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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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D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1703529000,"product":"(N.C.V IMPURTIY OF BOSENTAN (JNJ-75096333-AAA BENZENSULFONAMIDE,N-[6-CHLORO-5-(2-METHOXYPHENOXY)[2,2-BIPYRIMIDIN]-4YL)-4","address":"30 FORJETT STREET","city":"MUMBAI, MAHARASHTRA.","supplier":"JOHNSON & JOHNSON","supplierCountry":"INDIA","foreign_port":"BRUSSELS","customer":"JOHNSON & JOHNSON","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.2","unit":"GMS","unitRateFc":"1327","totalValueFC":"294.4","currency":"EUR","unitRateINR":"122548.5","date":"26-Dec-2023","totalValueINR":"24509.69","totalValueInUsd":"294.4","indian_port":"Bombay Air","hs_no":"29359090","bill_no":"9407835","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"BRUSSELS","supplierAddress":"TURNHOUTSEWEG 30 B-2340 Beerse, , BelgiumSDNF Belgium","customerAddress":"30 FORJETT STREET"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1703529000,"product":"(N.C.V IMPURTIY OF BOSENTAN (JNJ-75096450-AAA BENZENSULFONAMIDE,N-[1,6-DIHYDRO-5-(2-METHOXYPHENOXY)[2,2-BIPYRIMIDIN]-4YL","address":"30 FORJETT STREET","city":"MUMBAI, MAHARASHTRA.","supplier":"JOHNSON & JOHNSON","supplierCountry":"INDIA","foreign_port":"BRUSSELS","customer":"JOHNSON & JOHNSON","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.2","unit":"GMS","unitRateFc":"1327","totalValueFC":"294.4","currency":"EUR","unitRateINR":"122548.5","date":"26-Dec-2023","totalValueINR":"24509.69","totalValueInUsd":"294.4","indian_port":"Bombay Air","hs_no":"29359090","bill_no":"9407835","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"BRUSSELS","supplierAddress":"TURNHOUTSEWEG 30 B-2340 Beerse, , BelgiumSDNF Belgium","customerAddress":"30 FORJETT STREET"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1703529000,"product":"(N.C.V) IMPURITY OF BOSENTAN (JNJ-75096372-AAA) BENZENESULFONAMIDE,N-[6-[2-(1,1-DIMETHYLTHOXY]-5-(2-METHOXYPHENOXYYL)[2,","address":"30 FORJETT STREET","city":"MUMBAI, MAHARASHTRA.","supplier":"JOHNSON & JOHNSON","supplierCountry":"INDIA","foreign_port":"BRUSSELS","customer":"JOHNSON & JOHNSON","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.2","unit":"GMS","unitRateFc":"1327","totalValueFC":"294.4","currency":"EUR","unitRateINR":"122548.5","date":"26-Dec-2023","totalValueINR":"24509.69","totalValueInUsd":"294.4","indian_port":"Bombay Air","hs_no":"29359090","bill_no":"9407835","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"BRUSSELS","supplierAddress":"TURNHOUTSEWEG 30 B-2340 Beerse, , BelgiumSDNF Belgium","customerAddress":"30 FORJETT STREET"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1703529000,"product":"(N.C.V) IMPURITY OF BOSENTAN (JNJ-75096424-AAA)4-TERT BUTYL-N-[5-(2-METHOXYPHENOXY)-2-PYRIMIDIN-2-YL-6-(2-SEC-BUTOXYETHO","address":"30 FORJETT STREET","city":"MUMBAI, MAHARASHTRA.","supplier":"JOHNSON & JOHNSON","supplierCountry":"INDIA","foreign_port":"BRUSSELS","customer":"JOHNSON & JOHNSON","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.2","unit":"GMS","unitRateFc":"1327","totalValueFC":"294.4","currency":"EUR","unitRateINR":"122548.5","date":"26-Dec-2023","totalValueINR":"24509.69","totalValueInUsd":"294.4","indian_port":"Bombay Air","hs_no":"29359090","bill_no":"9407835","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"BRUSSELS","supplierAddress":"TURNHOUTSEWEG 30 B-2340 Beerse, , BelgiumSDNF Belgium","customerAddress":"30 FORJETT STREET"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1710441000,"product":"RE-IMPORT OF BOSENTAN 2304006390\/62923083 (INV. NO. 6770036112 - QTY. 10.48 AS PER INV.)","address":"ALEMBIC ROAD","city":"GUJARAT","supplier":"PLIVA HRVATSKA","supplierCountry":"INDIA","foreign_port":"ZAGREB","customer":"ALEMBIC PHARMACEUTICALS LIMITED","customerCountry":"INDIA","quantity":"10.54","actualQuantity":"10.542","unit":"KGS","unitRateFc":"2800","totalValueFC":"30518.6","currency":"USD","unitRateINR":"240384.7","date":"15-Mar-2024","totalValueINR":"2534135.61","totalValueInUsd":"30518.6","indian_port":"Ahmedabad Air","hs_no":"29349990","bill_no":"2591960","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"ZAGREB","supplierAddress":"PRILAZ BARUNA FILIPOVICA 25ZAGREB 10000SDNF CROATIA","customerAddress":"ALEMBIC ROAD"}]
07-Jan-2021
22-Oct-2024
KGS
overview
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Average Price (USD/KGS)

2.5k

Number of Transactions

51 - 200

Total Quantity (KGS)

2.1k

Total Value (USD)

5.3M

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

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions
FRANCE281.801,081.011 - 50
CANADA394.102,977.511 - 50
ARGENTINA108.005,693.8<10
PAKISTAN209.821,405.1<10
VIETNAM, DEMOCRATIC REP. OF110.002,264.1<10
RUSSIA65.004,351.9<10
INDIA10.543,106.1<10
CROATIA99.082,795.6<10
ALGERIA69.792,008.1<10

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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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