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Cabotegravir Sodium

Cabotegravir Sodium

Synopsis, Chemistry

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Also known as: 1051375-13-3, Gsk1265744b, Gsk-1265744b, Vocabria, S-265744b, Cabotegravir sodium [usan]

Molecular Formula

C₁₉H₁₆F₂N₃NaO₅

Molecular Weight

427.3 g/mol

InChI Key

AEZBWGMXBKPGFP-KIUAEZIZSA-M

FDA UNII

3L12PT535M

1 2D Structure

Cabotegravir Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(3R,6S)-12-[(2,4-difluorophenyl)methylcarbamoyl]-6-methyl-8,11-dioxo-4-oxa-1,7-diazatricyclo[7.4.0.03,7]trideca-9,12-dien-10-olate

2.1.2 InChI

InChI=1S/C19H17F2N3O5.Na/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);/q;+1/p-1/t9-,14+;/m0./s1

2.1.3 InChI Key

AEZBWGMXBKPGFP-KIUAEZIZSA-M

2.1.4 Canonical SMILES

CC1COC2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)[O-].[Na+]

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-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

3L12PT535M

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

4. Cabotegravir Extended-release Injectable Suspension

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. 1051375-13-3

2. Gsk1265744b

3. Gsk-1265744b

4. Vocabria

5. S-265744b

6. Cabotegravir Sodium [usan]

7. Cabotegravir (sodium)

8. S 265744b

9. 3l12pt535m

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

11. 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-, Sodium Salt (1:1), (3s,11ar)-

12. 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

13. Unii-3l12pt535m

14. Chembl3137330

15. Cabotegravir Sodium (jan/usan)

16. Cabotegravir Sodium [jan]

17. Chebi:172948

18. Amy30044

19. Cabotegravir Sodium [who-dd]

20. Gsk 1265744b

21. Hy-15592a

22. Cabotegravir Sodium [orange Book]

23. Ac-30853

24. Cs-0007799

25. D10549

26. F11513

27. A935003

28. Q27257476

29. (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, Sodium Salt

30. 1229006-16-9

31. Sodium (3s,11ar)-8-[(2,4-difluorobenzyl)carbamoyl]-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-olate

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

2.4 Create Date

2010-07-06

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₆F₂N₃NaO₅
Molecular Weight	427.3 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Exact Mass	427.09557123 g/mol
Monoisotopic Mass	427.09557123 g/mol
Topological Polar Surface Area	102 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	820
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	2

4 Drug and Medication Information

4.1 Drug Indication

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.

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Human Immunodeficiency Virus Integrase Strand Transfer Inhibitor [EPC]; Organic Anion Transporter 1 Inhibitors [MoA]; Organic Anion Transporter 3 Inhibitors [MoA]; HIV Integrase Inhibitors [MoA]

5.3 ATC Code

J05AX