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Also known as: 873054-44-5, Vx-770, Kalydeco, Ivacaftor (vx-770), N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide, Vx 770

Molecular Formula

C₂₄H₂₈N₂O₃

Molecular Weight

392.5 g/mol

InChI Key

PURKAOJPTOLRMP-UHFFFAOYSA-N

FDA UNII

1Y740ILL1Z

Ivacaftor (also known as Kalydeco or VX-770) is a drug used for the management of Cystic Fibrosis (CF). It is manufactured and distributed by Vertex Pharmaceuticals. It was approved by the Food and Drug Administration on January 31, 2012, and by Health Canada in late 2012. Ivacaftor is administered as a monotherapy and also administered in combination with other drugs for the management of CF. Cystic Fibrosis is an autosomal recessive disorder caused by one of several different mutations in the gene for the Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) protein, an ion channel involved in the transport of chloride and sodium ions across cell membranes. CFTR is active in epithelial cells of organs such as of the lungs, pancreas, liver, digestive system, and reproductive tract. Alterations in the CFTR gene result in altered production, misfolding, or function of the protein and consequently abnormal fluid and ion transport across cell membranes. As a result, CF patients produce thick, sticky mucus that clogs the ducts of organs where it is produced making patients more susceptible to complications such as infections, lung damage, pancreatic insufficiency, and malnutrition. Prior to the development of ivacaftor, management of CF primarily involved therapies for the control of infections, nutritional support, clearance of mucus, and management of symptoms rather than improvements in the underlying disease process or lung function (FEV1). Notably, ivacaftor was the first medication approved for the management of the underlying causes of CF (abnormalities in CFTR protein function) rather than control of symptoms.

Ivacaftor is a Cystic Fibrosis Transmembrane Conductance Regulator Potentiator. The mechanism of action of ivacaftor is as a Chloride Channel Activation Potentiator, and Cytochrome P450 2C9 Inhibitor, and P-Glycoprotein Inhibitor, and Cytochrome P450 3A Inhibitor.

1 2D Structure

Ivacaftor

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(2,4-ditert-butyl-5-hydroxyphenyl)-4-oxo-1H-quinoline-3-carboxamide

2.1.2 InChI

InChI=1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)

2.1.3 InChI Key

PURKAOJPTOLRMP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C)C1=CC(=C(C=C1NC(=O)C2=CNC3=CC=CC=C3C2=O)O)C(C)(C)C

2.2 Other Identifiers

2.2.1 UNII

1Y740ILL1Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-quinolinecarboxamide, N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-1,4-dihydro-4-oxo-

2. Kalydeco

3. N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

4. N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

5. Vx-770

2.3.2 Depositor-Supplied Synonyms

1. 873054-44-5

2. Vx-770

3. Kalydeco

4. Ivacaftor (vx-770)

5. N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

6. Vx 770

7. N-[2,4-bis(tert-butyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxo-3-quinolinecarboxamide

8. Chebi:66901

9. N-(2,4-ditert-butyl-5-hydroxyphenyl)-4-oxo-1h-quinoline-3-carboxamide

10. 1y740ill1z

11. 1413431-05-6

12. 3-quinolinecarboxamide, N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-1,4-dihydro-4-oxo-

13. N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

14. Vx770

15. 3-quinolinecarboxamide, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxo-

16. Kalydeco (tn)

17. Ivacaftor [usan]

18. Ivacaftor [usan:inn]

19. Ivacaftorum

20. Unii-1y740ill1z

21. Ivacaftor D18

22. Vx7

23. Ivacaftor [inn]

24. Ivacaftor [mi]

25. Ivacaftor (usan/inn)

26. Vx-770 - Ivacaftor

27. Ivacaftor [vandf]

28. Ivacaftor [who-dd]

29. Mls006011119

30. Schembl351373

31. Gtpl4342

32. Ivacaftor [orange Book]

33. Vx-770, Ivacaftor, Kalydeco

34. Chembl2010601

35. Dtxsid00236281

36. Ex-a441

37. Orkambi Component Ivacaftor

38. Symkevi Component Ivacaftor

39. Bcpp000199

40. Hms3654e10

41. Hms3744k05

42. Trikafta Component Ivacaftor

43. Bcp19794

44. Bdbm50032693

45. Mfcd17171361

46. S1144

47. Zinc52509463

48. Ivacaftor Component Of Orkambi

49. Akos015994762

50. Akos032950001

51. Ivacaftor Component Of Trikafta

52. Bcp9000799

53. Ccg-268562

54. Cs-0497

55. Db08820

56. Ex-7211

57. Le-0002

58. Sb16815

59. Ncgc00242480-01

60. Ncgc00242480-03

61. Ac-28324

62. Hy-13017

63. Smr004702900

64. Ft-0696681

65. Sw219620-1

66. Ec-000.2478

67. A25626

68. D09916

69. Ab01565806_02

70. Q6095693

71. Ctp-656; Ctp-656; Ctp-656; D9-ivacaftor;vx-561

72. Cystic Fibrosis Transmembrane Conductance Regulator Potentiator

73. N-(5-hydroxy-2,4-ditert-butyl-phenyl)-4-oxo-1h-quinoline-3-carboxamide

74. N-(2,4-ditert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

75. N-(5-hydroxy-2,4-bis(2-methyl-2-propanyl)phenyl]-4-oxo-1,4-dihydro-3-quinolinecarboxamide

76. N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide

77. 1134822-00-6

78. Ivacaftor;n-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide;ivacaftor

2.4 Create Date

2007-07-23

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₈N₂O₃
Molecular Weight	392.5 g/mol
XLogP3	5.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	392.20999276 g/mol
Monoisotopic Mass	392.20999276 g/mol
Topological Polar Surface Area	78.4 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	671
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	Kalydeco
PubMed Health	Ivacaftor (By mouth)
Drug Classes	Respiratory Agent
Drug Label	The active ingredient in KALYDECO tablets is ivacaftor, which has the following chemical name: N-(2,4-di-tert-butyl-5-hydroxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxamide. Its molecular formula is C24H28N2O3 and its molecular weight is 392.49. Iva...
Active Ingredient	Ivacaftor
Dosage Form	Tablet
Route	Oral
Strength	150mg
Market Status	Prescription
Company	Vertex Pharms

2 of 2
Drug Name	Kalydeco
PubMed Health	Ivacaftor (By mouth)
Drug Classes	Respiratory Agent
Drug Label	The active ingredient in KALYDECO tablets is ivacaftor, which has the following chemical name: N-(2,4-di-tert-butyl-5-hydroxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxamide. Its molecular formula is C24H28N2O3 and its molecular weight is 392.49. Iva...
Active Ingredient	Ivacaftor
Dosage Form	Tablet
Route	Oral
Strength	150mg
Market Status	Prescription
Company	Vertex Pharms

4.2 Drug Indication

When used as monotherapy as the product Kalydeco, ivacaftor is indicated for the management of CF in patients age 2 years and older who have a mutation in the CFTR gene that is responsive to ivacaftor potentiation. Ivacaftor received expanded approval in May 2017 for the following 33 CFTR mutations: E56K, P67L, R74W, D110E, D110H, R117C, R117H, G178R, E193K, L206W, R347H, R352Q, A455E, S549N, S549R, G551D, G551S, D579G, S945L, S977F, F1052V, K1060T, A1067T, G1069R, R1070Q, R1070W, F1074L, D1152H, G1244E, S1251N, S1255P, D1270N, and G1349D. When used in combination with the drug [lumacaftor] as the product Orkambi, ivacaftor is indicated for the management of CF patients age 6 years and older who are shown to be homozygous for the F508del mutation in the CFTR gene. When used in combination with [tezacaftor] in the product Symdeko, it is used to manage CF in patients 12 years and older who have at least one mutation in the CFTR gene or patients aged 12 or older who are shown to be homozygous for the F508del mutation. When used in combination with tezacaftor and [elexacaftor] in the product Trikafta, it is indicated for the treatment of cystic fibrosis in patients 12 years of age and older who have at least one _F508del_ mutation in the CFTR gene.

FDA Label

Kalydeco tablets are indicated:

- As monotherapy for the treatment of adults, adolescents, and children aged 6 years and older and weighing 25 kg or more with cystic fibrosis (CF) who have an R117H CFTR mutation or one of the following gating (class III) mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) gene: G551D, G1244E, G1349D, G178R, G551S, S1251N, S1255P, S549N or S549R (see sections 4. 4 and 5. 1).

- In a combination regimen with tezacaftor/ivacaftor tablets for the treatment of adults, adolescents, and children aged 6 years and older with cystic fibrosis (CF) who are homozygous for the F508del mutation or who are heterozygous for the F508del mutation and have one of the following mutations in the CFTR gene: P67L, R117C, L206W, R352Q, A455E, D579G, 711+3AG, S945L, S977F, R1070W, D1152H, 2789+5GA, 3272 26AG, and 3849+10kbCT.

- In a combination regimen with ivacaftor/tezacaftor/elexacaftor tablets for the treatment of adults, adolescents, and children aged 6 years and older with cystic fibrosis (CF) who have at least one F508del mutation in the CFTR gene (see section 5. 1).

Kalydeco granules are indicated for the treatment of infants aged at least 4 months, toddlers and children weighing 5 kg to less than 25 kg with cystic fibrosis (CF) who have an R117H CFTR mutation or one of the following gating (class III) mutations in the CFTR gene: G551D, G1244E, G1349D, G178R, G551S, S1251N, S1255P, S549N or S549R (see sections 4. 4 and 5. 1).

5 Pharmacology and Biochemistry

5.1 Pharmacology

The use of Ivacaftor has been shown to both improve CF symptoms and modulate underlying disease pathology. This is achieved by potentiating the channel opening probability (or gating) of CFTR protein in patients with impaired gating mechanisms. This is in contrast to [DB09280], another CF medication, that functions by preventing misfolding of the CFTR protein and thereby results in increased processing and trafficking of mature protein to the cell surface. Results from clinical trials indicated that treatment with ivacaftor results in improved lung function, reduced chance of experiencing a pulmonary exacerbation, reduced sweat chloride, increased weight gain, and improvements in CF symptoms and quality of life. When combined with tezacaftor, significant improvements in lung function have been observed in clinical studies. Ivacaftor was not found to increase the QTc interval in a clinically significant manner. Although ivacaftor given alone has not shown any significant improvements in patients with the delta-F508 mutation, it has shown significant improvements (>10% increase in FEV1 from baseline) in lung function for the following mutations: E56K, P67L, R74W, D110E, D110H, R117C, R117H, G178R, E193K, L206W, R347H, R352Q, A455E, S549N, S549R, G551D, G551S, D579G, S945L, S977F, F1052V, K1060T, A1067T, G1069R, R1070Q, R1070W, F1074L, D1152H, G1244E, S1251N, S1255P, D1270N, and G1349. This list was expanded by the FDA in May 2017 from 10 to 33 to accommodate more rare mutations. It is important to note that this drug may cause an increase in liver transaminases (ALT, AST). Ensure to assess liver transaminases before the initiation of treatment, every 3 months during the first year of administration, followed by every year thereafter.

5.2 MeSH Pharmacological Classification

Chloride Channel Agonists

A class of drugs that stimulate chloride ion influx through cell membrane channels. (See all compounds classified as Chloride Channel Agonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

IVACAFTOR

5.3.2 FDA UNII

1Y740ILL1Z

5.3.3 Pharmacological Classes

Cystic Fibrosis Transmembrane Conductance Regulator Potentiator [EPC]; Cytochrome P450 2C9 Inhibitors [MoA]; Cytochrome P450 3A Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Chloride Channel Activation Potentiators [MoA]

5.4 ATC Code

R07AX02

R07AX30

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

R - Respiratory system

R07 - Other respiratory system products

R07A - Other respiratory system products

R07AX - Other respiratory system products

R07AX02 - Ivacaftor

5.5 Absorption, Distribution and Excretion

Absorption

Ivacaftor is well absorbed in the gastrointestinal tract. Following administration of ivacaftor with fat-containing foods, peak plasma concentrations were reached at 4 hours (Tmax) with a maximum concentration (Cmax) of 768 ng/mL and AUC of 10600 ng * hr/mL. It is recommended that ivacaftor is taken with fat-containing foods as they increase absorption by approximately 2.5- to 4-fold.

Route of Elimination

After oral administration, ivacaftor is mainly eliminated in the feces after metabolic conversion and this elimination represents 87.8% of the dose. From the total eliminated dose, the metabolites M1 and M6 account for the majority of the eliminated dose, being 22% for M1 and 43% for M6. Ivacaftor shows negligible urinary excretion as the unchanged drug.

Volume of Distribution

After oral administration of 150 mg every 12 hours for 7 days to healthy volunteers in a fed state, the mean (SD) for apparent volume of distribution was 353 (122) L.

Clearance

The CL/F (SD) for the 150 mg dose was 17.3 (8.4) L/hr in healthy subjects.

5.6 Metabolism/Metabolites

Ivacaftor is extensively metabolized in humans. In vitro and clinical studies indicate that ivacaftor is primarily metabolized by CYP3A. From this metabolism, the major formed metabolites are M1 and M6. M1 is considered pharmacologically active even though it just presents approximately one-sixth the effect of the parent compound ivacaftor. On the other hand, M6 is not considered pharmacologically active as it represents less than one-fiftieth of the effect of the parent compound.

5.7 Biological Half-Life

In a clinical study, the apparent terminal half-life was approximately 12 hours following a single dose of ivacaftor. One source mentions the half-life ranges from 12 to 14 hours.

5.8 Mechanism of Action

A wide variety of CFTR mutations correlate to the Cystic Fibrosis phenotype and are associated with differing levels of disease severity. The most common mutation, affecting approximately 70% of patients with CF worldwide, is known as F508del-CFTR or delta-F508 (F508), in which a deletion in the amino acid phenylalanine at position 508 results in impaired production of the CFTR protein, thereby causing a significant reduction in the amount of ion transporter present on cell membranes. Ivacaftor as monotherapy has failed to show a benefit for patients with delta-F508 mutations, most likely due to an insufficient amount of protein available at the cell membrane for interaction and potentiation by the drug. The next most common mutation, G551D, affecting 4-5% of CF patients worldwide is characterized as a missense mutation, whereby there is sufficient amount of protein at the cell surface, but opening and closing mechanisms of the channel are altered. Ivacaftor is indicated for the management of CF in patients with this second type of mutation, as it binds to and potentiates the channel opening ability of CFTR proteins on the cell membrane. Ivacaftor exerts its effect by acting as a potentiator of the CFTR protein, an ion channel involved in the transport of chloride and sodium ions across cell membranes of the lungs, pancreas, and other organs. Alterations in the CFTR gene result in altered production, misfolding, or function of the protein and consequently abnormal fluid and ion transport across cell membranes. Ivacaftor improves CF symptoms and underlying disease pathology by potentiating the channel open probability (or gating) of CFTR protein in patients with impaired CFTR gating mechanisms. The overall level of ivacaftor-mediated CFTR chloride transport is dependent on the amount of CFTR protein at the cell surface and how responsive a particular mutant CFTR protein is to ivacaftor potentiation.

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API Reference Price

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