Bictegravir

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]

Bictegravir
Identifiers
IUPAC name
  • (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
Chemical and physical data
FormulaC21H18F3N3O5
Molar mass449.386 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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

Medical use

Bictegravir is used a in fixed dose combination with tenofovir alafenaminde 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]

References
  1. "Recommended INN: List 75" (PDF). WHO Drug Information. 30 (1): 102. 2016.
  2. "Bictegravir - Gilead Sciences". Adis Insight. Springer Nature Switzerland AG. Retrieved 22 January 2017.
  3. Highleyman L (6 July 2016). "New integrase inhibitor bictegravir looks promising in early studies". NAM aidsmap.
  4. Zeuli, J; Rizza, S; Bhatia, R; Temesgen, Z (2019-11-01). "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. ISSN 1699-4019. PMID 31840682. S2CID 209385285.
  5. "Press Release: Gilead Presents Preliminary Data on Bictegravir, an Investigational Integrase Strand Transfer Inhibitor for the Treatment of HIV | Gilead". Gilead. June 20, 2016.
  6. "U.S. Food and Drug Administration Approves Gilead's Biktarvy (Bictegravir, Emtricitabine, Tenofovir Alafenamide) for Treatment of HIV-1 Infection" (Press release). Gilead. February 7, 2018.
  7. Wohl, David A.; Yazdanpanah, Yazdan; Baumgarten, Axel; Clarke, Amanda; Thompson, Melanie A.; Brinson, Cynthia; Hagins, Debbie; Ramgopal, Moti N.; Antinori, Andrea; Wei, Xuelian; Acosta, Rima (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. ISSN 2352-3018. PMID 31068270. S2CID 148570850.
  8. "Biktarvy - FDA Prescribing Highlights" (PDF).

Further reading
  • "Bictegravir". Drug Information Portal. U.S. National Library of Medicine.
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