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MedKoo Cat#: 317125 | Name: Selexipag
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Selexipag, also known as ACT-293987 and NS-304, is a a first-in-class orally available selective non-prostanoid IP receptor agonist, which is currently in development by Actelion as a treatment of pulmonary arterial hypertension. Selexipag and its active metabolite, ACT-333679, are agonists at the prostacyclin receptor, which leads to vasodilation in the pulmonary circulation.

Chemical Structure

Selexipag
Selexipag
CAS#475086-01-2

Theoretical Analysis

MedKoo Cat#: 317125

Name: Selexipag

CAS#: 475086-01-2

Chemical Formula: C26H32N4O4S

Exact Mass: 496.2144

Molecular Weight: 496.62

Elemental Analysis: C, 62.88; H, 6.50; N, 11.28; O, 12.89; S, 6.46

Price and Availability

Size Price Availability Quantity
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 950.00 Ready to ship
1g USD 1,650.00 Ready to ship
2g USD 2,950.00 Ready to ship
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Related CAS #
No Data
Synonym
NS-304; NS304; NS 304; ACT-293987; ACT293987; ACT 293987; Selexipag; Uptravi.
IUPAC/Chemical Name
2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}-N-(methanesulfonyl)acetamide
InChi Key
QXWZQTURMXZVHJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C26H32N4O4S/c1-20(2)30(16-10-11-17-34-19-24(31)29-35(3,32)33)23-18-27-25(21-12-6-4-7-13-21)26(28-23)22-14-8-5-9-15-22/h4-9,12-15,18,20H,10-11,16-17,19H2,1-3H3,(H,29,31)
SMILES Code
CC(N(CCCCOCC(NS(C)(=O)=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
More Info
Biological target:
Selexipag (NS-304) is an agonist for the Prostacyclin (PGI2) receptor (IP receptor) with Ki of 260 nM.
In vitro activity:
Prostacyclin (PGI2) receptor (IP receptor) agonists, which are indicated for the treatment of pulmonary arterial hypertension (PAH), increase cytosolic cAMP levels and thereby inhibit pulmonary vasoconstriction, pulmonary arterial smooth muscle cell (PASMC) proliferation, and extracellular matrix synthesis. Selexipag is an IP receptor agonist. The active metabolite of selexipag, ACT-333679, behaved as a full agonist in multiple PAH-relevant receptor-distal-or downstream-cellular assays with a maximal efficacy (Emax) comparable to that of the prototypic PGI2 analog iloprost. In PASMC, ACT-333679 potently induced cellular relaxation (EC50 4.3 nM) and inhibited cell proliferation (IC50 4.0 nM) as well as extracellular matrix synthesis (IC50 8.3 nM). In contrast, ACT-333679 displayed partial agonism in receptor-proximal-or upstream-cAMP accumulation assays (Emax 56%) when compared with iloprost and the PGI2 analogs beraprost and treprostinil (Emax ∼100%). Partial agonism of ACT-333679 also resulted in limited β-arrestin recruitment (Emax 40%) and lack of sustained IP receptor internalization, whereas all tested PGI2 analogs behaved as full agonists in these desensitization-related assays. Reference: J Pharmacol Exp Ther. 2017 Jul;362(1):186-199. https://jpet.aspetjournals.org/content/362/1/186.long
In vivo activity:
Selexipag is a novel prostacyclin receptor (IP receptor) agonist approved for the treatment of pulmonary arterial hypertension (PAH). Selexipag is converted to MRE-269 in vivo, and the plasma concentration of MRE-269 is maintained at a therapeutic level for a long time. MRE-269 has selective IP receptor agonist activity and exerts vasodilatory and anti-proliferative effects on pulmonary arterial smooth muscle cells. In a Sugen 5416/hypoxia rat model of PAH, selexipag significantly improved pulmonary artery obstruction, decreased right ventricular systolic pressure, decreased right ventricular hypertrophy and improved survival rate. Reference: Nihon Yakurigaku Zasshi. 2021;156(3):178-186. https://www.jstage.jst.go.jp/article/fpj/156/3/156_20092/_article/-char/ja/
Solvent mg/mL mM
Solubility
DMSO 57.2 115.12
Ethanol 34.5 69.47
DMF 30.0 60.41
PBS (pH 7.2) 1.0 2.01
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 496.62 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
Formulation protocol:
1. Gatfield J, Menyhart K, Wanner D, Gnerre C, Monnier L, Morrison K, Hess P, Iglarz M, Clozel M, Nayler O. Selexipag Active Metabolite ACT-333679 Displays Strong Anticontractile and Antiremodeling Effects but Low β-Arrestin Recruitment and Desensitization Potential. J Pharmacol Exp Ther. 2017 Jul;362(1):186-199. doi: 10.1124/jpet.116.239665. Epub 2017 May 5. PMID: 28476928. 2. Kuwano K, Kosugi K, Fuchikami C, Funaki S. [Pharmacological characteristics and clinical study results of Selexipag (Uptravi® tablets), a selective prostacyclin receptor agonist]. Nihon Yakurigaku Zasshi. 2021;156(3):178-186. Japanese. doi: 10.1254/fpj.20092. PMID: 33952848.
In vitro protocol:
1. Gatfield J, Menyhart K, Wanner D, Gnerre C, Monnier L, Morrison K, Hess P, Iglarz M, Clozel M, Nayler O. Selexipag Active Metabolite ACT-333679 Displays Strong Anticontractile and Antiremodeling Effects but Low β-Arrestin Recruitment and Desensitization Potential. J Pharmacol Exp Ther. 2017 Jul;362(1):186-199. doi: 10.1124/jpet.116.239665. Epub 2017 May 5. PMID: 28476928.
In vivo protocol:
1. Kuwano K, Kosugi K, Fuchikami C, Funaki S. [Pharmacological characteristics and clinical study results of Selexipag (Uptravi® tablets), a selective prostacyclin receptor agonist]. Nihon Yakurigaku Zasshi. 2021;156(3):178-186. Japanese. doi: 10.1254/fpj.20092. PMID: 33952848.
1: Sitbon O, Channick R, Chin KM, Frey A, Gaine S, Galiè N, Ghofrani HA, Hoeper MM, Lang IM, Preiss R, Rubin LJ, Di Scala L, Tapson V, Adzerikho I, Liu J, Moiseeva O, Zeng X, Simonneau G, McLaughlin VV; GRIPHON Investigators. Selexipag for the Treatment of Pulmonary Arterial Hypertension. N Engl J Med. 2015 Dec 24;373(26):2522-33. doi: 10.1056/NEJMoa1503184. PMID: 26699168. 2: Genecand L, Wacker J, Beghetti M, Lador F. Selexipag for the treatment of pulmonary arterial hypertension. Expert Rev Respir Med. 2021 May;15(5):583-595. doi: 10.1080/17476348.2021.1866990. Epub 2020 Dec 31. PMID: 33382345. 3: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Selexipag. 2016 Nov 10. PMID: 31644051. 4: Selexipag for pulmonary arterial hypertension. Aust Prescr. 2021 Apr;44(2):67-68. doi: 10.18773/austprescr.2021.007. Epub 2021 Feb 4. PMID: 33911339; PMCID: PMC8075744. 5: Panagiotidou E, Boutou A, Pitsiou G. An evaluation of selexipag for the treatment of pulmonary hypertension. Expert Opin Pharmacother. 2021 Jan;22(1):29-36. doi: 10.1080/14656566.2020.1812579. Epub 2020 Aug 31. PMID: 32867545. 6: Galiè N, Gaine S, Channick R, Coghlan JG, Hoeper MM, Lang IM, McLaughlin VV, Lassen C, Rubin LJ, Hsu Schmitz SF, Sitbon O, Tapson VF, Chin KM. Long-Term Survival, Safety and Tolerability with Selexipag in Patients with Pulmonary Arterial Hypertension: Results from GRIPHON and its Open-Label Extension. Adv Ther. 2022 Jan;39(1):796-810. doi: 10.1007/s12325-021-01898-1. Epub 2021 Oct 30. PMID: 34727317; PMCID: PMC8799580. 7: Noel ZR, Kido K, Macaulay TE. Selexipag for the treatment of pulmonary arterial hypertension. Am J Health Syst Pharm. 2017 Aug 1;74(15):1135-1141. doi: 10.2146/ajhp160798. Epub 2017 May 22. PMID: 28533253. 8: Li M, Liu L, Liu C, Chen Z, Li W, Li X, Ma X, Zhang Y. Selexipag for the Treatment of Pediatric Pulmonary Hypertension: A Systematic Review. Clin Ther. 2024 Jan;46(1):59-68. doi: 10.1016/j.clinthera.2023.09.026. Epub 2023 Nov 7. PMID: 37945502. 9: Duggan ST, Keam SJ, Burness CB. Selexipag: A Review in Pulmonary Arterial Hypertension. Am J Cardiovasc Drugs. 2017 Feb;17(1):73-80. doi: 10.1007/s40256-016-0209-9. PMID: 27988834. 10: 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. PMID: 24392948. 11: Baker WL, Darsaklis K, Singhvi A, Salerno EL. Selexipag, an Oral Prostacyclin-Receptor Agonist for Pulmonary Arterial Hypertension. Ann Pharmacother. 2017 Jun;51(6):488-495. doi: 10.1177/1060028017697424. Epub 2017 Feb 1. PMID: 28478717. 12: Maeder MT. Selexipag and the pulmonary hypertension continuum. Eur J Heart Fail. 2022 Jan;24(1):215-218. doi: 10.1002/ejhf.2387. Epub 2021 Dec 12. PMID: 34816552. 13: Qin J, Wang G, Han D. Selexipag in Patients With Pulmonary Hypertension: A Systematic Review and Meta-Analysis of Randomized Controlled Trials. Curr Probl Cardiol. 2023 Feb;48(2):101466. doi: 10.1016/j.cpcardiol.2022.101466. Epub 2022 Oct 23. PMID: 36283497. 14: Scott LJ. Selexipag: First Global Approval. Drugs. 2016 Mar;76(3):413-8. doi: 10.1007/s40265-016-0549-4. PMID: 26846322. 15: Rosenkranz S, Channick R, Chin KM, Jenner B, Gaine S, Galiè N, Ghofrani HA, Hoeper MM, McLaughlin VV, Du Roure C, Rubin LJ, Sitbon O, Tapson V, Lang IM. The impact of comorbidities on selexipag treatment effect in patients with pulmonary arterial hypertension: insights from the GRIPHON study. Eur J Heart Fail. 2022 Jan;24(1):205-214. doi: 10.1002/ejhf.2369. Epub 2021 Nov 21. Erratum in: Eur J Heart Fail. 2022 Aug;24(8):1453. doi: 10.1002/ejhf.2564. PMID: 34806261; PMCID: PMC9298818. 16: McLaughlin V, Farber HW, Highland KB, Hemnes AR, Chakinala MM, Chin KM, Han M, Cho M, Tobore T, Rahman M, Kim NH. Disease characteristics, treatments, and outcomes of patients with pulmonary arterial hypertension treated with selexipag in real-world settings from the SPHERE registry (SelexiPag: tHe usErs dRug rEgistry). J Heart Lung Transplant. 2024 Feb;43(2):272-283. doi: 10.1016/j.healun.2023.09.016. Epub 2023 Sep 29. PMID: 37778526. 17: Richter MJ, Gall H, Grimminger J, Grimminger F, Ghofrani HA. Selexipag for the treatment of pulmonary arterial hypertension. Expert Opin Pharmacother. 2016 Sep;17(13):1825-34. doi: 10.1080/14656566.2016.1215429. Epub 2016 Aug 2. PMID: 27467883. 18: Ogo T, Shimokawahara H, Kinoshita H, Sakao S, Abe K, Matoba S, Motoki H, Takama N, Ako J, Ikeda Y, Joho S, Maki H, Saeki T, Sugano T, Tsujino I, Yoshioka K, Shiota N, Tanaka S, Yamamoto C, Tanabe N, Tatsumi K; Study Group. Selexipag for the treatment of chronic thromboembolic pulmonary hypertension. Eur Respir J. 2022 Jul 7;60(1):2101694. doi: 10.1183/13993003.01694-2021. PMID: 34824052; PMCID: PMC9260121. 19: Ghosh RK, Ball S, Das A, Bandyopadhyay D, Mondal S, Saha D, Gupta A. Selexipag in Pulmonary Arterial Hypertension: Most Updated Evidence From Recent Preclinical and Clinical Studies. J Clin Pharmacol. 2017 May;57(5):547-557. doi: 10.1002/jcph.834. Epub 2016 Dec 21. PMID: 27670133. 20: Honorato Pérez J. Selexipag, a selective prostacyclin receptor agonist in pulmonary arterial hypertension: a pharmacology review. Expert Rev Clin Pharmacol. 2017 Jul;10(7):753-762. doi: 10.1080/17512433.2017.1322900. Epub 2017 May 19. PMID: 28524738.