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MRE-269 Exclusive

Cayman Chemical Item Number 10010412

(CAS 475085-57-5)

MRE-269 (CAS 475085-57-5)

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Description

Prostacyclin (PGI2) is a potent vasorelaxant and inhibitor of platelet aggregation. It mediates its actions by binding to a specific G protein-coupled receptor, the IP receptor, on the surface of endothelial cells, arterial smooth muscle, and platelets.1 The IP receptor also participates in signal transduction of the pain response, cardioprotection, and inflammation.2,3,4,5 MRE-269 is the active form of the prodrug NS-304. It is a potent and selective agonist for the human IP receptor with a Ki value of 20 nM.6 In contrast to PGI2, which has a half-life of 30 seconds to a few minutes in vivo, plasma concentrations of MRE-269 remain near peak levels for more than eight hours in rats and dogs.6 Unlike the PGI2 analogues, beraprost and iloprost, MRE-269 lacks high affinity for the EP3 receptor.7 As a result, MRE-269 induces vasodilation equally in large and small pulmonary arteries, whereas vasodilation of small arteries by beraprost and iloprost is reduced via EP3-mediated vasoconstriction.7

1 Aristoff, P.A., Johnson, P.D., and Harrison, A.W. Synthesis of 9-substituted carbacyclin analogues. J Org Chem 48 5341-5348 (1983).

2 Murata, T., Ushikubi, F., Matsuoka, T., et al. Altered pain perception and inflammatory response in mice lacking prostacyclin receptor. Nature 388 678-682 (1997).

3 Cheng, Y., Austin, S.C., Rocca, B., et al. Role of prostacyclin in the cardiovascular response to thromboxane A2. Science 296 539-541 (2002).

4 Cui, Y., Kataoka, Y., Satoh, T., et al. Protective effect of prostaglandin I2 analogs on ischemic delayed neuronal damage in gerbils. Biochem Biophys Res Commun 265 301-304 (1999).

5 McLaughlin, V.V., Genthner, D.E., Panella, M.M., et al. Reduction in pulmonary vascular resistance with long-term epoprostenol (prostacyclin) therapy in primary pulmonary hypertension. N Engl J Med 338 273-277 (1998).

6 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).

7 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).

Formal Name [4-​[(5,​6-​diphenylpyrazinyl)(1-​methylethyl)amino]butoxy]-​acetic acid
CAS Number 475085-57-5
Molecular Formula C25H29N3O3
Formula Weight 419.5
Formulation A crystalline solid
Purity ≥98%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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OC(=O)​COCCCCN(C(C)​C)​c1cnc(c2ccccc2)​c(n1)​c1ccccc1

Background Reading

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).

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).

Cui, Y., Kataoka, Y., Satoh, T., et al. Protective effect of prostaglandin I2 analogs on ischemic delayed neuronal damage in gerbils. Biochem Biophys Res Commun 265 301-304 (1999).

Cheng, Y., Austin, S.C., Rocca, B., et al. Role of prostacyclin in the cardiovascular response to thromboxane A2. Science 296 539-541 (2002).

McLaughlin, V.V., Genthner, D.E., Panella, M.M., et al. Reduction in pulmonary vascular resistance with long-term epoprostenol (prostacyclin) therapy in primary pulmonary hypertension. N Engl J Med 338 273-277 (1998).

Murata, T., Ushikubi, F., Matsuoka, T., et al. Altered pain perception and inflammatory response in mice lacking prostacyclin receptor. Nature 388 678-682 (1997).

Aristoff, P.A., Johnson, P.D., and Harrison, A.W. Synthesis of 9-substituted carbacyclin analogues. J Org Chem 48 5341-5348 (1983).

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Size Price Quantity Subtotal
1 mg $36.00 $0.00
5 mg $162.00 $0.00
10 mg $288.00 $0.00
50 mg $1,260.00 $0.00
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Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

16(R)-AFP 07 (free acid) Exclusive
Beraprost (sodium salt)
Carbaprostacyclin
Iloprost
NS-304
Prostaglandin I2 (sodium salt)
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