An IP receptor agonist and active metabolite of NS-304
Related Products
Labeled Version(s)
43917MRE-269-d6
Pro-drug Form(s)
10010411NS 304
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MRE-269

Item No. 10010412

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[4-[(5,6-diphenylpyrazinyl)(1-methylethyl)amino]butoxy]-acetic acid
CAS Number
475085-57-5
Synonyms
  • ACT-333679
Molecular Formula
C25H29N3O3
Formula Weight
419.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 12 mg/mlEthanol: 15 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
231, 299, 366 nm
SMILES
OC(=O)COCCCCN(C(C)C)c1cnc(c2ccccc2)c(n1)c1ccccc1
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)
InChi Key
OJQMKCBWYCWFPU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    50 mg

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    Product Description

    MRE-269 is an IP receptor agonist and an active metabolite of NS 304 (Item No. 10010411).1 It is formed from NS 304 primarily via carboxylesterase 1 (CES1) in human liver microsomes and via CES2 in human intestinal microsomes.2 It binds to the IP receptor (Ki = 20 nM) and increases cAMP levels in human pulmonary artery smooth muscle cells (PASMCs) in a concentration-dependent manner.1,3 It is selective for the IP receptor over the DP receptor (IC50 = 2.6 µM), EP1, EP2, EP3, and EP4 receptors (IC50s = >10, 5.8, >10, and 4.9 µM, respectively), FP receptor (IC50 = >10 µM), and TP receptor (IC50 = >10 µM).1 Due to its selectivity for IP over EP3 receptors, MRE-269 induces vasodilation equally in both large and small isolated rat pulmonary arteries in a concentration-dependent manner.4 It also inhibits ADP-induced platelet aggregation in isolated human and rat platelet-rich plasma (IC50s = 0.21 and 10 µM, respectively).1 MRE-269 reduces PDGF-induced proliferation of primary PASMCs derived from patients with chronic thromboembolic pulmonary hypertension (CTEPH).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kuwano, K., Hashino, A., Asaki, T., et al. 2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide (NS-304), an orally available and long-acting prostacyclin receptor agonist prodrug. J. Pharmacol. Exp. Ther. 322(3), 1181-1188 (2007).

    2. Imai, S., Ichikawa, T., Sugiyama, C., et al. Contribution of human liver and intestinal carboxylesterases to the hydrolysis of selexipag in vitro. J. Pharm. Sci. 108(2), 1027-1034 (2019).

    3. Fuchikami, C., Murakami, K., Tajima, K., et al. A comparison of vasodilation mode among selexipag (NS-304; [2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide]), its active metabolite MRE-269 and various prostacyclin receptor agonists in rat, porcine and human pulmonary arteries. Eur. J. Pharmacol. 795, 75-83 (2017).

    4. Kuwano, K., Hashino, A., Noda, K., et al. A long-acting and highly selective prostacyclin receptor agonist prodrug, 2-{4-[5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide (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. 326(3), 691-699 (2008).

    5. Kuramoto, K., Ogawa, A., Kiyama, K., et al. Antiproliferative effect of selexipag active metabolite MRE-269 on pulmonary arterial smooth muscle cells from patients with chronic thromboembolic pulmonary hypertension. Pulm. Circ. 13(2), e12231 (2023).

    Product Citations

    Matsumoto, N., Singh, N., Lee, K.S., et al. The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms. Prostaglandins Other Lipid Mediat. 162, 106662 (2022).