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]

Bictegravir

Clinical data
Other names	GS-9883
ATC code	None
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 as salt: 1807988-02-8
PubChem CID	90311989
DrugBank	DB11799 as salt: DBSALT002077
ChemSpider	44208822 as salt: 48772870
UNII	8GB79LOJ07 as salt: 4L5MP1Y7W7
KEGG	D10909 as salt: D10910
ChEBI	CHEBI:172943
ChEMBL	ChEMBL3989866 as salt: ChEMBL3989867
CompTox Dashboard (EPA)	DTXSID701027937
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

The combination drug bictegravir/emtricitabine/tenofovir alafenamide (Biktarvy) was approved for use in 2018 in Australia,^[6] the European Union^[7] and the United States^[8] and in 2019 in New Zealand^[9] and the United Kingdom;^[10] a generic version was approved by the Drugs Controller General of India in 2019.^[11] As of 2024,^[update] it is recommended as a first-line choice of antiretroviral therapy in several countries, including the European Union,^[12] the United Kingdom^[13] and the United States.^[14]

Medical use

Bictegravir is used a in fixed dose combination with tenofovir alafenamide and emtricitabine for the treatment of HIV-1 infection.^[4][15]

Contraindication

Bictegravir should not be used with dofetilide and rifampin.^[16] Use of dofetilide with bictegravir increases the concentration of dofetilide, which can lead to life-threatening events.^[16] Concomitant use of bictegravir and rifampin causes significant interactions because of an effect rifampin has on bictegravir.^[16] 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.^[17][18]