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Sitaxentan

Sitaxentan

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Also known as: Sitaxsentan, 184036-34-8, Tbc-11251, N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide, Tbc11251, Ipi-1040

Molecular Formula

C₁₈H₁₅ClN₂O₆S₂

Molecular Weight

454.9 g/mol

InChI Key

PHWXUGHIIBDVKD-UHFFFAOYSA-N

FDA UNII

J9QH779MEM

Sitaxentan was marketed under the trade name Thelin for the treatment of pulmonary arterial hypertension (PAH) by Encysive Pharmaceuticals until Pfizer purchased Encysive in February 2008. In 2010, Pfizer voluntarily removed sitaxentan from the market over concerns of hepatotoxicity.

1 2D Structure

Sitaxentan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide

2.1.2 InChI

InChI=1S/C18H15ClN2O6S2/c1-9-5-13-14(26-8-25-13)7-11(9)6-12(22)17-15(3-4-28-17)29(23,24)21-18-16(19)10(2)20-27-18/h3-5,7,21H,6,8H2,1-2H3

2.1.3 InChI Key

PHWXUGHIIBDVKD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC2=C(C=C1CC(=O)C3=C(C=CS3)S(=O)(=O)NC4=C(C(=NO4)C)Cl)OCO2

2.2 Other Identifiers

2.2.1 UNII

J9QH779MEM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. N-(4-chloro-3-methyl-5-isoxazolyl)-2-((4,5-(methylenedioxy)-o-toly)acetyl)-3-thiophenesulfonamide

2. N-(4-chloro-3-methyl-5-isoxazolyl)-2-(3,4-(methylenedioxy)-6-methyl)phenylacetyl-3-thiophenesulfonamide

3. Sitaxsentan

4. Tbc 11251

5. Tbc-11251

6. Tbc11251

2.3.2 Depositor-Supplied Synonyms

1. Sitaxsentan

2. 184036-34-8

3. Tbc-11251

4. N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide

5. Tbc11251

6. Ipi-1040

7. J9qh779mem

8. Chembl282724

9. N-(4-chloro-3-methyl-5-isoxazolyl)-2-((4,5-(methylenedioxy)-o-toly)acetyl)-3-thiophenesulfonamide

10. N-(4-chloro-3-methyl-5-isoxazolyl)-2-(3,4-(methylenedioxy)-6-methyl)phenylacetyl-3-thiophenesulfonamide

11. Tbc 11251

12. Sitaxentan [inn]

13. Ipi 1040

14. Sitaxentan [usan:inn]

15. Unii-j9qh779mem

16. Sitaxsentan [mi]

17. Sitaxentan (usan/inn)

18. Sitaxentan [usan]

19. Dsstox_cid_31462

20. Dsstox_rid_97348

21. Sitaxentan [who-dd]

22. Dsstox_gsid_57673

23. 3-thiophenesulfonamide, N-(4-chloro-3-methyl-5-isoxazolyl)-2-((6-methyl-1,3-benzodioxol-5-yl)acetyl)-

24. N-(4-chloro-3-methyl-5-isoxazolyl)-2-((2-methyl-4,5-methylenedioxyphenyl)acetyl)thiophene-3-sulfonamide

25. N-(4-chloro-3-methyl-5-isoxazolyl)-2-((3,4-(methylenedioxy)-6-methylphenyl)acetyl)-3-thiophenesulfonamide

26. Schembl803344

27. Gtpl3950

28. Dtxsid0057673

29. Chebi:135736

30. Bcp13848

31. Zinc1481831

32. Tox21_113725

33. Bdbm50058126

34. Zinc328577260

35. Cs-0402

36. Db06268

37. Sb19551

38. Ncgc00253587-01

39. Hy-76520

40. N-(4-chloro-3-methylisoxazol-5-yl)-2-(2-(6-methylbenzo-[d][1,3]dioxol-5-yl)acetyl)thiophene-3-sulfonamide

41. Db-065456

42. Tbc11251 / Tbc-11251

43. Cas-184036-34-8

44. Ft-0701871

45. D07171

46. A927076

47. Q905664

48. Sr-01000945028

49. Sr-01000945028-1

50. 2-[2-(6-methyl-benzo[1,3]dioxol-5-yl)-acetyl]-thiophene-3-sulfonic Acid (4-chloro-3-methyl-isoxazol-5-yl) Amide

51. 2-[2-(6-methyl-benzo[1,3]dioxol-5-yl)-acetyl]-thiophene-3-sulfonic Acid (4-chloro-3-methyl-isoxazol-5-yl)-amide

52. 2-[2-(6-methyl-benzo[1,3]dioxol-5-yl)-acetyl]-thiophene-3-sulfonic Acid (4-chloro-3-methyl-isoxazol-5-yl)-amide (sitaxsentan)

53. N- (4- Chloro- 3- Methyl- Oxazol- 5- Yl)- 2- [2- (6- Methylbenzo[1,3]dioxol- 5- Yl)acetyl]- Thiophene- 3- Sulfonamide

54. N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide.

55. N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-2h-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide

56. N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(6-methyl-1,3-benzodioxol-5-yl) Acetyl]-3-thiophenesulphonamide

57. N-(4-chloro-3-methyloxazol-5-yl)-2-[2-(6-methylbenzo[1,3]dioxol-5-yl)acetyl]thiophene-3-sulfonamide

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₅ClN₂O₆S₂
Molecular Weight	454.9 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	454.0060062 g/mol
Monoisotopic Mass	454.0060062 g/mol
Topological Polar Surface Area	144 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	720
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 Indication

Investigated for use/treatment in pulmonary hypertension, connective tissue diseases, hypertension, and congestive heart failure.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sitaxentan 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. Sitaxentan blocks the binding of endothelin to its receptors, thereby negating endothelin's deleterious effects.

5.2 MeSH Pharmacological Classification

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 ATC Code

C - Cardiovascular system

C02 - Antihypertensives

C02K - Other antihypertensives

C02KX - Antihypertensives for pulmonary arterial hypertension

C02KX03 - Sitaxentan

5.4 Absorption, Distribution and Excretion

Absorption

70-100%

Route of Elimination

Renal (50 to 60%) Fecal (40 to 50%)

5.5 Metabolism/Metabolites

Hepatic (CYP2C9- and CYP3A4-mediated)

5.6 Biological Half-Life

10 hours

5.7 Mechanism of Action

Sitaxentan is a competitive antagonist of endothelin-1 at the endothelin-A (ET-A) and endothelin-B (ET-B) receptors. Under normal conditions, endothelin-1 binding of ET-A or ET-B receptors causes pulmonary vasoconstriction. By blocking this interaction, Sitaxentan decreases pulmonary vascular resistance. Sitaxentan has a higher affinity for ET-A than ET-B.