Bictegravir

Bictegravir (INN; BIC, formerly known as GS-9883)[1][2] is an antiviral drug of the integrase inhibitor 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] 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[4] and the combination drug bictegravir/emtricitabine/tenofovir alafenamide (Biktarvy) was approved for use in the United States in 2018.[5]

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	1611493-60-7
PubChem CID	90311989
ChemSpider	44208822
UNII	8GB79LOJ07
KEGG	D10909
Chemical and physical data
Formula	C21H18F3N3O5
Molar mass	449.386 g·mol^−1
3D model (JSmol)	Interactive image
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

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. "Press Release: Gilead Presents Preliminary Data on Bictegravir, an Investigational Integrase Strand Transfer Inhibitor for the Treatment of HIV | Gilead". Gilead. June 20, 2016.
5. "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.

Further reading

• Tsiang M, Jones GS, Goldsmith J, Mulato A, Hansen D, Kan E, et al. (December 2016). "Antiviral Activity of Bictegravir (GS-9883), a Novel Potent HIV-1 Integrase Strand Transfer Inhibitor with an Improved Resistance Profile". Antimicrobial Agents and Chemotherapy. 60 (12): 7086–7097. doi:10.1128/AAC.01474-16. PMC 5118987. PMID 27645238.