ChemicalBook > CAS DataBase List > [4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID

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

Product Name
[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID
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;MRE-269, 10 mM in DMSO;Slapag metabolite ACT-333679;Selexipag metabolite ACT-333679;MRE-269 Selexipag Active Metabolite
CBNumber
CB22467360
Molecular Formula
C25H29N3O3
Formula Weight
419.52
MOL File
475085-57-5.mol
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[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID Property

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
InChIKey
OJQMKCBWYCWFPU-UHFFFAOYSA-N
SMILES
C(O)(=O)COCCCCN(C1=NC(C2=CC=CC=C2)=C(C2=CC=CC=C2)N=C1)C(C)C
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
10010412
Product name
MRE-269
Purity
≥98%
Packaging
1mg
Price
$36
Updated
2024/03/01
Cayman Chemical
Product number
10010412
Product name
MRE-269
Purity
≥98%
Packaging
5mg
Price
$87
Updated
2024/03/01
Cayman Chemical
Product number
10010412
Product name
MRE-269
Purity
≥98%
Packaging
10mg
Price
$155
Updated
2024/03/01
Cayman Chemical
Product number
10010412
Product name
MRE-269
Purity
≥98%
Packaging
50mg
Price
$510
Updated
2024/03/01
TRC
Product number
M750110
Product name
MRE-269
Packaging
10mg
Price
$120
Updated
2021/12/16
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[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID Chemical Properties,Usage,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.

in vivo

The vasorelaxant effects of MRE-269 on rat small intralobar pulmonary artery (SIPA) and EPA are the same, while the other IP receptor agonists induce less vasodilation in SIPA than in EPA[1]. MRE-269 produces substantial relaxation of rat small pulmonary artery, although its effects are only significant at high concentrations of above 10 μM (pEC50, 4.98±0.22). By contrast, in rat small pulmonary veins, MRE-269 only produces minimal relaxation over the whole concentration range, with only significant relaxation occurring at the two highest doses of MRE-269 of 10 and 100 μM[2].

IC 50

IP Receptor

References

[1] TAKAHIKO MURATA. Altered pain perception and inflammatory response in mice lacking prostacyclin receptor[J]. Nature, 1997, 388 6643: 678-682. DOI: 10.1038/41780
[2] YAN CHENG. Role of Prostacyclin in the Cardiovascular Response to Thromboxane A2[J]. Science, 2002, 296 5567. DOI: 10.1126/science.1068711
[3] YILONG CUI . Protective Effect of Prostaglandin I2 Analogs on Ischemic Delayed Neuronal Damage in Gerbils[J]. Biochemical and biophysical research communications, 1999, 265 2: Pages 301-304. DOI: 10.1006/bbrc.1999.1671
[4] V V MCLAUGHLIN. Reduction in pulmonary vascular resistance with long-term epoprostenol (prostacyclin) therapy in primary pulmonary hypertension.[J]. New England Journal of Medicine, 1998, 338 5: 273-277. DOI: 10.1056/nejm199801293380501
[5] KEIICHI KUWANO. 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]. Journal of Pharmacology and Experimental Therapeutics, 2007, 322 3: 1181-1188. DOI: 10.1124/jpet.107.124248
[6] KEIICHI KUWANO. 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]. Journal of Pharmacology and Experimental Therapeutics, 2008, 326 3: 691-699. DOI: 10.1124/jpet.108.138305
[7] NAOKI MATSUMOTO . The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms[J]. Prostaglandins & other lipid mediators, 2022, 162: Article 106662. DOI: 10.1016/j.prostaglandins.2022.106662

[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 Suppliers

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View Lastest Price from [4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID manufacturers

Moxin Chemicals
Product
Selexipag Impurity 475085-57-5
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
98
Supply Ability
10000000
Release date
2025-02-20
Shaanxi Dideu Medichem Co. Ltd
Product
[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID 475085-57-5
Price
US $0.10/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
1000Tons
Release date
2024-08-05
Henan Fengda Chemical Co., Ltd
Product
[4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID 475085-57-5
Price
US $35.00-0.90/kg
Min. Order
1kg
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-03-22

475085-57-5, [4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACIDRelated Search:

5-chloro-2,3-diphenylpyrazine ( 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butylester ) SELEXIPAG interMediate 2,3-DIPHENYLPYRAZINE Bromoacetic acid 2-T-BUTYL GLYCOLATE 4-(Isopropylamino)butanol 5,6-DIPHENYLPYRAZIN-2-OL N-(methylsulfonyl)glycine 2,3-Dichloro-5,6-diphenylpyrazine Pyrazinamide Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide Acetic acid, 2-[4-[(5,6-diphenyl-2-pyrazinyl)oxy]butoxy]- 2-Pyrazinamine, N-(1-methylethyl)-5,6-diphenyl- 1-Butanol, 4-[(5,6-diphenyl-2-pyrazinyl)oxy]- Acetic acid, 2-[4-[(5,6-diphenyl-2-pyrazinyl)oxy]butoxy]-, 1,1-dimethylethyl ester Acetamide, 2-[4-[(1-methylethyl)amino]butoxy]-N-(methylsulfonyl)- Acetamide, 2-[4-[(5,6-diphenyl-2-pyrazinyl)(1-methylethyl)amino]butoxy]-

  • [4-[(5,6-DIPHENYLPYRAZINYL)(1-METHYLETHYL)AMINO]BUTOXY]-ACETIC ACID
  • MRE-269
  • 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
  • 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
  • MRE-269, 10 mM in DMSO
  • Selexipag Metabolite (MRE-269, ACT-333679)
  • 475085-57-5