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Cabotegravir

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Synopsis

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Chemistry

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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

Cabotegravir

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 Formula	C₁₉H₁₇F₂N₃O₅
Molecular Weight	405.4 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Exact Mass	405.11362698 g/mol
Monoisotopic Mass	405.11362698 g/mol
Topological Polar Surface Area	99.2 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	814
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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

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