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Bictegravir

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Chemistry

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Also known as: 1611493-60-7, Gs-9883, Bictegravir [inn], Gs-9883-01, (2r,5s,13ar)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide, 8gb79loj07

Molecular Formula

C₂₁H₁₈F₃N₃O₅

Molecular Weight

449.4 g/mol

InChI Key

SOLUWJRYJLAZCX-LYOVBCGYSA-N

FDA UNII

8GB79LOJ07

Bictegravir is a recently approved investigational drug that has been used in trials studying the treatment of HIV-1 and HIV-2 infection. It has been approved for HIV-1 monotherapy combined with 2 other antiretrovirals in a single tablet.

1 2D Structure

Bictegravir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,11R,13R)-5-hydroxy-3,6-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-12-oxa-2,9-diazatetracyclo[11.2.1.02,11.04,9]hexadeca-4,7-diene-7-carboxamide

2.1.2 InChI

InChI=1S/C21H18F3N3O5/c22-9-3-14(23)12(15(24)4-9)6-25-20(30)13-7-26-8-16-27(10-1-2-11(5-10)32-16)21(31)17(26)19(29)18(13)28/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30)/t10-,11+,16+/m0/s1

2.1.3 InChI Key

SOLUWJRYJLAZCX-LYOVBCGYSA-N

2.1.4 Canonical SMILES

C1CC2CC1N3C(O2)CN4C=C(C(=O)C(=C4C3=O)O)C(=O)NCC5=C(C=C(C=C5F)F)F

2.1.5 Isomeric SMILES

C1C[C@@H]2C[C@H]1N3[C@H](O2)CN4C=C(C(=O)C(=C4C3=O)O)C(=O)NCC5=C(C=C(C=C5F)F)F

2.2 Other Identifiers

2.2.1 UNII

8GB79LOJ07

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bictegravir Sodium

2. Gs-9883

3. Gs-9883 Sodium

4. Gs-9883-01

5. Gs-9883-01 Sodium

2.3.2 Depositor-Supplied Synonyms

1. 1611493-60-7

2. Gs-9883

3. Bictegravir [inn]

4. Gs-9883-01

5. (2r,5s,13ar)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide

6. 8gb79loj07

7. (1s,11r,13r)-5-hydroxy-3,6-dioxo-n-[(2,4,6-trifluorophenyl)methyl]-12-oxa-2,9-diazatetracyclo[11.2.1.02,11.04,9]hexadeca-4,7-diene-7-carboxamide

8. 2,5-methanopyrido(1',2':4,5)pyrazino(2,1-b)(1,3)oxazepine-10-carboxamide, 2,3,4,5,7,9,13,13a-octahydro-8-hydroxy-7,9-dioxo-n-((2,4,6-trifluorophenyl)methyl)-, (2r,5s,13ar)-

9. Bictegravir [usan:inn]

10. Bictegravirum

11. Unii-8gb79loj07

12. Gs 9883

13. Bictegravir [mi]

14. Bictegravir (usan/inn)

15. Bictegravir [usan]

16. Bictegravir [who-dd]

17. Chembl3989866

18. Schembl15914278

19. Gtpl11575

20. Chebi:172943

21. Bdbm330048

22. Dtxsid701027937

23. Amy12383

24. Bcp25703

25. Ex-a3161

26. Gs9883

27. S5911

28. Db11799

29. Dt-0020

30. Ac-30658

31. Hy-17605

32. Cs-0014685

33. D10909

34. N16998

35. Us9663528, 42

36. A902376

37. Q27270406

38. Gs-9883; Gs 9883; Gs9883; Gs-9883-01

39. (1s,11r,13r)-5-hydroxy-3,6-dioxo-n-[(2,4,6-trifluorophenyl)methyl]-12-oxa-2,9-diazatetracyclo[11.2.1.0(2),(1)(1).0?,?]hexadeca-4,7-diene-7-carboxamide

40. (2r,5s,13ar)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2, 1-b][1,3]oxazepine-10-carboxamide

2.4 Create Date

2015-02-13

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₈F₃N₃O₅
Molecular Weight	449.4 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	449.11985517 g/mol
Monoisotopic Mass	449.11985517 g/mol
Topological Polar Surface Area	99.2 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	912
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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

Bictegravir is indicated in the management of HIV-1 infection in patients not previously treated with antiretroviral therapy. Additionally, Bictegravir is indicated in the management of HIV-1 infection in patients who are virologically suppressed (HIV-1 RNA <50 c/mL) on a regular antiretroviral regimen for a minimum of three months without a history of failure in treatment and no known factors associated with the resistance to the individual components of the medication. It is used in combination with tenofovir and emtricitabine.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bictegravir is an HIV-1 integrase strand transfer inhibitor (INSTI). Bictegravir (BIC) inhibits HIV-1 virus replication into the human genome. It can be taken once daily without additional dosing. Bictegravir (BIC) inhibits strand transfer of viral DNA into the host genome and thereby prevents HIV-1 replication.

5.2 Absorption, Distribution and Excretion

Absorption

Bictegravir is rapidly absorbed within the body. Tmax= 2.0-4.0h [FDA LABEL, 1219]

Route of Elimination

BIC is mainly eliminated through UGT1A1 glucuronidation and CYP3A4 oxidation, equally. About 1% of the bictegravir dose is excreted in the urine, unchanged [1218,1219].

Volume of Distribution

0.2 L/Kg in humans

Clearance

Bictegravir is mainly cleared by the kidneys. Those with renal clearance <30 should not take bictegravir [FDA LABEL]

5.3 Metabolism/Metabolites

In a 10-day dose-ranging study, monotherapy (5 mg to 100 mg) once daily in adults who were not previously treated with bictegravir, the median half-life of BIC ranged from 15.9 h - 20.9 h [L1219. Bictegravir is metabolized in the liver and kidneys. CYP3A4 and UGT1A are the primary enzymes involved in the metabolism of bictegravir. Administration of bictegravir is not advised in patients with renal creatinine clearance of <30 mL/min and patients with hepatic disease [FDA LABEL].

5.4 Biological Half-Life

17. 3h [FDA LABEL, L1219]

5.5 Mechanism of Action

This single dose medication inhibits the strand transfer of viral DNA into the human genome, preventing HIV-1 virus replication and propagation. In vitro, bictegravir has shown powerful antiviral activity against HIV-2 and various subtypes of HIV-1. It has shown synergistic effects when combined with other ARVs, including tenofovir alafenamide (TAF), emtricitabine (FTC), and darunavir (DRV) [FDA LABEL]. The three components of the first USA approved medication ( trade name: Biktarvy ) are as follows: Bictegravir: integrase strand transfer inhibitor; INSTI), an HIV-1 encoded enzyme necessary for viral replication. Inhibition of the integrase enzyme prevents the integration of HIV-1 into host DNA, blocking the conversion of the HIV-1 provirus and progression of the virus [FDA LABEL]. Emtricitabine: FTC, is phosphorylated by cellular enzymes to form emtricitabine 5'-triphosphate. Emtricitabine is phosphorylated to form emtricitabine 5'-triphosphate intracellularly. This metabolite inhibits the activity of human immunodeficiency virus (HIV) reverse transcriptase by competing with the substrate deoxycytidine 5'-triphosphate and by incorporating itself into viral DNA preventing DNA chain elongation [FDA LABEL]. Tenofovir Alafenamide: TAF is a phosphonamidate prodrug of tenofovir (2-deoxyadenosine monophosphate analog). Plasma exposure to TAF leads to leakage into cells and then TAF is intracellularly converted to tenofovir by hydrolysis by cathepsin. Tenofovir is subsequently phosphorylated by cellular kinases to the metabolite tenofovir diphosphate, which is the active form of the drug. Tenofovir diphosphate inhibits HIV-1 replication by incorporating into viral DNA by the HIV reverse transcriptase, resulting in DNA chain-termination. Tenofovir diphosphate also weakly inhibits mammalian DNA polymerases [FDA LABEL].

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