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Etravirine

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Synopsis

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Chemistry

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Also known as: 269055-15-4, Intelence, Tmc-125, Tmc125, Etravirine (tmc125), Tmc 125

Molecular Formula

C₂₀H₁₅BrN₆O

Molecular Weight

435.3 g/mol

InChI Key

PYGWGZALEOIKDF-UHFFFAOYSA-N

FDA UNII

0C50HW4FO1

Etravirine is a diarylpyrimidine non-nucleoside reverse transcriptase inhibitor. Etravirine is designed to be active against HIV isolates with mutations that confer resistance to the two most commonly prescribed first-generation NNRTIs. It can bind the enzyme reverse transcriptase (RT) in multiple conformations, both for native and mutant RT, thereby blocking the enzymatic activity of RT.

Etravirine is a Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of etravirine is as a Non-Nucleoside Reverse Transcriptase Inhibitor, and Cytochrome P450 3A Inducer, and Cytochrome P450 2C9 Inhibitor, and Cytochrome P450 2C19 Inhibitor, and P-Glycoprotein Inhibitor.

1 2D Structure

Etravirine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile

2.1.2 InChI

InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)

2.1.3 InChI Key

PYGWGZALEOIKDF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=CC(=C1OC2=NC(=NC(=C2Br)N)NC3=CC=C(C=C3)C#N)C)C#N

2.2 Other Identifiers

2.2.1 UNII

0C50HW4FO1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-benzonitrile

2. Benzonitrile, 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-

3. Intelence

4. R165335

5. Tmc 125

6. Tmc-125

7. Tmc125 Cpd

2.3.2 Depositor-Supplied Synonyms

1. 269055-15-4

2. Intelence

3. Tmc-125

4. Tmc125

5. Etravirine (tmc125)

6. Tmc 125

7. R165335

8. R-165335

9. 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

10. 4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile

11. 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile

12. 0c50hw4fo1

13. Chembl308954

14. Chebi:63589

15. Etravirine-d8

16. 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-benzonitrile

17. 4-(6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

18. Benzonitrile, 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-

19. Benzonitrile, 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-

20. Benzonitrile,4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-

21. 65b

22. Intelence(tm)

23. Dapy Deriv

24. 4-(6-amino-5-bromo-2-(4-cyanophenylamino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

25. Intelence (tn)

26. Diaminopyrimidine Deriv

27. Tmc125 Cpd

28. Unii-0c50hw4fo1

29. Etravirine (jan/usan/inn)

30. Etravirine [usan:inn:ban:jan]

31. Etravirine [inn]

32. Etravirine- Bio-x

33. R 165335

34. Etravine; Etravirine

35. 4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile

36. R165335-tmc125

37. 3m8p

38. Etravirine [mi]

39. Tmc-125/r-165335

40. Etravirine [jan]

41. Etravirine [usan]

42. Etravirine [vandf]

43. Etravirine [mart.]

44. Etravirine [who-dd]

45. Schembl52691

46. Etravirine [ema Epar]

47. Etravirine [orange Book]

48. Dtxsid30181412

49. Hms3651p20

50. Zinc602632

51. Bcp03562

52. Ex-a4282

53. Bdbm50103642

54. S3080

55. 4-({6-amino-5-bromo-2-[(4-

56. Akos015896355

57. Ac-8503

58. Bcp9000006

59. Ccg-269074

60. Cs-0435

61. Db06414

62. He-0088

63. Pb32778

64. 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile

65. 4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrile

66. Ncgc00345885-02

67. Ncgc00345885-04

68. Ba164437

69. Hy-90005

70. Bcp0726000193

71. Db-067700

72. Am20080899

73. Cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-

74. Ft-0658058

75. Ft-0668442

76. Ft-0668443

77. Sw219570-1

78. A26965

79. D04112

80. Ab01566873_01

81. A818671

82. Q414762

83. Sr-01000944895

84. J-513179

85. Sr-01000944895-1

86. 4-(6-amino-5-bromo-2-(4-cyanophenylamino)pyrimidin-4-ylamino)-3,5-dimethylbenzonitrile

87. 4-[[4-amino 5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile

88. 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]-amino]benzonitrile

89. 4-[[6-amino-5-bromo-2-(4-cyanoanilino)-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile

90. 4-[6-amino-5-bromo-2-(4-cyano-phenylamino)-pyrimidin-4-yloxy]-3,5-dimethyl-benzonitrile

91. 4-((6-amino-5-bromo-2-((4-cyanophenyl) Amino) Pyrimidin-4-yl) Oxy)-3, 5-dimethylbenzonitrile

92. 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 Cdimethylbenzonitrile

93. 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl -benzonitrile

94. 4-[6-azanyl-5-bromanyl-2-[(4-cyanophenyl)amino]pyrimidin-4-yl]oxy-3,5-dimethyl-benzenecarbonitrile

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₅BrN₆O
Molecular Weight	435.3 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	434.04907 g/mol
Monoisotopic Mass	434.04907 g/mol
Topological Polar Surface Area	121 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	609
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	Intelence
PubMed Health	Etravirine (By mouth)
Drug Classes	Antiretroviral Agent
Drug Label	INTELENCE (etravirine) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) of human immunodeficiency virus type 1 (HIV-1).The chemical name for etravirine is 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzon...
Active Ingredient	Etravirine
Dosage Form	Tablet
Route	Oral
Strength	200mg; 25mg; 100mg
Market Status	Prescription
Company	Janssen R And D

2 of 2
Drug Name	Intelence
PubMed Health	Etravirine (By mouth)
Drug Classes	Antiretroviral Agent
Drug Label	INTELENCE (etravirine) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) of human immunodeficiency virus type 1 (HIV-1).The chemical name for etravirine is 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzon...
Active Ingredient	Etravirine
Dosage Form	Tablet
Route	Oral
Strength	200mg; 25mg; 100mg
Market Status	Prescription
Company	Janssen R And D

4.2 Drug Indication

Indicated as an adjunct therapy in the treatment of adult HIV-1 infections resistant to therapy with other NNRTIs and antiretroviral agents.

FDA Label

Intelence, in combination with a boosted protease inhibitor and other antiretroviral medicinal products, is indicated for the treatment of human-immunodeficiency-virus-type-1 (HIV-1) infection in antiretroviral-treatment-experienced adult patients and in antiretroviral-treatment-experienced paediatric patients from six years of age.

This indication is based on week-48 analyses from two phase-III trials in highly pretreated patients where Intelence was investigated in combination with an optimised background regimen (OBR) which included darunavir/ritonavir. The indication in paediatric patients is based on 48-week analyses of a single-arm, phase-II trial in antiretroviral-treatment-experienced paediatric patients.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Clinical trials have shown no prolongation of QT intervals on electrocardiograms after 8 days of dosing.

5.2 MeSH Pharmacological Classification

Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ETRAVIRINE

5.3.2 FDA UNII

0C50HW4FO1

5.3.3 Pharmacological Classes

Cytochrome P450 2C9 Inhibitors [MoA]; Cytochrome P450 3A Inducers [MoA]; Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]; Non-Nucleoside Analog [EXT]; Non-Nucleoside Reverse Transcriptase Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Cytochrome P450 2C19 Inhibitors [MoA]; Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]

5.4 ATC Code

J05AG04

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

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AG - Non-nucleoside reverse transcriptase inhibitors

J05AG04 - Etravirine

5.5 Absorption, Distribution and Excretion

Absorption

Maximum oral absorption is achieved in 2.5-4 hours. Absorption is unaffected by the concomitant use of oral ranitidine or omeprazole, which decrease gastric acidity. Administration under fasting conditions resulted in a near 50% decrease in systemic exposure (AUC) when compared to administration after a meal.

Route of Elimination

After a 800mg dose of radio-labelled etraverine, 93.7% was found to undergo fecal elimination, with 81.2% - 86.4% eliminated unchanged. 1.2% of the dose was renally eliminated, changed. Etravirine is dialyzable (hemodialysis).

Volume of Distribution

Distribution of etravirine into compartments other than plasma has not been evaluated in humans.

Clearance

Renal clearance of etravirine is negligible (<1.2%), thus no dose adjustments are required in patients with renal impairment. Clearance is shown to be reduced in patients with Hepatitis B and/or co-infection, however, the safety profile of etravirine does not call for dosage adjustments.

5.6 Metabolism/Metabolites

Metabolized (in vitro) by the liver CYP450 enzymes: CYP3A4, CYP2C9, CYP2C19. The major metabolites formed by a methyl hydroxylation of the dimethylbenzonitrile moiety retained less than 90% of etravirine's activity.

5.7 Biological Half-Life

Half life of 9.05-41 hours.

5.8 Mechanism of Action

Etravirine exerts its effects via direct inhibition of the reverse transcriptase enzyme of human immunodeficiency virus type 1 (HIV-1). It directly binds reverse transcriptase and consequently blocks DNA-dependent and RNA-dependent polymerase activity. Etravirine does not inhibit human DNA polymerase alpha, beta or gamma.

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API Reference Price

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