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    Also known as: Rilpivirine hcl, 700361-47-3, Tmc278 hydrochloride, Edurant, Rilpivirine hydrochloride [usan], 212wax8kdd
    Molecular Formula
    C22H19ClN6
    Molecular Weight
    402.9  g/mol
    InChI Key
    KZVVGZKAVZUACK-BJILWQEISA-N
    FDA UNII
    212WAX8KDD
    Rilpivirine Hydrochloride
    A diarylpyrimidine derivative and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 that is used in the treatment of HIV INFECTIONS. It is also used in combination with other ANTI-HIV AGENTS, since ANTIVIRAL DRUG RESISTANCE emerges rapidly when it is used alone.
    1 2D Structure

    Rilpivirine Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile;hydrochloride
    2.1.2 InChI
    InChI=1S/C22H18N6.ClH/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19;/h3-9,11-13H,1-2H3,(H2,25,26,27,28);1H/b4-3+;
    2.1.3 InChI Key
    KZVVGZKAVZUACK-BJILWQEISA-N
    2.1.4 Canonical SMILES
    CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)C=CC#N.Cl
    2.1.5 Isomeric SMILES
    CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    212WAX8KDD
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 278, Tmc

    2. Hcl, Rilpivirine

    3. Hydrochloride, Rilpivirine

    4. R278474

    5. Rilpivirine

    6. Rilpivirine Hcl

    7. Tmc 278

    8. Tmc-278

    9. Tmc278

    2.3.2 Depositor-Supplied Synonyms

    1. Rilpivirine Hcl

    2. 700361-47-3

    3. Tmc278 Hydrochloride

    4. Edurant

    5. Rilpivirine Hydrochloride [usan]

    6. 212wax8kdd

    7. Rilpivirine (as Hydrochloride)

    8. 700361-47-3 (hcl)

    9. Chebi:68602

    10. (e)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile Hydrochloride

    11. Benzonitrile, 4-((4-((4-((1e)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)-, Hydrochloride (1:1)

    12. 4-[[4-[4-[(e)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile;hydrochloride

    13. Unii-212wax8kdd

    14. Endurant

    15. Edurant (tn)

    16. Rilpivirine Monohydrochloride

    17. Tmc-278 Hydrochloride

    18. Schembl1831067

    19. Tmc-278-la

    20. Tmc 278. Trade Name Edurant

    21. Chembl1628504

    22. Dtxsid80220320

    23. Bcp13350

    24. Rilpivirine Hydrochloride (jan/usan)

    25. Rilpivirine Hydrochloride [mi]

    26. Akos025149454

    27. Rilpivirine Hydrochloride [jan]

    28. 4-((4-((4-((1e)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)pyrimidin-2- Yl)amino)benzonitrile

    29. Rilpivirine Hydrochloride [vandf]

    30. Ac-30620

    31. Rilpivirine Hydrochloride [who-dd]

    32. D09958

    33. Rilpivirine Hydrochloride [orange Book]

    34. Juluca Component Rilpivirine Hydrochloride

    35. Eviplera Component Rilpivirine Hydrochloride

    36. Odefsey Component Rilpivirine Hydrochloride

    37. Rilpivirine Hydrochloride Component Of Juluca

    38. Q27137040

    39. Rilpivirine Hydrochloride Component Of Eviplera

    40. Rilpivirine Hydrochloride Component Of Odefsey

    41. 4-[[4-[[4-[(e)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile Monohydrochloride

    42. 4-{[4-({4-[(e)-2-cyanoethenyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile Hydrochloride

    43. 4-{[4-({4-[(e)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile Hydrochloride

    44. Benzonitrile, 4-((4-((4-((1e)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2- Pyrimidinyl)amino)-, Hydrochloride (1:1)

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 402.9 g/mol
    Molecular Formula C22H19ClN6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass402.1359723 g/mol
    Monoisotopic Mass402.1359723 g/mol
    Topological Polar Surface Area97.4 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity607
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameEdurant
    PubMed HealthRilpivirine (By mouth)
    Drug ClassesAntiretroviral Agent
    Active IngredientRilpivirine hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 25mg base
    Market StatusPrescription
    CompanyJanssen Prods

    2 of 2  
    Drug NameEdurant
    PubMed HealthRilpivirine (By mouth)
    Drug ClassesAntiretroviral Agent
    Active IngredientRilpivirine hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 25mg base
    Market StatusPrescription
    CompanyJanssen Prods

    4.2 Drug Indication

    Edurant, in combination with other antiretroviral medicinal products, is indicated for the treatment of human immunodeficiency virus type 1 (HIV1) infection in antiretroviral treatmentnave patients 12 years of age and older with a viral load 100,000 HIV1 RNA copies/ml.

    As with other antiretroviral medicinal products, genotypic resistance testing should guide the use of Edurant.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-HIV Agents

    Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

    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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Non-Nucleoside Analog [EXT]; Non-Nucleoside Reverse Transcriptase Inhibitors [MoA]; Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
    5.3 ATC Code

    J05AG05

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    DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;300...DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;300MG

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    DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;EQ ...DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;EQ 25MG BASE

    USFDA APPLICATION NUMBER - 208351

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