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    Chemistry

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    Also known as: 475086-01-2, Ns-304, Uptravi, Act-293987, Ns 304, Act 293987
    Molecular Formula
    C26H32N4O4S
    Molecular Weight
    496.6  g/mol
    InChI Key
    QXWZQTURMXZVHJ-UHFFFAOYSA-N
    FDA UNII
    5EXC0E384L
    Selexipag
    Selexipag was approved by the United States FDA on December 22, 2015 for the treatment of pulmonary arterial hypertension (PAH) to delay disease progression and reduce risk of hospitalization. PAH is a relatively rare disease with usually a poor prognosis requiring more treatment options to prolong long-term outcomes. Marketed by Actelion Pharmaceuticals under brand name Uptravi, selexipag and its active metabolite, ACT-333679 (MRE-269), act as agonists of the prostacyclin receptor to increase vasodilation in the pulmonary circulation and decrease elevated pressure in the blood vessels supplying blood to the lungs.
    Selexipag is a Prostacyclin Receptor Agonist. The mechanism of action of selexipag is as a Prostacyclin Receptor Agonist.
    1 2D Structure

    Selexipag

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[4-[(5,6-diphenylpyrazin-2-yl)-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide
    2.1.2 InChI
    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)
    2.1.3 InChI Key
    QXWZQTURMXZVHJ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)N(CCCCOCC(=O)NS(=O)(=O)C)C1=CN=C(C(=N1)C2=CC=CC=C2)C3=CC=CC=C3
    2.2 Other Identifiers
    2.2.1 UNII
    5EXC0E384L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)-n-(methylsulfonyl)acetamide

    2. Act 293987

    3. Act-293987

    4. Act293987

    5. Ns-304

    6. Uptravi

    2.3.2 Depositor-Supplied Synonyms

    1. 475086-01-2

    2. Ns-304

    3. Uptravi

    4. Act-293987

    5. Ns 304

    6. Act 293987

    7. 2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)-n-(methylsulfonyl)acetamide

    8. 5exc0e384l

    9. 2-[4-[(5,6-diphenylpyrazin-2-yl)-propan-2-ylamino]butoxy]-n-methylsulfonylacetamide

    10. Ns-304;act-293987

    11. 2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}-n-(methanesulfonyl)acetamide

    12. 2-(4-((5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino)butoxy}-n-(methanesulfonyl)acetamide

    13. 2-[4-[(5,6-diphenyl-2-pyrazinyl)(1-methylethyl)amino]butoxy]-n-(methylsulfonyl)acetamide

    14. Unii-5exc0e384l

    15. Selexipag [usan:inn]

    16. 2-(4-((5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino)butoxy)-n-(methanesulfonyl)acetamide

    17. Uptravi (tn)

    18. Act293987

    19. Ns-304(selexipag)

    20. Selexipag(ns-304)

    21. Selexipag [inn]

    22. Selexipag [jan]

    23. Selexipag [mi]

    24. Selexipag [usan]

    25. Selexipag [who-dd]

    26. Selexipag (jan/usan/inn)

    27. Schembl674122

    28. Chembl238804

    29. Gtpl7552

    30. Selexipag [orange Book]

    31. Chebi:90844

    32. Dtxsid301027959

    33. Amy10851

    34. Bcp09146

    35. Zinc3990451

    36. Bdbm50235383

    37. Mfcd10567093

    38. S3726

    39. Akos024457572

    40. Ccg-269668

    41. Cs-3774

    42. Db11362

    43. Sb17055

    44. 2-{4-[n-(5,6-diphenylpyrazin-2-yl)-n-isopropylamino]butyloxy}-n-(methylsulfonyl)acetamide

    45. Ncgc00370833-01

    46. Ncgc00370833-02

    47. Ac-30209

    48. Bs-16872

    49. Hy-14870

    50. Db-119997

    51. B7378

    52. Ft-0776043

    53. D09994

    54. A857156

    55. Q15424759

    56. 2-(4-((5,6-diphenyl-2-pyrazinyl)(isopropyl)amino)butoxy)-n-(methylsulfonyl)acetamide

    57. 2-[4-[[5,6-di(phenyl)pyrazin-2-yl]-propan-2-ylamino]butoxy]-n-methylsulfonylacetamide

    58. 2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}-n-methanesulfonylacetamide

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 496.6 g/mol
    Molecular Formula C26H32N4O4S
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count12
    Exact Mass496.21442669 g/mol
    Monoisotopic Mass496.21442669 g/mol
    Topological Polar Surface Area110 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity730
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Selexipag is indicated for the treatment of pulmonary arterial hypertension (PAH) to delay disease progression and reduce risk of hospitalization.

    FDA Label

    Uptravi is indicated for the long-term treatment of pulmonary arterial hypertension (PAH) in adult patients with WHO functional class (FC) IIIII, either as combination therapy in patients insufficiently controlled with an endothelin receptor antagonist (ERA) and/or a phosphodiesterase type 5 (PDE-5) inhibitor, or as monotherapy in patients who are not candidates for these therapies.

    Efficacy has been shown in a PAH population including idiopathic and heritable PAH, PAH associated with connective tissue disorders, and PAH associated with corrected simple congenital heart disease.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    At the maximum tolerated dose of 1600 mcg twice per day, selexipag was not found to prolong the QT interval to a clinically relevant extent. Both selexipag and its metabolite caused concentration-dependent inhibition of platelet aggregation in vitro with IC50 of 5.5 M and 0.21 M, respectively. However, at clinically relevant concentrations, there was no effect on platelet aggregation test parameters following multiple dose administration of selexipag in healthy patients.

    5.2 MeSH Pharmacological Classification

    Antihypertensive Agents

    Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    SELEXIPAG
    5.3.2 FDA UNII
    5EXC0E384L
    5.3.3 Pharmacological Classes
    Prostacyclin Receptor Agonists [MoA]; Prostacyclin Receptor Agonist [EPC]
    5.4 ATC Code

    B01AC27

    B - Blood and blood forming organs

    B01 - Antithrombotic agents

    B01A - Antithrombotic agents

    B01AC - Platelet aggregation inhibitors excl. heparin

    B01AC27 - Selexipag

    5.5 Absorption, Distribution and Excretion

    Absorption

    After oral administration, maximum concentrations of selexipag and its metabolite were observed to be reached at 1-3 and 3-4 hours, respectively. Absorption was impaired in the presence of food, resulting in delayed time to maximum concentration as well as ~30% lower peak plasma concentration. However, exposure was not found to be significantly affected by food.

    Route of Elimination

    93% in feces, 12% in urine.

    Clearance

    On average, 35 L/hour.

    5.6 Metabolism/Metabolites

    Selexipag yields its active metabolite by hydrolysis of the acylsulfonamide by the enzyme hepatic carboxylesterase 1. Oxidative metabolism catalyzed by CYP3A4 and CYP2C8 results in hydroxylated and dealkylated products. UGT1A3 and UGT2B7 are involved in the glucuronidation of the active metabolite. Other than active metabolite, other metabolites in circulation do not exceed 3% of the total drug-related material.

    5.7 Biological Half-Life

    Selexipag's terminal half life is 0.8-2.5 hours. The active metabolite's terminal half life is 6.2-13.5 hours.

    5.8 Mechanism of Action

    Selexipag is a selective prostacyclin (IP, also called PGI2) receptor agonist. The key features of pulmonary arterial hypertension include a decrease in prostacyclin and prostacyclin synthase (enzyme that helps produce prostacyclin) in the lung. Prostacyclin is a potent vasodilator with anti-proliferative, anti-inflammatory, and anti-thrombotic effects; therefore, there is strong rationale for treatment with IP receptor agonists. Selexipag is chemically distinct as it is not PGI2 or a PGI2 analogue and has high selectivity for the IP receptor. It is metabolized by carboxylesterase 1 to yield an active metabolite (ACT-333679) that is approximately 37 times more potent than selexipag. Both selexipag and its metabolite are selective for the IP receptor over other prostanoid receptors.

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    23-Dec-2021
    22-Apr-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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