Atecegatran metoxil | AZD0837 | CAS#433937-93-0

MedKoo Cat#: 319784 | Name: Atecegatran metoxil

Description:

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

Atecegatran metoxil, also known as Atecegatran fexenetil and AZD0837, is an oral direct thrombin inhibitor currently in clinical development for the prevention of stroke and systemic embolic events in patients with atrial fibrillation. AZD0837 is bioconverted to AR-H067637, a selective and reversible direct thrombin inhibitor. AZD0837 single oral doses (15 - 750 mg) are well tolerated in healthy male subjects and exhibit favorable PK properties and reproducible effects on ex vivo coagulation time variables that support further clinical development.

Chemical Structure

Atecegatran metoxil

CAS#433937-93-0

Theoretical Analysis

MedKoo Cat#: 319784

Name: Atecegatran metoxil

CAS#: 433937-93-0

Chemical Formula: C22H23ClF2N4O5

Exact Mass: 496.1325

Molecular Weight: 496.90

Elemental Analysis: C, 53.18; H, 4.67; Cl, 7.13; F, 7.65; N, 11.28; O, 16.10

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

AZD0837; AZD-0837; AZD 0837; Atecegatran metoxil; Atecegatran fexenetil.

IUPAC/Chemical Name

(S)-1-((R)-2-(3-chloro-5-(difluoromethoxy)phenyl)-2-hydroxyacetyl)-N-(4-(N-methoxycarbamimidoyl)benzyl)azetidine-2-carboxamide

InChi Key

XSNMGLZVFNDDPW-ZWKOTPCHSA-N

InChi Code

InChI=1S/C22H23ClF2N4O5/c1-33-28-19(26)13-4-2-12(3-5-13)11-27-20(31)17-6-7-29(17)21(32)18(30)14-8-15(23)10-16(9-14)34-22(24)25/h2-5,8-10,17-18,22,30H,6-7,11H2,1H3,(H2,26,28)(H,27,31)/t17-,18+/m0/s1

SMILES Code

O=C([C@H]1N(C([C@@H](C2=CC(OC(F)F)=CC(Cl)=C2)O)=O)CC1)NCC3=CC=C(C(NOC)=N)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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 496.90 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.

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: Lip GY, Rasmussen LH, Olsson SB, Jensen E, Hamrén B, Eriksson UG, Wåhlander K. Exposure-response for biomarkers of anticoagulant effects by the oral direct thrombin inhibitor AZD0837 in patients with atrial fibrillation. Br J Clin Pharmacol. 2015 Dec;80(6):1362-73. doi: 10.1111/bcp.12719. Epub 2015 Sep 22. PubMed PMID: 26174611. 2: Dunér K, Hulthe J, Tranberg M. Determination of the thrombin inhibitor AZD0837 and its metabolites in human bile using mixed mode solid phase extraction and LC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Sep 1;904:29-34. doi: 10.1016/j.jchromb.2012.06.026. Epub 2012 Jun 28. PubMed PMID: 22871267. 3: Wolzt M, Eriksson UG, Gouya G, Leuchten N, Kapiotis S, Elg M, Schützer KM, Zetterstrand S, Holmberg M, Wåhlander K. Effect on perfusion chamber thrombus size in patients with atrial fibrillation during anticoagulant treatment with oral direct thrombin inhibitors, AZD0837 or ximelagatran, or with vitamin K antagonists. Thromb Res. 2012 Apr;129(4):e83-91. doi: 10.1016/j.thromres.2011.08.018. Epub 2011 Sep 16. PubMed PMID: 21925716. 4: Johansson S, Cullberg M, Eriksson UG, Elg M, Dunér K, Jensen E, Wollbratt M, Wåhlander K. Single-dose pharmacokinetics, pharmacodynamics and safety of AZD0837, a novel oral direct thrombin inhibitor, in young healthy male subjects. Int J Clin Pharmacol Ther. 2011 Apr;49(4):258-67. doi: 10.5414/CP201465. PubMed PMID: 21429440. 5: Lip GY, Rasmussen LH, Olsson SB, Zetterstrand S, Stahre C, Bylock A, Aunes-Jansson M, Eriksson U, Wåhlander K; Steering Committee. Oral direct thrombin inhibitor AZD0837 for the prevention of stroke and systemic embolism in patients with non-valvular atrial fibrillation: a Phase II study of AZD0837 in patients who are appropriate for but unable or unwilling to take vitamin K antagonist therapy. Thromb Res. 2011 Feb;127(2):91-9. doi: 10.1016/j.thromres.2010.11.012. Epub 2010 Dec 18. PubMed PMID: 21172721. 6: Matsson EM, Palm JE, Eriksson UG, Bottner P, Lundahl A, Knutson L, Lennernäs H. Effects of ketoconazole on the in vivo biotransformation and hepatobiliary transport of the thrombin inhibitor AZD0837 in pigs. Drug Metab Dispos. 2011 Feb;39(2):239-46. doi: 10.1124/dmd.110.035022. Epub 2010 Oct 26. PubMed PMID: 20978106. 7: Pehrsson S, Johansson K, Kjaer M, Elg M. Evaluation of AR-H067637, the active metabolite of the new direct thrombin inhibitor AZD0837, in models of venous and arterial thrombosis and bleeding in anaesthetised rats. Thromb Haemost. 2010 Dec;104(6):1242-9. doi: 10.1160/TH09-10-0744. Epub 2010 Aug 30. PubMed PMID: 20806126. 8: Schützer KM, Svensson MK, Zetterstrand S, Eriksson UG, Wåhlander K. Reversible elevations of serum creatinine levels but no effect on glomerular filtration during treatment with the direct thrombin inhibitor AZD0837. Eur J Clin Pharmacol. 2010 Sep;66(9):903-10. doi: 10.1007/s00228-010-0849-7. Epub 2010 Jun 10. PubMed PMID: 20535457. 9: Walfridsson H, Johansson B, Englund A, Kennebäck G, Schwieler J, Kongstad O, Wåhlander K, Malm AR, Edvardsson N. Effects of AZD0837, a novel direct thrombin inhibitor, on the electrophysiological properties of the human heart: a randomized, double-blind, parallel-group, placebo-controlled study. Clin Drug Investig. 2010;30(7):461-71. doi: 10.2165/11536300-000000000-00000. PubMed PMID: 20528001. 10: Olsson SB, Rasmussen LH, Tveit A, Jensen E, Wessman P, Panfilov S, Wåhlander K. Safety and tolerability of an immediate-release formulation of theoral direct thrombin inhibitor AZD0837 in the prevention of stroke and systemic embolism in patients with atrial fibrillation. Thromb Haemost. 2010 Mar;103(3):604-12. doi: 10.1160/TH09-07-0509. Epub 2010 Jan 13. PubMed PMID: 20076850. 11: Lip GY, Rasmussen LH, Olsson SB, Jensen EC, Persson AL, Eriksson U, Wåhlander KF; Steering Committee. Oral direct thrombin inhibitor AZD0837 for the prevention of stroke and systemic embolism in patients with non-valvular atrial fibrillation: a randomized dose-guiding, safety, and tolerability study of four doses of AZD0837 vs. vitamin K antagonists. Eur Heart J. 2009 Dec;30(23):2897-907. doi: 10.1093/eurheartj/ehp318. Epub 2009 Aug 18. PubMed PMID: 19690349; PubMed Central PMCID: PMC2785945.