed PMID: 27128609.

3: Kadokura T, Oikawa K, Miyata K, Murase T, Nakamura M. Clinical Pharmacokinetics, Pharmacodynamics, Safety and Tolerability of Darexaban, an Oral Direct Factor Xa Inhibitor, in Healthy Elderly Japanese Subjects. Clin Pharmacol Drug Dev. 2013 Oct;2(4):328-35. doi: 10.1002/cpdd.50. Epub 2013 Aug 16. PubMed PMID: 27121937.

4: 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.

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: 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.

10: 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.

11: 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.

12: 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.

13: 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.