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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
    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 Weight 435.3 g/mol
    Molecular Formula C20H15BrN6O
    XLogP34.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass434.04907 g/mol
    Monoisotopic Mass434.04907 g/mol
    Topological Polar Surface Area121 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity609
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameIntelence
    PubMed HealthEtravirine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelINTELENCE (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 IngredientEtravirine
    Dosage FormTablet
    RouteOral
    Strength200mg; 25mg; 100mg
    Market StatusPrescription
    CompanyJanssen R And D

    2 of 2  
    Drug NameIntelence
    PubMed HealthEtravirine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelINTELENCE (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 IngredientEtravirine
    Dosage FormTablet
    RouteOral
    Strength200mg; 25mg; 100mg
    Market StatusPrescription
    CompanyJanssen 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

    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.

    API Reference Price

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    27-Jan-2021
    01-Sep-2023
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DOSAGE - TABLET;ORAL - 100MG

    USFDA APPLICATION NUMBER - 22187

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