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    Chemistry

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    Also known as: 147536-97-8, Tracleer, Actelion, Bosentan anhydrous, Ro 47-0203, Ro-47-0203
    Molecular Formula
    C27H29N5O6S
    Molecular Weight
    551.6  g/mol
    InChI Key
    GJPICJJJRGTNOD-UHFFFAOYSA-N
    FDA UNII
    XUL93R30K2
    Bosentan Hydrate
    A sulfonamide and pyrimidine derivative that acts as a dual endothelin receptor antagonist used to manage PULMONARY HYPERTENSION and SYSTEMIC SCLEROSIS.
    Bosentan anhydrous is an Endothelin Receptor Antagonist. The mechanism of action of bosentan anhydrous is as an Endothelin Receptor Antagonist, and Cytochrome P450 3A Inducer, and Cytochrome P450 2C9 Inducer.
    1 2D Structure

    Bosentan Hydrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide
    2.1.2 InChI
    InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32)
    2.1.3 InChI Key
    GJPICJJJRGTNOD-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC2=C(C(=NC(=N2)C3=NC=CC=N3)OCCO)OC4=CC=CC=C4OC
    2.2 Other Identifiers
    2.2.1 UNII
    XUL93R30K2
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-t-butyl-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide

    2. Bosentan Anhydrous

    3. Bosentan Monohydrate

    4. Ro 47 0203

    5. Ro 47-0203

    6. Ro 470203

    7. Ro-47-0203

    8. Tracleer

    2.3.2 Depositor-Supplied Synonyms

    1. 147536-97-8

    2. Tracleer

    3. Actelion

    4. Bosentan Anhydrous

    5. Ro 47-0203

    6. Ro-47-0203

    7. Anhydrous Bosentan

    8. Bosentan [usan:inn:ban]

    9. 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide

    10. P-tert-butyl-n-(6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulfonamide

    11. Bosentan (inn)

    12. 4-(tert-butyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2'-bipyrimidin]-4-yl)benzenesulfonamide

    13. Chembl957

    14. Xul93r30k2

    15. N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide

    16. Chebi:51450

    17. 147536-97-8 (free)

    18. 174227-18-0

    19. Benzenesulfonamide, 4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)(2,2'-bipyrimidin)-4-yl)-

    20. Ncgc00167440-01

    21. Bosentan [inn]

    22. Dsstox_cid_26627

    23. Dsstox_rid_81776

    24. Dsstox_gsid_46627

    25. 1174918-31-0

    26. 4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) Benzenesulfornamide

    27. 4-tert-butyl-n-[6-(2-hydroxyethyloxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]benzenesulfonamide

    28. Benzenesulfonamide, 4-(1,1-dimethylethyl)-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-

    29. Bosentanum

    30. Ro-47-0203/029

    31. 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl]benzenesulfonamide

    32. Cas-147536-97-8

    33. Ro 47-0203/039

    34. Sr-05000001532

    35. Ro-470203029

    36. Ro-47-0203-029

    37. Unii-xul93r30k2

    38. 4-tert-butyl-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide

    39. 4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl)benzenesulfornamide

    40. Ks-5062

    41. Starbld0043886

    42. Bosentan [mi]

    43. Ro-47-0203/039

    44. Bosentan [who-dd]

    45. Schembl4218

    46. Gtpl3494

    47. Dtxsid7046627

    48. Hms2090n14

    49. Hms3652f15

    50. Hms3715n05

    51. Hms3750a13

    52. Bcp05202

    53. Hy-a0013

    54. Zinc1538857

    55. Tox21_112444

    56. Ac-148

    57. Bdbm50061101

    58. Pdsp1_001731

    59. Pdsp2_001714

    60. S4220

    61. Akos015852063

    62. Tox21_112444_1

    63. Am84442

    64. Bcp9000445

    65. Ccg-221182

    66. Cs-0381

    67. Db00559

    68. Sb17356

    69. Ncgc00167440-02

    70. Bb164259

    71. B5118

    72. Ft-0658809

    73. Sw199648-3

    74. D07538

    75. W18800

    76. Ab01275536-01

    77. 212b550

    78. A808658

    79. L001086

    80. Q419769

    81. J-008366

    82. Sr-05000001532-1

    83. Sr-05000001532-2

    84. Sr-05000001532-4

    85. Z1541632805

    86. 4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2''-bipyrimidin)-4-yl) Benzenesulfornamide

    87. 4-(1,1-dimethylethyl)-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzenesulfonamide

    88. 4-(tert-butyl)-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzenesulfonamide

    89. 4-tert Butyl-n-[4-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)pyrimidin-6-yl]benzenesulphonamide

    90. 4-tert-butyl-n-[6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-benzenesulfonamide

    91. 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2'-bipyrimidine]-4-yl]benzene-1-sulfonamide

    92. 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2''-bipyrimidin-4-yl]benzenesulfonamide

    93. 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide

    94. 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide

    95. 4-tert-butyl-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzenesulfonamide

    96. K86

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 551.6 g/mol
    Molecular Formula C27H29N5O6S
    XLogP33.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count11
    Exact Mass551.18385484 g/mol
    Monoisotopic Mass551.18385484 g/mol
    Topological Polar Surface Area154 Ų
    Heavy Atom Count39
    Formal Charge0
    Complexity839
    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 NameTracleer
    PubMed HealthBosentan (By mouth)
    Drug ClassesAntihypertensive
    Drug LabelTracleer is the proprietary name for bosentan, an endothelin receptor antagonist that belongs to a class of highly substituted pyrimidine derivatives, with no chiral centers. It is designated chemically as 4-tert-butyl-N-[6-(2-hydroxy-ethoxy)-5-(2-me...
    Active IngredientBosentan
    Dosage FormTablet
    RouteOral
    Strength125mg; 62.5mg
    Market StatusPrescription
    CompanyActelion Pharms

    2 of 2  
    Drug NameTracleer
    PubMed HealthBosentan (By mouth)
    Drug ClassesAntihypertensive
    Drug LabelTracleer is the proprietary name for bosentan, an endothelin receptor antagonist that belongs to a class of highly substituted pyrimidine derivatives, with no chiral centers. It is designated chemically as 4-tert-butyl-N-[6-(2-hydroxy-ethoxy)-5-(2-me...
    Active IngredientBosentan
    Dosage FormTablet
    RouteOral
    Strength125mg; 62.5mg
    Market StatusPrescription
    CompanyActelion Pharms

    4.2 Drug Indication

    Used in the treatment of pulmonary arterial hypertension (PAH), to improve exercise ability and to decrease the rate of clinical worsening (in patients with WHO Class III or IV symptoms).

    FDA Label

    Treatment of pulmonary arterial hypertension (PAH) to improve exercise capacity and symptoms in patients with WHO functional class III. Efficacy has been shown in:

    - Primary (idiopathic and familial) PAH;

    - PAH secondary to scleroderma without significant interstitial pulmonary disease;

    - PAH associated with congenital systemic-to-pulmonary shunts and Eisenmenger's physiology.

    Some improvements have also been shown in patients with PAH WHO functional class II.

    Tracleer is also indicated to reduce the number of new digital ulcers in patients with systemic sclerosis and ongoing digital ulcer disease.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Bosentan belongs to a class of drugs known as endothelin receptor antagonists (ERAs). Patients with PAH have elevated levels of endothelin, a potent blood vessel constrictor, in their plasma and lung tissue. Bosentan blocks the binding of endothelin to its receptors, thereby negating endothelin's deleterious effects.

    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.)

    Endothelin Receptor Antagonists

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

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    BOSENTAN ANHYDROUS
    5.3.2 FDA UNII
    XUL93R30K2
    5.3.3 Pharmacological Classes
    Cytochrome P450 3A Inducers [MoA]; Endothelin Receptor Antagonist [EPC]; Endothelin Receptor Antagonists [MoA]; Cytochrome P450 2C9 Inducers [MoA]
    5.4 ATC Code

    C02KX01

    C02KX01

    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

    C02KX01 - Bosentan

    5.5 Absorption, Distribution and Excretion

    Absorption

    Absolute bioavailability is approximately 50% and food does not affect absorption.

    Route of Elimination

    Bosentan is eliminated by biliary excretion following metabolism in the liver.

    Volume of Distribution

    18 L

    Clearance

    4 L/h [patients with pulmonary arterial hypertension]

    5.6 Metabolism/Metabolites

    Bosentan is metabolized in the liver by the cytochrome P450 enzymes CYP2C9 and CYP3A4 (and possibly CYP2C19), producing three metabolites, one of which, Ro 48-5033, is pharmacologically active and may contribute 10 to 20% to the total activity of the parent compound.

    Bosentan has known human metabolites that include 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-[2,2-]bipyrimidinyl-4-yl]-benzenesulfonamide and Hydroxy Bosentan.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Terminal elimination half-life is about 5 hours in healthy adult subjects.

    5.8 Mechanism of Action

    Endothelin-1 (ET-1) is a neurohormone, the effects of which are mediated by binding to ETA and ETB receptors in the endothelium and vascular smooth muscle. It displays a slightly higher affinity towards ETA receptors than ETB receptors. ET-1 concentrations are elevated in plasma and lung tissue of patients with pulmonary arterial hypertension, suggesting a pathogenic role for ET-1 in this disease. Bosentan is a specific and competitive antagonist at endothelin receptor types ETA and ETB.

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    07-Jan-2021
    22-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - TABLET;ORAL - 125MG

    USFDA APPLICATION NUMBER - 21290

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    DOSAGE - TABLET;ORAL - 62.5MG

    USFDA APPLICATION NUMBER - 21290

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