MRE-269
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MedKoo CAT#: 522411

CAS#: 475085-57-5

Description: MRE-269, also known as ACT-333679, is a long-acting and highly selective prostacyclin receptor agonist. MRE-269, the active form or metabolite of Selexipag (NS-304), is much more selective for the IP receptor than are the prostacyclin analogs beraprost and iloprost, which also have high affinity for the EP(3) receptor.


Chemical Structure

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MRE-269
CAS# 475085-57-5

Theoretical Analysis

MedKoo Cat#: 522411
Name: MRE-269
CAS#: 475085-57-5
Chemical Formula: C25H29N3O3
Exact Mass: 419.22089
Molecular Weight: 419.52
Elemental Analysis: C, 71.57; H, 6.97; N, 10.02; O, 11.44

Price and Availability

Size Price Availability Quantity
5.0mg USD 310.0 2 Weeks
10.0mg USD 540.0 2 Weeks
50.0mg USD 1700.0 2 Weeks
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Synonym: MRE-269; MRE269; MRE 269; ACT-333679; ACT 333679; ACT333679.

IUPAC/Chemical Name: 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)acetic acid

InChi Key: OJQMKCBWYCWFPU-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H29N3O3/c1-19(2)28(15-9-10-16-31-18-23(29)30)22-17-26-24(20-11-5-3-6-12-20)25(27-22)21-13-7-4-8-14-21/h3-8,11-14,17,19H,9-10,15-16,18H2,1-2H3,(H,29,30)

SMILES Code: CC(N(CCCCOCC(O)=O)C1=NC(C2=CC=CC=C2)=C(C3=CC=CC=C3)N=C1)C

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

Preparing Stock Solutions

The following data is based on the product molecular weight 419.52 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: Asaki T, Kuwano K, Morrison K, Gatfield J, Hamamoto T, Clozel M. Selexipag: An Oral and Selective IP Prostacyclin Receptor Agonist for the Treatment of Pulmonary Arterial Hypertension. J Med Chem. 2015 Sep 24;58(18):7128-37. doi: 10.1021/acs.jmedchem.5b00698. Epub 2015 Sep 16. PubMed PMID: 26291199.

2: Skoro-Sajer N, Lang IM. Selexipag for the treatment of pulmonary arterial hypertension. Expert Opin Pharmacother. 2014 Feb;15(3):429-36. doi: 10.1517/14656566.2014.876007. Epub 2014 Jan 7. Review. PubMed PMID: 24392948.

3: Orie NN, Ledwozyw A, Williams DJ, Whittle BJ, Clapp LH. Differential actions of the prostacyclin analogues treprostinil and iloprost and the selexipag metabolite, MRE-269 (ACT-333679) in rat small pulmonary arteries and veins. Prostaglandins Other Lipid Mediat. 2013 Oct;106:1-7. doi: 10.1016/j.prostaglandins.2013.07.003. Epub 2013 Jul 18. PubMed PMID: 23872196.

4: Benyahia C, Boukais K, Gomez I, Silverstein A, Clapp L, Fabre A, Danel C, Leséche G, Longrois D, Norel X. A comparative study of PGI2 mimetics used clinically on the vasorelaxation of human pulmonary arteries and veins, role of the DP-receptor. Prostaglandins Other Lipid Mediat. 2013 Dec;107:48-55. doi: 10.1016/j.prostaglandins.2013.07.001. Epub 2013 Jul 12. PubMed PMID: 23850788.

5: Kotzki S, Roustit M, Arnaud C, Boutonnat J, Blaise S, Godin-Ribuot D, Cracowski JL. Anodal iontophoresis of a soluble guanylate cyclase stimulator induces a sustained increase in skin blood flow in rats. J Pharmacol Exp Ther. 2013 Sep;346(3):424-31. doi: 10.1124/jpet.113.205484. Epub 2013 Jul 9. PubMed PMID: 23838678.

6: Morrison K, Studer R, Ernst R, Haag F, Kauser K, Clozel M. Differential effects of Selexipag [corrected] and prostacyclin analogs in rat pulmonary artery. J Pharmacol Exp Ther. 2012 Dec;343(3):547-55. doi: 10.1124/jpet.112.197152. Epub 2012 Aug 23. Erratum in: J Pharmacol Exp Ther. 2013 Jan;344(1):317. PubMed PMID: 22918043.

7: Van Ly D, Burgess JK, Brock TG, Lee TH, Black JL, Oliver BG. Prostaglandins but not leukotrienes alter extracellular matrix protein deposition and cytokine release in primary human airway smooth muscle cells and fibroblasts. Am J Physiol Lung Cell Mol Physiol. 2012 Aug 1;303(3):L239-50. doi: 10.1152/ajplung.00097.2012. Epub 2012 May 25. PubMed PMID: 22637153.

8: Liu B, Luo W, Zhang Y, Li H, Zhu N, Huang D, Zhou Y. Role of cyclooxygenase-1-mediated prostacyclin synthesis in endothelium-dependent vasoconstrictor activity of porcine interlobular renal arteries. Am J Physiol Renal Physiol. 2012 May 1;302(9):F1133-40. doi: 10.1152/ajprenal.00604.2011. Epub 2012 Feb 1. PubMed PMID: 22301626.

9: Morrison K, Ernst R, Hess P, Studer R, Clozel M. Selexipag: a selective prostacyclin receptor agonist that does not affect rat gastric function. J Pharmacol Exp Ther. 2010 Oct;335(1):249-55. doi: 10.1124/jpet.110.169748. Epub 2010 Jul 21. PubMed PMID: 20660124.

10: Kuwano K, Hashino A, Noda K, Kosugi K, Kuwabara K. A long-acting and highly selective prostacyclin receptor agonist prodrug, 2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetam ide (NS-304), ameliorates rat pulmonary hypertension with unique relaxant responses of its active form, {4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}acetic acid (MRE-269), on rat pulmonary artery. J Pharmacol Exp Ther. 2008 Sep;326(3):691-9. doi: 10.1124/jpet.108.138305. Epub 2008 Jun 13. PubMed PMID: 18552131.

11: Kuwano K, Hashino A, Asaki T, Hamamoto T, Yamada T, Okubo K, Kuwabara K. 2-[4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy]-N-(methylsulfonyl)acetam ide (NS-304), an orally available and long-acting prostacyclin receptor agonist prodrug. J Pharmacol Exp Ther. 2007 Sep;322(3):1181-8. Epub 2007 Jun 1. PubMed PMID: 17545310.

MRE-269

5.0mg / USD 310.0