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Ambrisentan

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ACTIVE PHARMA INGREDIENTS

20 API Suppliers, 10 USDMF, 2 JDMF, 6 EU WC, 1 KDMF, 5 NDC API, 12 Listed Suppliers, $ API Reference Price

20 API Suppliers
10 USDMF
2 JDMF
6 EU WC
1 KDMF
5 NDC API
12 Listed Suppliers
$ API Reference Price

DEVELOPMENTS

3 Drugs in Development

3 Drugs in Development

INTERMEDIATES

4 Intermediates Suppliers

4 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

102 FDF Dossiers, 20 FDA Orange Book, 32 Europe, 8 Canada, 32 Australia, 4 South Africa, 6 Listed Dossiers

102 FDF Dossiers
20 FDA Orange Book
32 Europe
8 Canada
32 Australia
4 South Africa
6 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 SPI Pharma, 2 DKSH, 1 Jai Radhe Sales, 9 Gangwal Healthcare, 3 Nanjing Well Pharmaceutical, 1 Aeon Procare, 4 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 1 BASF, 5 Corel Pharma Chem, 5 DFE Pharma, 6 Gangwal Chemicals, 3 Ideal Cures Pvt Ltd, 1 Ingredion Pharma Solutions, 20 Kerry, 9 Microlex e.U, 1 Novo Excipients, 1 Pharmatrans-Sanaq, 3 Pluviaendo, 3 Prachin Chemical, 10 Roquette, 3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 11 Sigachi Industries, 3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

42 Fillers, Diluents & Binders, 20 Coating Systems & Additives, 19 Direct Compression, 15 Disintegrants & Superdisintegrants, 13 Lubricants & Glidants, 11 Co-Processed Excipients, 10 Thickeners and Stabilizers, 10 Granulation, 9 Controlled & Modified Release, 5 Film Formers & Plasticizers, 4 Parenteral, 3 Taste Masking, 2 Chewable & Orodispersible Aids, 2 Coloring Agents, 2 Topical, 2 Rheology Modifiers, 2 Emulsifying Agents, 1 API Stability Enhancers, 1 Solubilizers

DIGITAL CONTENT

1 DATA COMPILATION #PharmaFlow, 14 NEWS #PharmaBuzz

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1 DATA COMPILATION #PharmaFlow
14 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions, 26 Finished Drug Prices, 1 Annual Reports

globalSalesInformation
2 US Medicaid Prescriptions
26 Finished Drug Prices
1 Annual Reports

MARKET PLACE

6 APIs, 5 FDF Dossiers

marketPlace
6 APIs
5 FDF Dossiers

PATENTS & EXCLUSIVITIES

6 US Patents, 6 Health Canada Patents

patents
6 US Patents
6 Health Canada Patents

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 46,816

MARKET PLACE

API

FDF

4INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

102

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

3DRUGS 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)

350,219,632

Annual Reports (USD Million)

142

Finished Drug Prices

106 RELATED EXCIPIENT COMPANIES

173EXCIPIENTS BY APPLICATIONS

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 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 Formula	C₂₂H₂₂N₂O₄
Molecular Weight	378.4 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	378.15795719 g/mol
Monoisotopic Mass	378.15795719 g/mol
Topological Polar Surface Area	81.5 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	475
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

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.

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

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.

API SUPPLIERS

01

LGM Pharma

U.S.A

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Contract Pharma 2024

Booth #134

LGM Pharma accelerates & optimizes the new product pathway from early development through commercialization.

Contact Supplier

U.S.A

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

02

HRV Global Life Sciences

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Booth #3A25

HRV Global Life Sciences - Market Expansion Leader in Pharmaceuticals.

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India

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF AU

AUDIT

03

Medichem S.A

Spain

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Farmaforum 2024

Attending

Medichem is a vertically integrated pharmaceutical company specializing in the development & manufacturing of APIs & FDFs.

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Spain

Virtual Booth

Digital Content

USDMF

CEP/COS JDMF EU-WC NDC

KDMF VMF Others AUDIT

04

Megafine Pharma (P) Limited

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Attending

Megafine Pharma is engaged in the production of APIs, and advanced intermediates, and offers contract manufacturing services.

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India

Virtual Booth

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USDMF

CEP/COS JDMF EU-WC

NDC KDMF VMF CN, RU, ...

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05

Sun Pharmaceutical Industries Limi...

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX

Not Confirmed

06

Cipla

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX

Not Confirmed

07

Zhejiang Huahai Pharmaceutical

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX

Not Confirmed

08

Jiangsu Joyglory Pharmaceutical

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX

Not Confirmed

09

Viatris

U.S.A

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX

Not Confirmed

10

Tianjin Weijie Pharmaceutical Co.,...

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX

Not Confirmed

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API Reference Price

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