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Bosentan Hydrate

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ACTIVE PHARMA INGREDIENTS

54 API Suppliers, 21 USDMF, 9 JDMF, 20 EU WC, 6 KDMF, 12 NDC API, 33 Listed Suppliers, $ API Reference Price

54 API Suppliers
21 USDMF
9 JDMF
20 EU WC
6 KDMF
12 NDC API
33 Listed Suppliers
$ API Reference Price

DEVELOPMENTS

1 Drugs in Development

1 Drugs in Development

INTERMEDIATES

6 Intermediates Suppliers

6 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

162 FDF Dossiers, 27 FDA Orange Book, 44 Europe, 10 Canada, 64 Australia, 17 Listed Dossiers

162 FDF Dossiers
27 FDA Orange Book
44 Europe
10 Canada
64 Australia
17 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

TABLET;ORAL - 125MG, TABLET;ORAL - 62.5MG

drugProductComposition
TABLET;ORAL - 125MG
TABLET;ORAL - 62.5MG

RELATED EXCIPIENT COMPANIES

1 Evonik, 2 Rochem International Inc, 5 SPI Pharma, 3 DKSH, 1 Jai Radhe Sales, 3 Faran Shimi Pharmaceutical, 2 Boai NKY Pharmaceuticals Ltd, 12 Gangwal Healthcare, 1 ACG Worldwide, 1 Aeon Procare, 8 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 1 BASF, 11 Corel Pharma Chem, 4 DFE Pharma, 7 Gangwal Chemicals, 5 Ideal Cures Pvt Ltd, 4 Ingredion Pharma Solutions, 15 Kerry, 4 Kima Chemical, 6 Lonza Capsugel, 8 Microlex e.U, 1 Novo Excipients, 2 Pharmatrans-Sanaq, 3 Pluviaendo, 4 Prachin Chemical, 1 Qianhao Chemical (Hebei) Co., Ltd, 1 Qualicaps, 18 Roquette, 7 Seppic, 5 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 11 Sigachi Industries, 3 The Dow Chemical Company, 1 Ulanqab Kema New Material, 4 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

44 Coating Systems & Additives, 43 Fillers, Diluents & Binders, 28 Disintegrants & Superdisintegrants, 23 Direct Compression, 23 Controlled & Modified Release, 16 Thickeners and Stabilizers, 14 Lubricants & Glidants, 13 Granulation, 12 Co-Processed Excipients, 12 Taste Masking, 11 Film Formers & Plasticizers, 7 Chewable & Orodispersible Aids, 5 Empty Capsules, 4 Vegetarian Capsules, 4 API Stability Enhancers, 4 Coloring Agents, 4 Emulsifying Agents, 3 Rheology Modifiers, 2 Solubilizers, 1 Topical

DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow, 27 NEWS #PharmaBuzz

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2 DATA COMPILATION #PharmaFlow
27 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions, 29 Finished Drug Prices, 4 Annual Reports

globalSalesInformation
2 US Medicaid Prescriptions
29 Finished Drug Prices
4 Annual Reports

MARKET PLACE

7 APIs

marketPlace
7 APIs

PATENTS & EXCLUSIVITIES

2 US Patents, 3 US Exclusivities, 2 Health Canada Patents

patents
2 US Patents
3 US Exclusivities
2 Health Canada Patents

REF. STANDARDS & IMPURITIES

6 USP , 6 Others

otherSolutions
6 USP
6 Others

ANALYTICAL

2 BioAnalytical Methods

otherMethods
2 BioAnalytical Methods

Bosentan Hydrate

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 2,826

MARKET PLACE

API

FDF

6INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

162

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

1DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

48,563,669

Annual Reports (USD Million)

2,300

Finished Drug Prices

165 RELATED EXCIPIENT COMPANIES

273EXCIPIENTS BY APPLICATIONS

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

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 Formula	C₂₇H₂₉N₅O₆S
Molecular Weight	551.6 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	11
Exact Mass	551.18385484 g/mol
Monoisotopic Mass	551.18385484 g/mol
Topological Polar Surface Area	154 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	839
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Tracleer
PubMed Health	Bosentan (By mouth)
Drug Classes	Antihypertensive
Drug Label	Tracleer 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 Ingredient	Bosentan
Dosage Form	Tablet
Route	Oral
Strength	125mg; 62.5mg
Market Status	Prescription
Company	Actelion Pharms

2 of 2
Drug Name	Tracleer
PubMed Health	Bosentan (By mouth)
Drug Classes	Antihypertensive
Drug Label	Tracleer 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 Ingredient	Bosentan
Dosage Form	Tablet
Route	Oral
Strength	125mg; 62.5mg
Market Status	Prescription
Company	Actelion 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

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 ET_A and ET_B receptors in the endothelium and vascular smooth muscle. It displays a slightly higher affinity towards ET_A receptors than ET_B 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 ET_A and ET_B.

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