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    Chemistry

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    Also known as: 177036-94-1, Letairis, Volibris, Lu-208075, Bsf 208075, Bsf-208075
    Molecular Formula
    C22H22N2O4
    Molecular Weight
    378.4  g/mol
    InChI Key
    OUJTZYPIHDYQMC-LJQANCHMSA-N
    FDA UNII
    HW6NV07QEC
    Ambrisentan
    Ambrisentan is an orally bioavailable, selective antagonist of the endothelin type-A (ETA) receptor that may be used for the treatment of pulmonary arterial hypertension (PAH). Upon administration, ambrisentan targets and binds to ETA receptor, which prevents the binding of endothelin-1 (ET-1) to the ETA receptor and ET-1/ETA-mediated vasoconstriction and cell proliferation. This may lead to vasodilation. ET-1 concentrations are increased in plasma as well as lung tissue in PAH, and ET-1 may play a key role in the pathogenesis of PAH.
    Ambrisentan is an Endothelin Receptor Antagonist. The mechanism of action of ambrisentan is as an Endothelin Receptor Antagonist.
    1 2D Structure

    Ambrisentan

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoic acid
    2.1.2 InChI
    InChI=1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1
    2.1.3 InChI Key
    OUJTZYPIHDYQMC-LJQANCHMSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=NC(=N1)OC(C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
    2.1.5 Isomeric SMILES
    CC1=CC(=NC(=N1)O[C@H](C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
    2.2 Other Identifiers
    2.2.1 UNII
    HW6NV07QEC
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (+)-(2s)-2-((4,6-dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic Acid

    2. (+)-ambrisentan

    3. (+-)-ambrisentan

    4. (-)-ambrisentan

    5. (r)-ambrisentan

    6. (s)-ambrisentan

    7. Ambrisentan, (+-)-

    8. Ambrisentan, (-)-

    9. Ambrisentan, (r)-

    10. Bsf 208075

    11. Bsf-208075

    12. Bsf208075

    13. Gsk 1325760

    14. Gsk 1325760a

    15. Gsk-1325760

    16. Gsk-1325760a

    17. Gsk1325760

    18. Gsk1325760a

    19. Letairis

    20. Lu 208075

    21. Lu-208075

    22. Lu208075

    23. Volibris

    2.3.2 Depositor-Supplied Synonyms

    1. 177036-94-1

    2. Letairis

    3. Volibris

    4. Lu-208075

    5. Bsf 208075

    6. Bsf-208075

    7. Lu 208075

    8. (s)-2-((4,6-dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic Acid

    9. (s)-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoic Acid

    10. (2s)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoic Acid

    11. Gsk1325760a

    12. Gsk-1325760a

    13. Hw6nv07qec

    14. Gsk1325760

    15. Gsk-1325760

    16. Chembl1111

    17. Dsstox_cid_26282

    18. Dsstox_rid_81508

    19. Dsstox_gsid_46282

    20. Ambrisentan [inn]

    21. Lu208075

    22. (2s)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic Acid

    23. (s)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic Acid

    24. Cas-177036-94-1

    25. Unii-hw6nv07qec

    26. Ambrisentan [inn:ban:jan]

    27. Ncgc00160662-01

    28. Letairis (tn)

    29. Volibris (tn)

    30. Ambrisentan- Bio-x

    31. Ambrisentan (jan/inn)

    32. Ambrisentan [mi]

    33. Ambrisentan [jan]

    34. Ambrisentan [vandf]

    35. Schembl3679

    36. Ambrisentan [mart.]

    37. Ambrisentan [who-dd]

    38. Ambrisentan, (+)-

    39. Mls006010218

    40. Ambrisentan [ema Epar]

    41. Gtpl3951

    42. Dtxsid4046282

    43. Ambrisentan [orange Book]

    44. Chebi:135949

    45. Zinc538627

    46. Ex-a3315

    47. Tox21_111967

    48. Bdbm50146710

    49. Fd7219

    50. Mfcd09842330

    51. S2097

    52. Akos015994540

    53. Tox21_111967_1

    54. Ac-9015

    55. Ccg-268386

    56. Cs-0447

    57. Db06403

    58. De-0223

    59. (+)-(2s)-2-((4,6-dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic Acid

    60. (+-)-(2s)-2-((4,6-dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic Acid

    61. Ncgc00160662-02

    62. Ncgc00346730-01

    63. Ba164153

    64. Benzenepropanoic Acid, Alpha-[(4,6-dimethyl-2-pyrimidinyl)oxy]-beta-methoxy-beta-phenyl-, (alphas)-

    65. Hy-13209

    66. Smr004701307

    67. Sw219060-1

    68. D07077

    69. Ab01566890_01

    70. Q410789

    71. J-519579

    72. (?s)-?-[(4,6-dimethyl-2-pyrimidinyl)oxy]-?-methoxy-?-phenylbenzenepropanoic Acid

    73. (2s)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-di(phenyl)propanoic Acid

    74. (2s)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy- 3,3-diphenylpropanoic Acid

    75. (s)-2-(4,6-dimethyl-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl-propionic Acid

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 378.4 g/mol
    Molecular Formula C22H22N2O4
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count7
    Exact Mass378.15795719 g/mol
    Monoisotopic Mass378.15795719 g/mol
    Topological Polar Surface Area81.5 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity475
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Ambrisentan is indicated for treatment of idiopathic (primary) pulmonary arterial hypertension (IPAH) and pulmonary arterial hypertension (PAH) associated with connective tissue disease in patients with WHO functional class II or III symptoms. In the United States of America, ambrisentan is also indicated in combination with tadalafil to reduce the risks of disease progression and hospitalization for worsening PAH, and to improve exercise ability.

    FDA Label

    Ambrisentan Mylan is indicated for the treatment of pulmonary arterial hypertension (PAH) in adult patients of WHO Functional Class (FC) II to III, including use in combination treatment. Efficacy has been shown in idiopathic PAH (IPAH) and in PAH associated with connective tissue disease.

    Ambrisentan Mylan is indicated for the treatment of pulmonary arterial hypertension (PAH) in adult patients of WHO Functional Class (FC) II to III, including use in combination treatment. Efficacy has been shown in idiopathic PAH (IPAH) and in PAH associated with connective tissue disease.

    Volibris is indicated for treatment of pulmonary arterial hypertension (PAH) in adult patients of WHO Functional Class (FC) II to III, including use in combination treatment (see section 5. 1). Efficacy has been shown in idiopathic PAH (IPAH) and in PAH associated with connective tissue disease.

    Volibris is indicated for treatment of PAH in adolescents and children (aged 8 to less than 18 years) of WHO Functional Class (FC) II to III including use in combination treatment. Efficacy has been shown in IPAH, familial, corrected congenital and in PAH associated with connective tissue disease (see section 5. 1).

    Pulmonary arterial hypertension

    Treatment of pulmonary arterial hypertension

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ambrisentan 10 mg daily had no significant effect on the QTc interval, whereas a 40 mg daily dose of ambrisentan increased mean QTc at tmax by 5 ms with an upper 95% confidence limit of 9 ms. Significant QTc prolongation is not expected in patients taking ambrisentan without concomitant metabolic inhibitors. Plasma concentrations of B-type natriuretic peptide (BNP) in patients who received ambrisentan for 12 weeks were significantly decreased. Two Phase III placebo-controlled studies demonstrated a decrease in BNP plasma concentrations by 29% in the 2.5 mg group, 30% in the 5 mg group, and 45% in the 10 mg group (p < 0.001 for each dose group) and an increase by 11% in the placebo group.

    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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    AMBRISENTAN
    5.3.2 FDA UNII
    HW6NV07QEC
    5.3.3 Pharmacological Classes
    Endothelin Receptor Antagonists [MoA]; Endothelin Receptor Antagonist [EPC]
    5.4 ATC Code

    C02KX02

    C02KX02

    C02KX02

    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

    C02KX02 - Ambrisentan

    5.5 Absorption, Distribution and Excretion

    Absorption

    Ambrisentan is rapidly absorbed with peak plasma concentrations occuring around 2 hours after oral administration. Cmax and AUC increase proportionally with dose across the therapeutic dosing range. Absolute oral bioavailability of ambrisentan is unknown. Absorption is not affected by food.

    Route of Elimination

    Ambrisentan is primarily cleared by non-renal pathways. Along with its metabolites, ambrisentan is primarily found in the feces following hepatic and/or extra-hepatic metabolism. Approximately 22% of the administered dose is recovered in the urine following oral administration with 3.3% being unchanged ambrisentan.

    Volume of Distribution

    Ambrisentan has a low distribution into red blow cells, with a mean blood:plasma ratio of 0.57 and 0.61 in males and females, respectively.

    Clearance

    The mean oral clearance of ambrisentan was found to be 38 mL/min in healthy subjects and 19 mL/min in patients with pulmonary artery hypertension.

    5.6 Metabolism/Metabolites

    Ambrisentan is a metabolized primarily by uridine 5-diphosphate glucuronosyltransferases (UGTs) 1A9S, 2B7S,1A3S to form ambrisentan glucuronide. Ambrisentan is also metabolized to a lesser extent by CYP3A4, CYP3A5 and CYP2C19 to form 4- hydroxymethyl ambrisentan which is further glucuronidated to 4-hydroxymethyl ambrisentan glucuronide.

    5.7 Biological Half-Life

    Ambrisentan has a terminal half-life of 15 hours. It is thought that steady state is achieved after around 4 days of repeat-dosing.

    5.8 Mechanism of Action

    Endothelin-1 (ET-1) is an endogenous peptide that acts on the endothelin type A (ETA) and endothelin type B (ETB) receptors in vascular smooth muscle and endothelium. ETA-mediated actions include vasoconstriction and cell proliferation, whereas ETB predominantly mediates vasodilation, anti-proliferation, and ET-1 clearance. In patients with pulmonary arterial hypertension, ET-1 levels are increased and correlate with increased right arterial pressure and severity of disease. Ambrisentan is one of several newly developed vasodilator drugs that selectively target the endothelin type A (ETA) receptor, inhibiting its action and preventing vasoconstriction. Selective inhibition of the ETA receptor prevents phospholipase C-mediated vasoconstriction and protein kinase C-mediated cell proliferation. Endothelin type B (ETB) receptor function is not significantly inhibited, and nitric oxide and prostacyclin production, cyclic GMP- and cyclic AMP-mediated vasodilation, and endothelin-1 (ET-1) clearance is preserved.

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    27-Feb-2021
    15-Jul-2024
    KGS
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    Quantity (KGS) & Unit rate (USD/KGS) over time

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