Bictegravir
Clinical data
Other namesGS-9883
ATC code
  • None
Identifiers
  • (1S,11R,13R)-5-Hydroxy-3,6-dioxo-N-(2,4,6-trifluorobenzyl)-12-oxa-2,9-diazatetracyclo[11.2.1.0~2,11~.0~4,9~]hexadeca-4,7-diene-7-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC21H18F3N3O5
Molar mass449.386 g·mol−1
3D model (JSmol)
  • c1c(cc(c(c1F)CNC(=O)c2cn3c(c(c2=O)O)C(=O)N4[C@H]5CC[C@H](C5)O[C@@H]4C3)F)F
  • 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
  • Key:SOLUWJRYJLAZCX-LYOVBCGYSA-N

Bictegravir (INN; BIC, formerly known as GS-9883)[1][2] is a second-generation integrase inhibitor (INSTI) class that was structurally derived from an earlier compound dolutegravir by scientists at Gilead Sciences. In vitro and clinical results were presented by Gilead in the summer of 2016.[3][4] In 2016, bictegravir was in a Phase 3 trial as part of a single tablet regimen in combination with tenofovir alafenamide (TAF) and emtricitabine (FTC) for the treatment of HIV-1 infection[5] and the combination drug bictegravir/emtricitabine/tenofovir alafenamide (Biktarvy) was approved for use in the United States in 2018.[6]

Medical use

Bictegravir is used a in fixed dose combination with tenofovir alafenamide and emtricitabine for the treatment of HIV-1 infection.[4][7]

Contraindication

Bictegravir should not be used with dofetilide and rifampin.[8] Use of dofetilide with bictegravir increases the concentration of dofetilide, which can lead to life-threatening events.[8] Concomitant use of bictegravir and rifampin causes significant interactions because of an effect rifampin has on bictegravir.[8] Bictagravir is metabolized primarily through the liver (CYP3A4), so inducers of CYP3A4 should be avoided.[4]

Adverse effects

The most common side effects seen in bictegravir use include diarrhea, nausea, and headache.[4]

Society and culture

Economics

In February 2022, Gilead agreed to pay ViiV Healthcare over $1 billion to settle patent infringement cases.[9][10]

References

  1. ↑ "Recommended INN: List 75" (PDF). WHO Drug Information. 30 (1): 102. 2016. Archived (PDF) from the original on 4 November 2021. Retrieved 4 October 2020.
  2. ↑ "Bictegravir - Gilead Sciences". Adis Insight. Springer Nature Switzerland AG. Archived from the original on 2 February 2017. Retrieved 22 January 2017.
  3. ↑ Highleyman L (6 July 2016). "New integrase inhibitor bictegravir looks promising in early studies". NAM aidsmap. Archived from the original on 2 February 2017. Retrieved 20 January 2017.
  4. 1 2 3 4 Zeuli J, Rizza S, Bhatia R, Temesgen Z (November 2019). "Bictegravir, a novel integrase inhibitor for the treatment of HIV infection". Drugs of Today. 55 (11): 669–682. doi:10.1358/dot.2019.55.11.3068796. PMID 31840682. S2CID 209385285. Archived from the original on 28 August 2023. Retrieved 28 August 2023.
  5. ↑ "Press Release: Gilead Presents Preliminary Data on Bictegravir, an Investigational Integrase Strand Transfer Inhibitor for the Treatment of HIV | Gilead". Gilead. 20 June 2016. Archived from the original on 2 February 2017. Retrieved 20 January 2017.
  6. ↑ "U.S. Food and Drug Administration Approves Gilead's Biktarvy (Bictegravir, Emtricitabine, Tenofovir Alafenamide) for Treatment of HIV-1 Infection" (Press release). Gilead. 7 February 2018.
  7. ↑ Wohl DA, Yazdanpanah Y, Baumgarten A, Clarke A, Thompson MA, Brinson C, et al. (June 2019). "Bictegravir combined with emtricitabine and tenofovir alafenamide versus dolutegravir, abacavir, and lamivudine for initial treatment of HIV-1 infection: week 96 results from a randomised, double-blind, multicentre, phase 3, non-inferiority trial". The Lancet. HIV. 6 (6): e355–e363. doi:10.1016/S2352-3018(19)30077-3. PMID 31068270. S2CID 148570850. Archived from the original on 29 January 2022. Retrieved 29 January 2022.{{cite journal}}: CS1 maint: overridden setting (link)
  8. 1 2 3 "Biktarvy - FDA Prescribing Highlights" (PDF). Archived (PDF) from the original on 26 July 2021. Retrieved 29 January 2022.
  9. ↑ "GSK announces settlement between ViiV Healthcare and Gilead Sciences, Inc. resolving litigation relating to Biktarvy and ViiV's dolutegravir patents and entry into a patent licence agreement". ViiV Healthcare (Press release). ViiV Healthcare. Retrieved 26 August 2023.
  10. ↑ "GSK announces settlement between ViiV Healthcare and Gilead Sciences, Inc. resolving litigation relating to Biktarvy and ViiV's dolutegravir patents and entry into a patent licence agreement". GSK US (Press release). 1 February 2022. Retrieved 28 August 2023.

Further reading


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