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Chemistry

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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 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 Formula	C₁₉H₂₀Br₂N₆O₄S
Molecular Weight	588.3 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	11
Exact Mass	587.96130 g/mol
Monoisotopic Mass	585.96335 g/mol
Topological Polar Surface Area	137 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	642
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	Opsumit
PubMed Health	Macitentan (By mouth)
Drug Classes	Antihypertensive
Drug Label	OPSUMIT (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 Ingredient	Macitentan
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Actelion Pharms

2 of 2
Drug Name	Opsumit
PubMed Health	Macitentan (By mouth)
Drug Classes	Antihypertensive
Drug Label	OPSUMIT (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 Ingredient	Macitentan
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Actelion 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

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 (E_A and E_B) 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 E_A and E_B receptors, with endothelins -1 and -2 having more affinity than endothelin-3. Binding to the Gq coupled E_A 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. E_A receptor activation is also known to contribute to pulmonary artery smooth muscle cell proliferation. The binding of endothelins to the E_B receptors acts in opposition to E_A 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 E_B receptors on endothelial cells, they are still present on smooth muscle cells and may contribute to cell proliferation through the same mechanisms as E_A receptors. Macitentan is thought to provide its therapeutic effect primarily via blocking signaling through E_A 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 E_B is less likely to contribute to a therapeutic effect as this signaling is responsible for the counter-regulatory vasodilatory signal.

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USDMF

01

Alembic Pharmaceuticals Ltd

India

Medlab Asia & Asia Health

Not Confirmed

02

Apitoria Pharma Private Ltd

India

Medlab Asia & Asia Health

Not Confirmed

03

Honour Lab Ltd

India

Medlab Asia & Asia Health

Not Confirmed

04

Laurus Labs Ltd

India

Medlab Asia & Asia Health

Not Confirmed

05

Msn Life Sciences Private Ltd

India

Medlab Asia & Asia Health

Not Confirmed

06

Raks Pharma Pvt Ltd

India

Medlab Asia & Asia Health

Not Confirmed

07

Seasons Biotechnology (taizhou) Co L...

China

Medlab Asia & Asia Health

Not Confirmed

08

Teva Pharmaceutical Industries Ltd

Israel

CPhI WW Frankfurt

Booth #6.1A32

09

Tianish Laboratories Private Ltd

U.S.A

Medlab Asia & Asia Health

Not Confirmed

10

Zhejiang Guobang Pharmaceutical Co L...

China

Medlab Asia & Asia Health

Not Confirmed

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API Reference Price

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