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    Also known as: 441798-33-0, Opsumit, Act-064992, Act 064992, N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-n'-propylsulfamide, Act064992
    Molecular Formula
    C19H20Br2N6O4S
    Molecular Weight
    588.3  g/mol
    InChI Key
    JGCMEBMXRHSZKX-UHFFFAOYSA-N
    FDA UNII
    Z9K9Y9WMVL
    Macitentan
    Macitentan is an orally available dual endothelin receptor (ETR) antagonist with potential antihypertensive and antineoplastic activity. Upon administration, macitentan and its metabolites block the binding of endothelin isoform 1 (ET-1) to type-A and type-B ETR on both the tumor cells and the endothelial cells in the tumor vasculature. This prevents ET-1 mediated signaling transduction which may decrease tumor cell proliferation, progression, and angiogenesis in tumor tissue. ET-1, a potent vasoconstrictor that plays an important role in inflammation and tissue repair, is, together with its receptors, overexpressed varyingly in many tumor cell types.
    Macitentan is an Endothelin Receptor Antagonist. The mechanism of action of macitentan is as an Endothelin Receptor Antagonist.
    1 2D Structure

    Macitentan

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-N-(propylsulfamoyl)pyrimidin-4-amine
    2.1.2 InChI
    InChI=1S/C19H20Br2N6O4S/c1-2-7-26-32(28,29)27-17-16(13-3-5-14(20)6-4-13)18(25-12-24-17)30-8-9-31-19-22-10-15(21)11-23-19/h3-6,10-12,26H,2,7-9H2,1H3,(H,24,25,27)
    2.1.3 InChI Key
    JGCMEBMXRHSZKX-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCNS(=O)(=O)NC1=C(C(=NC=N1)OCCOC2=NC=C(C=N2)Br)C3=CC=C(C=C3)Br
    2.2 Other Identifiers
    2.2.1 UNII
    Z9K9Y9WMVL
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Act 064992

    2. Act-064992

    3. Act064992

    4. Actelion-1

    5. N-(5-(4-bromophenyl)-6-(2-(5-bromopyrimidin-2-yloxy)ethoxy)pyrimidin-4-yl)-n'-propylaminosulfonamide

    6. Opsumit

    2.3.2 Depositor-Supplied Synonyms

    1. 441798-33-0

    2. Opsumit

    3. Act-064992

    4. Act 064992

    5. N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-n'-propylsulfamide

    6. Act064992

    7. Z9k9y9wmvl

    8. 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-n-(propylsulfamoyl)pyrimidin-4-amine

    9. N-(5-(4-bromophenyl)-6-(2-((5-bromo-2-pyrimidinyl)oxy)ethoxy)-4-pyrimidinyl)-n'-propylsulfamide

    10. Chebi:76607

    11. Actelion-1

    12. Macitentan [inn]

    13. N-(5-(4-bromophenyl)-6-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)pyrimidin-4-yl)-n'-propylsulfamide

    14. N-[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]-n'- Propylsulfamide

    15. Macitentan [usan:inn]

    16. Unii-z9k9y9wmvl

    17. Macitentanum

    18. Sulfamide, N-(5-(4-bromophenyl)-6-(2-((5-bromo-2-pyrimidinyl)oxy)ethoxy)-4-pyrimidinyl)-n'-propyl-

    19. Sulfamide, N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-n'-propyl-

    20. Macitentan- Bio-x

    21. Opsumit (tn)

    22. Macitentan [mi]

    23. Macitentan [jan]

    24. Macitentan (jan/usan)

    25. Macitentan [usan]

    26. Macitentan [vandf]

    27. (non-labelled)macitentan-d7

    28. Macitentan [who-dd]

    29. Mls006011174

    30. Gtpl7352

    31. Schembl1445625

    32. Chembl2103873

    33. Macitentan [orange Book]

    34. Dtxsid50196063

    35. Ex-a544

    36. Hms3653n06

    37. Hms3747e09

    38. Cas:441798-33-0;macitentan

    39. Bcp05309

    40. Bdbm50395626

    41. Mfcd17167076

    42. S8051

    43. Zinc43202140

    44. Akos024463406

    45. Am81244

    46. Ccg-270155

    47. Cs-0686

    48. Db08932

    49. Sb14841

    50. Macitentan (actelion-1,act-064992)

    51. Ncgc00346456-01

    52. Ncgc00346456-05

    53. Ac-30102

    54. As-74590

    55. Bm162771

    56. Hy-14184

    57. N-(5-(4-bromophenyl)-6-(2-(5-bromopyrimidin-2-yloxy)ethoxy)pyrimidin-4-yl)-n'-propylaminosulfonamide

    58. Smr004702943

    59. Db-070519

    60. Ft-0696675

    61. Sw219473-1

    62. Act 064992; Act-064992

    63. D10135

    64. Q6724151

    65. {[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]sulfamoyl}(propyl)amine

    66. N-(5-(4-bromophenyl)-6-(2-((5-bromopyrimidin-2-yl)oxi)ethoxy)pyrimidin-4-yl)-n'-propylsulfuric Diamide

    67. N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)-oxy]ethoxy]-4-pyrimidinyl]-n'-propylsulfamide

    68. N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-n'-propyl-sulfamide

    69. N-[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]-n'-propylsulfuric Diamide

    2.4 Create Date
    2007-04-02
    3 Chemical and Physical Properties
    Molecular Weight 588.3 g/mol
    Molecular Formula C19H20Br2N6O4S
    XLogP33.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count11
    Exact Mass587.96130 g/mol
    Monoisotopic Mass585.96335 g/mol
    Topological Polar Surface Area137 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity642
    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 Information
    1 of 2  
    Drug NameOpsumit
    PubMed HealthMacitentan (By mouth)
    Drug ClassesAntihypertensive
    Drug LabelOPSUMIT (macitentan) is an endothelin receptor antagonist. The chemical name of macitentan is N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide. It has a molecular formula of C19H20Br2N6O4S and a molecula
    Active IngredientMacitentan
    Dosage FormTablet
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyActelion Pharms

    2 of 2  
    Drug NameOpsumit
    PubMed HealthMacitentan (By mouth)
    Drug ClassesAntihypertensive
    Drug LabelOPSUMIT (macitentan) is an endothelin receptor antagonist. The chemical name of macitentan is N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide. It has a molecular formula of C19H20Br2N6O4S and a molecula
    Active IngredientMacitentan
    Dosage FormTablet
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyActelion Pharms

    4.2 Drug Indication

    Investigated for use/treatment in cardiovascular disorders, hypertension, and pulmonary hypertension.

    Macitentan is indicated for the treatment of WHO group 1 pulmonary arterial hypertension (PAH) both alone and in combination with tadalafil.

    FDA Label

    Opsumit, as monotherapy or in combination, is indicated for the long-term treatment of pulmonary arterial hypertension (PAH) in adult patients of WHO Functional Class (FC) II to III.

    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.

    Treatment of chronic thromboembolic pulmonary hypertension (CTEPH)

    Treatment of idiopathic pulmonary fibrosis, Treatment of pulmonary arterial hypertension, Treatment of systemic sclerosis

    Treatment of functional single ventricle heart disease with total cavo-pulmonary connection

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Macitentan acts primarily by reducing vasoconstriction and cell proliferation due to endothelin overexpression.

    5.2 MeSH Pharmacological Classification

    Endothelin A Receptor Antagonists

    Compounds and drugs that bind to and inhibit or block the activation of ENDOTHELIN A RECECPTORS. (See all compounds classified as Endothelin A Receptor Antagonists.)

    Endothelin B Receptor Antagonists

    Compounds and drugs that bind to and inhibit or block the activation of ENDOTHELIN B RECEPTORS. (See all compounds classified as Endothelin B Receptor Antagonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    MACITENTAN
    5.3.2 FDA UNII
    Z9K9Y9WMVL
    5.3.3 Pharmacological Classes
    Endothelin Receptor Antagonists [MoA]; Endothelin Receptor Antagonist [EPC]
    5.4 ATC Code

    C02KX04

    C02KX04

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    C - Cardiovascular system

    C02 - Antihypertensives

    C02K - Other antihypertensives

    C02KX - Antihypertensives for pulmonary arterial hypertension

    C02KX04 - Macitentan

    5.5 Absorption, Distribution and Excretion

    Absorption

    Macitentan has a median Tmax of 8h although some studies have found up to 30h at higher doses. Although the bioavailability has not been experimentally determined, pharmacokinetic modeling has estimated it at 74%. Food has not been found to have a significant effect on absorption.

    Route of Elimination

    Eliminated 50% through urine and 24% through feces. Of the 50% excreted through the urine, none of the recovered dose was in the form of the parent drug nor the active metabolite.

    Volume of Distribution

    Macitentan has an apparent volume of distribution of 40-50L.

    Clearance

    Clearance data was not found.

    5.6 Metabolism/Metabolites

    Macitentan undergoes oxidative depropylation of the sulfonamide moiety via CYP3A4, 2C8, 2C9, and 2C19 to form the active metabolite M6. The ethylene glycol moiety undergoes oxidative cleavage via CYP2C9 to the alcohol metabolite M4. M4 is oxidized to its corresponding acid, M5, then hydrolyzed to the metabolite termed m/z 324. Oxidative depropylation of a distal carbon atom via CYP2C8, 2C9, and 2C19 forms M7. Hydrolysis of both macitentan and M5 produces M3. Finally M5 may be further metabolized via hydrolysis and hydroxylation to M2 or via glucuronidation to a glucuronide metabolite, M1.

    5.7 Biological Half-Life

    The half-life of elimination of macitentan is 16 hours. The half-life of elimination of the active metabolite is 40-66h

    5.8 Mechanism of Action

    Through complete blockade of tissular endothelin, Actelion-1 is expected to protect tissue from the damaging effect of elevated endothelin, specifically in the cardiovascular system. In pre-clinical studies, Actelion-1 also exhibited effects suggesting that it maintains the integrity of the vascular wall and improves long-term outcome. Accordingly, Actelion-1 may provide therapeutic benefit in a wide range of cardiovascular indications.

    Macitentan is an antagonist which binds to the endothelin A and B receptors (EA and EB) and blocks signaling from endothelin-1 and -2. Pulmonary arterial hypertension has many different mechanisms which contribute to the development of endothelial dysfunction including elevated cytosolic calcium, genetic factors, epigenetic changes, and mitochondrial dysfunction. The focus of macitentan's mechanism relates to the role of overexpressed endothelin from the vascular endothelium. Endothelins are released in both a constitutive fashion from secretory vesicles and in response to stimuli via Weibel-Palade storage granules. Endothelins bind to the EA and EB receptors, with endothelins -1 and -2 having more affinity than endothelin-3. Binding to the Gq coupled EA receptor triggers Ca2+ release from the sarcoplasmic reticulum of smooth muscle cells via the phospholipase C (PLC) pathway. Downstream protein kinase C activation may also contribute to increased Ca2+ sensitivity of the contractile apparatus. EA receptor activation is also known to contribute to pulmonary artery smooth muscle cell proliferation. The binding of endothelins to the EB receptors acts in opposition to EA signaling by activating the same PLC cascade in endothelial cells to activate endothelial nitric oxide synthase. The subsequent release of nitric oxide produces vasodilation through the cyclic guanosine monophosphate cascade. Despite the greater presence of EB receptors on endothelial cells, they are still present on smooth muscle cells and may contribute to cell proliferation through the same mechanisms as EA receptors. Macitentan is thought to provide its therapeutic effect primarily via blocking signaling through EA which produces both decreased vasoconstriction via reduced smooth muscle cell contractility and attenuation of the hyperproliferation of smooth muscle cells found in PAH. Blockade of EB is less likely to contribute to a therapeutic effect as this signaling is responsible for the counter-regulatory vasodilatory signal.

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    16-Jan-2021
    05-Aug-2024
    KGS
    overview
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    Average Price (USD/KGS)

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

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    (USD/KGS)    		 Number of Transactions

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