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    Cabotegravir

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 1051375-10-0, Gsk1265744, Gsk744, Gsk-1265744, Gsk1265744a, S-265744
    Molecular Formula
    C19H17F2N3O5
    Molecular Weight
    405.4  g/mol
    InChI Key
    WCWSTNLSLKSJPK-LKFCYVNXSA-N
    FDA UNII
    HMH0132Z1Q
    Cabotegravir, or GSK1265744, is an HIV-1 integrase inhibitor that is prescribed with the non-nucleoside reverse transcriptase inhibitor, [rilpivirine]. Early research into cabotegravir showed it had lower oral bioavailability than [dolutegravir]. The devlopment of cabotegravir was later developed to create a long acting monthly intramuscular injection. Cabotegravir was granted FDA approval on 21 January 2021.
    Cabotegravir is a Human Immunodeficiency Virus Integrase Strand Transfer Inhibitor. The mechanism of action of cabotegravir is as a HIV Integrase Inhibitor, and Organic Anion Transporter 1 Inhibitor, and Organic Anion Transporter 3 Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3R,6S)-N-[(2,4-difluorophenyl)methyl]-10-hydroxy-6-methyl-8,11-dioxo-4-oxa-1,7-diazatricyclo[7.4.0.03,7]trideca-9,12-diene-12-carboxamide
    2.1.2 InChI
    InChI=1S/C19H17F2N3O5/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27)/t9-,14+/m0/s1
    2.1.3 InChI Key
    WCWSTNLSLKSJPK-LKFCYVNXSA-N
    2.1.4 Canonical SMILES
    CC1COC2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)O
    2.1.5 Isomeric SMILES
    C[C@H]1CO[C@H]2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)O
    2.2 Other Identifiers
    2.2.1 UNII
    HMH0132Z1Q
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (3s,11ar)-n-((2,6-difluoropyridin-3-yl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro(1,3)oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide

    2. Apretude

    3. Cabotegravir Extended-release Injectable Suspension

    4. Cabotegravir Sodium

    5. Gsk-1265744

    6. Gsk-1265744a

    7. Gsk-1265744b

    8. Gsk1265744

    9. Gsk1265744a

    10. Gsk1265744b

    11. Gsk744

    12. N-((2,4-difluorophenyl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro(1,3)oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide

    13. S-265744

    14. S-265744b

    15. Sodium (3s,11ar)-8-(((2,4-difluorophenyl)methyl)carbamoyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo(3,2-a)pyrido(1,2-d)pyrazin-6-olate

    16. Vocabria

    2.3.2 Depositor-Supplied Synonyms

    1. 1051375-10-0

    2. Gsk1265744

    3. Gsk744

    4. Gsk-1265744

    5. Gsk1265744a

    6. S-265744

    7. Gsk744 Lap

    8. Gsk-1265744a

    9. Gsk744 La

    10. Gsk 744

    11. S/gsk1265744

    12. Gsk 1265744

    13. Cabotegravir (gsk744, Gsk1265744)

    14. Gsk744 (s/gsk1265744)

    15. Hmh0132z1q

    16. (3s,11ar)-n-(2,4-difluorobenzyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide

    17. Cab

    18. (3s,11ar)-n-((2,4-difluorophenyl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide

    19. Unii-hmh0132z1q

    20. Cabotegravir [usan:inn]

    21. Cabotegravirum

    22. 744 La

    23. Cabotegravir [inn]

    24. Cabotegravir [jan]

    25. Cabotegravir [usan]

    26. Schembl82803

    27. Cabotegravir [who-dd]

    28. Cabotegravir (jan/usan/inn)

    29. Cabotegravir; Gsk1265744

    30. Chembl2403238

    31. Gtpl11386

    32. Dtxsid50146982

    33. Chebi:172944

    34. Cabotegravir [orange Book]

    35. Amy27899

    36. Bcp08631

    37. Ex-a2330

    38. Bdbm50492496

    39. Mfcd25976748

    40. S7766

    41. Zinc96927633

    42. Cabenuva Component Cabotegravir

    43. S/gsk-1265744

    44. Cabenuva (cabotegravir + Rilpivirine)

    45. Ccg-268708

    46. Cs-5078

    47. Db11751

    48. Cabotegravir Component Of Cabenuva

    49. Ncgc00386434-02

    50. Ac-30895

    51. As-61279

    52. Hy-15592

    53. S/gsk1265744; Gsk744

    54. D10548

    55. P14046

    56. A902375

    57. Q15411012

    58. (3r,6s)-n-[(2,4-difluorophenyl)methyl]-10-hydroxy-6-methyl-8,11-dioxo-4-oxa-1,7-diazatricyclo[7.4.0.0?,?]trideca-9,12-diene-12-carboxamide

    59. (3r,6s)-n-[(2,4-difluorophenyl)methyl]-10-hydroxy-6-methyl-8,11-dioxo-4-oxa-1,7-diazatricyclo[7.4.0.03,7]trideca-9,12-diene-12-carboxamide

    60. (3s,11ar)-n-((2,6-difluoropyridin-3-yl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro(1,3)oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide

    61. (3s,11ar)-n-(2,4-difluorobenzyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide

    62. (3s,11ar)-n-[(2,4-difluorophenyl)methyl]-2,3,5,7,11,11a-hexahydro-6-hydroxy-3-methyl-5,7-dioxo-oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide

    63. (3s,11ar)-n-[(2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,11,11a-tetrahydrooxazolo[[?]]pyrido[[?]]pyrazine-8-carboxamide

    64. (3s,11ar)-n-[(2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide

    65. 1264720-72-0

    66. N-((2,4-difluorophenyl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro(1,3)oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide

    67. Oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide, N-((2,4-difluorophenyl)methyl)-2,3,5,7,11,11a-hexahydro-6-hydroxy-3-methyl-5,7-dioxo-, (3s,11ar)-

    2.4 Create Date
    2011-12-26
    3 Chemical and Physical Properties
    Molecular Weight 405.4 g/mol
    Molecular Formula C19H17F2N3O5
    XLogP32.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count3
    Exact Mass405.11362698 g/mol
    Monoisotopic Mass405.11362698 g/mol
    Topological Polar Surface Area99.2 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity814
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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

    Oral cabotegravir is indicated in combination with rilpivirine for the short term treatment of HIV-1 in virologically suppressed adults with no history of treatment failure to assess tolerability of cabotegravir or who have missed an injected dose of cabotegravir. Intramuscular extended-release cabotegravir is indicated in combination with rilpivirine as a complete regimen for virologically suppressed adults with no history of treatment failure. The intramuscular form is meant to replace their current antiretroviral treatment.

    Treatment of human immunodeficiency virus (HIV-1) infection

    Vocabria tablets are indicated in combination with rilpivirine tablets for the short-term treatment of Human Immunodeficiency Virus type 1 (HIV-1) infection in adults who are virologically suppressed (HIV-1 RNA < 50 copies/mL) on a stable antiretroviral regimen without present or past evidence of viral resistance to, and no prior virological failure with agents of the NNRTI and INI class for:

    - oral lead in to assess tolerability of Vocabria and rilpivirine prior to administration of long acting cabotegravir injection plus long acting rilpivirine injection.

    - oral therapy for adults who will miss planned dosing with cabotegravir injection plus rilpivirine injection.

    Vocabria injection is indicated, in combination with rilpivirine injection, for the treatment of Human Immunodeficiency Virus type 1 (HIV-1) infection in adults who are virologically suppressed (HIV-1 RNA < 50 copies/mL) on a stable antiretroviral regimen without present or past evidence of viral resistance to, and no prior virological failure with agents of the NNRTI and INI class.

    Treatment of human immunodeficiency virus (HIV-1) infection

    Prevention of human immunodeficiency virus (HIV-1) infection

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cabotegravir is an inhibitor of HIV integrase, which reduces viral replication. It has a long duration of action as the oral tablet is given daily and the intramuscular suspension is given monthly. Patients should be counselled regarding the risk of hypersensitivity, hepatotoxicity, and depression.

    5.2 MeSH Pharmacological Classification

    HIV Integrase Inhibitors

    Inhibitors of HIV INTEGRASE, an enzyme required for integration of viral DNA into cellular DNA. (See all compounds classified as HIV Integrase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    CABOTEGRAVIR
    5.3.2 FDA UNII
    HMH0132Z1Q
    5.3.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Organic Anion Transporter 3 Inhibitors
    5.4 ATC Code

    J05AX

    J - Antiinfectives for systemic use

    J05 - Antivirals for systemic use

    J05A - Direct acting antivirals

    J05AJ - Integrase inhibitors

    J05AJ04 - Cabotegravir

    5.5 Absorption, Distribution and Excretion

    Absorption

    Oral cabotegravir has a Tmax of 3 hours, reaches a Cmax of 8.0 g/mL, and has an AUC of 145 g\*h/mL. Intramuscular extended-release cabotegravir has a Tmax of 7 days, reaches a Cmax of 8.0 g/mL, and has an AUC of 1591 g\*h/mL.

    Route of Elimination

    An oral radiolabelled dose of cabotegravir is 58.5% recovered in the feces and 26.8% recovered in the urine.

    Volume of Distribution

    Data regarding the volume of distribution of cabotegravir is not readily available.

    Clearance

    Data regarding the clearance of cabotegravir is not readily available. Clearance in dogs was 0.34 mL/min/kg and in cynomolgus monkeys was 0.32 mL/min/kg.

    5.6 Metabolism/Metabolites

    Cabotegravir is O-glucuronidated to the M1 and M2 metabolites, with 67% of glucuronidation performed by UGT1A1, and 33% by UGT1A9.

    5.7 Biological Half-Life

    The mean half life of oral cabotegravir is 41 hours. The mean half life of intramuscular extended-release cabotegravir is 5.6-11.5 weeks.

    5.8 Mechanism of Action

    Cabotegravir binds to the active site of HIV integrase, preventing strand transfer of the viral genome into the host genome, and preventing replication of the virus.