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    Cobicistat

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    2D Structure
    Also known as: 1004316-88-4, Cobicistat (gs-9350), Gs-9350, Tybost, Gs 9350, Cobicistat,gs-9350
    Molecular Formula
    C40H53N7O5S2
    Molecular Weight
    776.0  g/mol
    InChI Key
    ZCIGNRJZKPOIKD-CQXVEOKZSA-N
    FDA UNII
    LW2E03M5PG
    A carbamate and thiazole derivative that functions as a CYTOCHROME P450 CYP3A INHIBITOR to enhance the concentration of ANTI-HIV AGENTS, with which it is used in combination, for the treatment of HIV INFECTIONS.
    Cobicistat is a Cytochrome P450 3A Inhibitor. The mechanism of action of cobicistat is as a Cytochrome P450 3A Inhibitor, and P-Glycoprotein Inhibitor, and Cytochrome P450 2D6 Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Multidrug and Toxin Extrusion Transporter 1 Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1,3-thiazol-5-ylmethyl N-[(2R,5R)-5-[[(2S)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate
    2.1.2 InChI
    InChI=1S/C40H53N7O5S2/c1-29(2)38-43-34(27-53-38)25-46(3)39(49)45-36(16-17-47-18-20-51-21-19-47)37(48)42-32(22-30-10-6-4-7-11-30)14-15-33(23-31-12-8-5-9-13-31)44-40(50)52-26-35-24-41-28-54-35/h4-13,24,27-29,32-33,36H,14-23,25-26H2,1-3H3,(H,42,48)(H,44,50)(H,45,49)/t32-,33-,36+/m1/s1
    2.1.3 InChI Key
    ZCIGNRJZKPOIKD-CQXVEOKZSA-N
    2.1.4 Canonical SMILES
    CC(C)C1=NC(=CS1)CN(C)C(=O)NC(CCN2CCOCC2)C(=O)NC(CCC(CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)CC5=CC=CC=C5
    2.1.5 Isomeric SMILES
    CC(C)C1=NC(=CS1)CN(C)C(=O)N[C@@H](CCN2CCOCC2)C(=O)N[C@H](CC[C@H](CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)CC5=CC=CC=C5
    2.2 Other Identifiers
    2.2.1 UNII
    LW2E03M5PG
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 9350, Gs

    2. Gs 9350

    3. Gs-9350

    4. Gs9350

    5. Tybost

    2.3.2 Depositor-Supplied Synonyms

    1. 1004316-88-4

    2. Cobicistat (gs-9350)

    3. Gs-9350

    4. Tybost

    5. Gs 9350

    6. Cobicistat,gs-9350

    7. Unii-lw2e03m5pg

    8. Chebi:72291

    9. Lw2e03m5pg

    10. 1,3-thiazol-5-ylmethyl [(2r,5r)-5-{[(2s)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-4-(morpholin-4-yl)butanoyl]amino}-1,6-diphenylhexan-2-yl]carbamate

    11. 1,3-thiazol-5-ylmethyl N-[(2r,5r)-5-[[(2s)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate

    12. Thiazol-5-ylmethyl ((2r,5r)-5-((s)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-4-morpholinobutanamido)-1,6-diphenylhexan-2-yl)carbamate

    13. 1,3-thiazol-5-ylmethyl N-[(2r,5r)-5-[(2s)-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}-4-(morpholin-4-yl)butanamido]-1,6-diphenylhexan-2-yl]carbamate

    14. 2,7,10,12-tetraazatridecanoic Acid, 12-methyl-13-(2-(1-methylethyl)-4-thiazolyl)-9-(2-(4-morpholinyl)ethyl)-8,11-dioxo-3,6-bis(phenylmethyl)-, 5-thiazolylmethyl Ester, (3r,6r,9s)-

    15. Cobicistat [usan]

    16. Cobicistat [usan:inn]

    17. Cobicistatum

    18. 2,7,10,12-tetraazatridecanoic Acid, 12-methyl-13-[2-(1-methylethyl)-4-thiazolyl]-9-[2-(4-morpholinyl)ethyl]-8,11-dioxo-3,6-bis(phenylmethyl)-, 5-thiazolylmethyl Ester, (3r,6r,9s)-

    19. Thiazol-5-ylmethyl (2r,5r)-5-((s)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-4-morpholinobutanamido)-1,6-diphenylhexan-2-ylcarbamate

    20. Tybost (tn)

    21. Cobicistat [mi]

    22. Cobicistat [inn]

    23. Cobicistat [jan]

    24. Cobicistat; Gs-9350

    25. Cobicistat [vandf]

    26. Cobicistat [who-dd]

    27. Cobicistat On Silicon Dioxide

    28. Cobicistat (jan/usan/inn)

    29. Gtpl7535

    30. Schembl2736227

    31. Chembl2095208

    32. Cobicistat [orange Book]

    33. Cobicistat, (r,r,s)-

    34. Dtxsid00143269

    35. Evotaz Component Cobicistat

    36. Genvoya Component Cobicistat

    37. Symtuza Component Cobicistat

    38. Bcp06630

    39. Ex-a2578

    40. Rezolsta Component Cobicistat

    41. Stribild Component Cobicistat

    42. Bdbm50447471

    43. Mfcd18251449

    44. Prezcobix Component Cobicistat

    45. S2900

    46. Zinc85537014

    47. Cobicistat Component Of Evotaz

    48. Akos025404908

    49. Cobicistat Component Of Genvoya

    50. Cobicistat Component Of Symtuza

    51. Ccg-270459

    52. Cobicistat Component Of Stribild

    53. Cs-0742

    54. Db09065

    55. Cobicistat Component Of Prezcobix

    56. Ncgc00386235-04

    57. Ncgc00386235-06

    58. Ac-28961

    59. As-17061

    60. Hy-10493

    61. Sw219553-1

    62. D09881

    63. Ab01566899_01

    64. Q5138908

    65. (1,3-thiazol-5-yl)methyl (5s,8r,11r)-8,11-dibenzyl-2-methyl-5-(2-(morpholin-4-yl)ethyl)-1-(2-(propan-2-yl)-1,3-thiazol-4-yl)-3,6-dioxo-2,4,7,12-tetraazatridecan-13-oate

    66. 1,3-thiazol-5-ylmethyl ((2r,5r)-5-(((2s)-2-((methyl((2-(propan-2-yl)-1,3-thiazol-4-yl)methyl)carbamoyl)amino)-4-(morpholin-4-yl)butanoyl)amino)-1,6-diphenylhexan-2-yl)carbamate

    67. Thiazol-5-ylmethyl ((1r,4r)-1-benzyl-4-({(2s)-2-((methyl{(2-(1-methylethyl)thiazol-4-yl)methyl}carbamoyl)amino)-4-(morpholin-4-yl)butanoyl}amino)-5-phenylpentyl)carbamate

    68. Thiazol-5-ylmethyl N-[(1r,4r)-1-benzyl-4-[[(2s)-2-[[(2-isopropylthiazol-4-yl)methyl-methyl-carbamoyl]amino]-4-morpholino-butanoyl]amino]-5-phenyl-pentyl]carbamate

    2.4 Create Date
    2009-02-23
    3 Chemical and Physical Properties
    Molecular Weight 776.0 g/mol
    Molecular Formula C40H53N7O5S2
    XLogP35.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count20
    Exact Mass775.35496016 g/mol
    Monoisotopic Mass775.35496016 g/mol
    Topological Polar Surface Area195 Ų
    Heavy Atom Count54
    Formal Charge0
    Complexity1120
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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

    Cobicistat is a CYP3A inhibitor indicated to increase systemic exposure of atazanavir or darunavir (once daily dosing regimen) in combination with other antiretroviral agents in the treatment of HIV-1 infection. It is not interchangeable with ritonavir to increase systemic exposure of darunavir 600 mg twice daily, fosamprenavir, saquinavir, or tipranavir due to lack of exposure data. The use of cobicistat is not recommended with darunavir 600 mg twice daily, fosamprenavir, saquinavir or tipranavir. Complex or unknown mechanisms of drug interactions preclude extrapolation of ritonavir drug interactions to certain cobicistat interactions. Cobicistat and ritonavir when administered with either atazanavir or darunavir may result in different drug interactions when used with concomitant medications.

    FDA Label

    Tybost is indicated as a pharmacokinetic enhancer of atazanavir 300 mg once daily or darunavir 800 mg once daily as part of antiretroviral combination therapy in human immunodeficiency virus-1 (HIV-1) infected adults and adolescents aged 12 years and older:

    - weighing at least 35 kg coadministered with atazanavir or

    - weighing at least 40 kg coadministered with darunavir.

    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.)

    Cytochrome P-450 CYP3A Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    COBICISTAT
    5.2.2 FDA UNII
    LW2E03M5PG
    5.2.3 Pharmacological Classes
    Cytochrome P450 2D6 Inhibitors [MoA]; Cytochrome P450 3A Inhibitor [EPC]; Cytochrome P450 3A Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Breast Cancer Resistance Protein Inhibitors [MoA]
    5.3 ATC Code

    V03AX03

    J05AR14

    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

    V - Various

    V03 - All other therapeutic products

    V03A - All other therapeutic products

    V03AX - Other therapeutic products

    V03AX03 - Cobicistat

    5.4 Absorption, Distribution and Excretion

    Absorption

    Median peak plasma concentrations were observed at 3.5 hours post-dose.

    Route of Elimination

    With single dose administration of [14C] cobicistat after multiple dosing of cobicistat for six days, the mean percent of the administered dose excreted in feces and urine was 86.2% and 8.2%, respectively.

    5.5 Metabolism/Metabolites

    Cobicistat is metabolized by CYP3A and to a minor extent by CYP2D6 enzymes and does not undergo glucuronidation.

    5.6 Biological Half-Life

    The terminal plasma half-life of cobicistat is approximately 3 to 4 hours.

    5.7 Mechanism of Action

    Cobicistat is a mechanism-based inhibitor of cytochrome P450 3A (CYP3A) isoforms. Inhibition of CYP3A-mediated metabolism by cobicistat increases the systemic exposure of CYP3A substrates atazanavir and darunavir and therefore enables increased anti-viral activity at a lower dosage. Cobicistat does not have any anti-HIV activity on its own.