[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID

[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID Structure
CAS No.
475085-57-5
Chemical Name:
[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID
Synonyms
MRE-269;MRE-269 S;ACT 333679;MRE-269 (ACT-333679);Selexipag internate 2;MRE-269-d7 Sodium Salt;Slapag metabolite ACT-333679;Selexipag metabolite ACT-333679;MRE-269 Selexipag Active Metabolite;Selexipag metabolite (ACT 333679) D8
CBNumber:
CB22467360
Molecular Formula:
C25H29N3O3
Molecular Weight:
419.52
MOL File:
475085-57-5.mol
Modify Date:
2024/8/5 12:01:54

[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID Properties

Melting point 116 - 118°C
Boiling point 602.1±55.0 °C(Predicted)
Density 1.160
storage temp. Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka 3.51±0.10(Predicted)
form Solid
color Off-White to Light Yellow

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P280-P301+P312-P302+P352-P305+P351+P338
NFPA 704
0
2 0

[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID Chemical Properties,Uses,Production

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. The IP receptor also participates in signal transduction of the pain response, cardioprotection, and inflammation. 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. 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. Unlike the PGI2 analogues, beraprost and iloprost, MRE-269 lacks high affinity for the EP3 receptor. 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.

Uses

MRE-269 an orally available and long-acting prostacyclin receptor agonist prodrug. MRE-269 is used for the treatment of pulmonary arterial hypertension. MRE-269 is an active metabolite of Selexipag (S253150).

Definition

ChEBI: A member of the class of pyrazines that is {4-[(propan-2-yl)(pyrazin-2-yl)amino]butoxy}acetic acid carrying two additional phenyl substituents at positions 5 and 6 on the pyrazine ring. The active metabolite of selexipag, an orphan drug used for the treatm nt of pulmonary arterial hypertension.

[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID ACT 333679 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid Selexipag Active Metabolite (ACT-333679) {4-[(5,6-Diphenyl-2-pyrazinyl)(isopropyl)amino]butoxy}acetic acid MRE-269 (ACT-333679) MRE-269 Selexipag Active Metabolite MRE-269 S ACT-333679; MRE269; MRE 269; ACT333679; ACT 333679 Selexipag impurity 6/Selexipag Acid/2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}acetic acid Slapag metabolite ACT-333679 Selexipag metabolite ACT-333679 Acetic acid, 2-[4-[(5,6-diphenyl-2-pyrazinyl)(1-methylethyl)amino]butoxy]- 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)acetic acid {4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}acetic acid Selexipag internate 2 MRE-269-d7 Sodium Salt Selexipag metabolite (ACT 333679) D8 MRE-269 2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}acetic acid N-(3-chloro-4-methylphenyl)-2-[2-(3,4-dimethylphenyl)-3-oxo-1H,2H,3H-pyrazolo[3,4-b]pyridin-1-yl]acetamide 2-{4-[(5,6-Diphenylpyrazin-2-y2-{4-[(5,6-Diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}acetic acid 475085-57-5