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    Chemistry

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    Also known as: 697761-98-1, Gs-9137, Jtk-303, Vitekta, Gs 9137, Elvitegravir (gs-9137)
    Molecular Formula
    C23H23ClFNO5
    Molecular Weight
    447.9  g/mol
    InChI Key
    JUZYLCPPVHEVSV-LJQANCHMSA-N
    FDA UNII
    4GDQ854U53
    Elvitegravir
    Elvitegravir is a modified quinolone antibiotic with activity against human immunodeficiency virus 1. Elvitegravir is an inhibitor of viral integrase and retains activity against integrase mutants that are resistant to Raltegravir.
    Elvitegravir is a Human Immunodeficiency Virus Integrase Strand Transfer Inhibitor. The mechanism of action of elvitegravir is as a HIV Integrase Inhibitor, and Cytochrome P450 2C9 Inducer.
    1 2D Structure

    Elvitegravir

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-[(3-chloro-2-fluorophenyl)methyl]-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxoquinoline-3-carboxylic acid
    2.1.2 InChI
    InChI=1S/C23H23ClFNO5/c1-12(2)19(11-27)26-10-16(23(29)30)22(28)15-8-14(20(31-3)9-18(15)26)7-13-5-4-6-17(24)21(13)25/h4-6,8-10,12,19,27H,7,11H2,1-3H3,(H,29,30)/t19-/m1/s1
    2.1.3 InChI Key
    JUZYLCPPVHEVSV-LJQANCHMSA-N
    2.1.4 Canonical SMILES
    CC(C)C(CO)N1C=C(C(=O)C2=C1C=C(C(=C2)CC3=C(C(=CC=C3)Cl)F)OC)C(=O)O
    2.1.5 Isomeric SMILES
    CC(C)[C@@H](CO)N1C=C(C(=O)C2=C1C=C(C(=C2)CC3=C(C(=CC=C3)Cl)F)OC)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    4GDQ854U53
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gs 9137

    2. Gs-9137

    3. Gs9137

    4. Jtk 303

    5. Jtk-303

    6. Jtk303

    7. Vitekta

    2.3.2 Depositor-Supplied Synonyms

    1. 697761-98-1

    2. Gs-9137

    3. Jtk-303

    4. Vitekta

    5. Gs 9137

    6. Elvitegravir (gs-9137)

    7. Evg

    8. Unii-4gdq854u53

    9. (s)-6-(3-chloro-2-fluorobenzyl)-1-(1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    10. 6-(3-chloro-2-fluorobenzyl)-1-[1(s)-(hydroxymethyl)-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    11. Chebi:72289

    12. 6-[(3-chloro-2-fluorophenyl)methyl]-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxoquinoline-3-carboxylic Acid

    13. Chembl204656

    14. 4gdq854u53

    15. D06677

    16. 6-(3-chloro-2-fluorobenzyl)-1-((2s)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    17. 6-(3-chloro-2-fluorobenzyl)-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    18. Jtk 303

    19. 3-quinolinecarboxylic Acid, 6-((3-chloro-2-fluorophenyl)methyl)-1,4-dihydro-1-((1s)-1-(hydroxymethyl)-2-methylpropyl)-7-methoxy-4-oxo-

    20. 6-(3-chloro-2-fluorobenzyl)-1-[(1s)-1-(hydroxymethyl)-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    21. Jtk303

    22. Elvitegravir [usan]

    23. Gs9137

    24. Elvitegravir [usan:inn]

    25. Elvitegravirum

    26. 6-(3-chloro-2-fluorobenzyl)-1-((1s)-1-(hydroxymethyl)-2-methylpropyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    27. 6-[(3-chloro-2-fluoro-phenyl)methyl]-1-[(1s)-1-(hydroxymethyl)-2-methyl-propyl]-7-methoxy-4-oxo-quinoline-3-carboxylic Acid

    28. Elv

    29. Vitekta (tn)

    30. Elvitegravir [mi]

    31. Elvitegravir (jan/usan)

    32. Elvitegravir [inn]

    33. Elvitegravir [jan]

    34. Elvitegravir (jtk-303)

    35. Elvitegravir [vandf]

    36. Elvitegravir [mart.]

    37. Mls006011136

    38. Elvitegravir [who-dd]

    39. Schembl726252

    40. Gtpl11574

    41. Bcpp000242

    42. Dtxsid101021650

    43. Elvitegravir [orange Book]

    44. Ex-a1542

    45. Bdbm50183273

    46. Mfcd11846134

    47. S2001

    48. Vitekta Component Elvitegravir

    49. Zinc13682481

    50. Elvitegravir; Gs9137; Jtk 303

    51. Stribild Component Elvitegravir

    52. Akos025396642

    53. Bcp9000642

    54. Ccg-269208

    55. Compound 2 [pmid: 18281931]

    56. Cs-0439

    57. Db09101

    58. Elvitegravir (gs-9137, Jtk-303)

    59. Elvitegravir Component Of Genvoya

    60. Elvitegravir Component Of Vitekta

    61. Elvitegravir Component Of Stribild

    62. Ncgc00346565-01

    63. Ncgc00346565-04

    64. Ncgc00346565-08

    65. Ac-29947

    66. As-16986

    67. Hy-14740

    68. Smr004702914

    69. Elvitegravir 100 Microg/ml In Acetonitrile

    70. A4070

    71. Sw219721-1

    72. Ec-000.2332

    73. Ab01274749-01

    74. Ab01274749_02

    75. J-518006

    76. Q2740966

    77. Brd-k54472332-001-01-8

    78. 3-quinolinecarboxylic Acid, 6-[(3-chloro-2-fluorophenyl)methyl]-1,4-dihydro-1-[(1s)-1-isopropyl-2-hydroxyethyl]-7-methoxy-4-oxo-

    79. 6-(3-chloro-2-fluorobenzyl)-1-[(s)-1-hydroxymethyl-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    2.4 Create Date
    2005-10-07
    3 Chemical and Physical Properties
    Molecular Weight 447.9 g/mol
    Molecular Formula C23H23ClFNO5
    XLogP35.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count7
    Exact Mass447.1248787 g/mol
    Monoisotopic Mass447.1248787 g/mol
    Topological Polar Surface Area87.1 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity702
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Elvitegravir in combination with an HIV protease inhibitor coadministered with ritonavir and with other antiretroviral drug(s) is indicated for the treatment of HIV-1 infection in antiretroviral treatment-experienced adults.

    FDA Label

    Vitekta co-administered with a ritonavir-boosted protease inhibitor and with other antiretroviral agents, is indicated for the treatment of human-immunodeficiency-virus-1 (HIV-1) infection in adults who are infected with HIV-1 without known mutations associated with resistance to elvitegravir.

    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.)

    Anti-Retroviral Agents

    Agents used to treat RETROVIRIDAE INFECTIONS. (See all compounds classified as Anti-Retroviral Agents.)

    Integrase Inhibitors

    Compounds which inhibit or antagonize biosynthesis or actions of integrase. (See all compounds classified as Integrase Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    ELVITEGRAVIR
    5.2.2 FDA UNII
    4GDQ854U53
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Cytochrome P450 2C9 Inducers
    5.3 ATC Code

    J05AX11

    J - Antiinfectives for systemic use

    J05 - Antivirals for systemic use

    J05A - Direct acting antivirals

    J05AJ - Integrase inhibitors

    J05AJ02 - Elvitegravir

    5.4 Absorption, Distribution and Excretion

    Absorption

    Following oral administration of elvitegravir and ritonavir with food, in HIV-1 infected subjects, peak elvitegravir plasma concentrations were observed approximately 4 hours post-dose.

    Route of Elimination

    Following oral administration of [14C]elvitegravir/ritonavir, 94.8% of the dose was recovered in feces, while 6.7% was recovered in urine as metabolites.

    5.5 Metabolism/Metabolites

    Elvitegravir undergoes primarily oxidative metabolism via CYP3A, and is secondarily glucuronidated via UGT1A1/3 enzymes. Metabolites are found in the plasma at very low concentrations, displayed considerably lower anti-HIV activity, and did not contribute to the overall antiviral activity of elvitegravir.

    5.6 Biological Half-Life

    The median terminal plasma half-life following administration of elvitegravir and ritonavir was approximately 8.7 hours.

    5.7 Mechanism of Action

    Elvitegravir is an HIV-1 integrase strand transfer inhibitor (INSTI). Integrase is an HIV-1 encoded enzyme that is required for viral replication. Inhibition of integrase prevents the integration of HIV-1 DNA into host genomic DNA, blocking the formation of the HIV-1 provirus and propagation of the viral infection. Elvitegravir does not inhibit human topoisomerases I or II.

    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - 150MG

    USFDA APPLICATION NUMBER - 203093

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    DOSAGE - TABLET;ORAL - 85MG

    USFDA APPLICATION NUMBER - 203093

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    DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;300M...DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;300MG

    USFDA APPLICATION NUMBER - 203100

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    DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;EQ 1...DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;EQ 10MG BASE

    USFDA APPLICATION NUMBER - 207561

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