Bictegravir

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;
DrugBank	DB11799;
ChemSpider	44208822;
UNII	8GB79LOJ07;
KEGG	D10909;
ChEBI	CHEBI:172943;
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;

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 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), thus 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[]

^ "Recommended INN: List 75" (PDF). WHO Drug Information. 30 (1): 102. 2016.
^ "Bictegravir - Gilead Sciences". Adis Insight. Springer Nature Switzerland AG. Retrieved 22 January 2017.
^ Highleyman L (6 July 2016). "New integrase inhibitor bictegravir looks promising in early studies". NAM aidsmap.
^ ^a ^b ^c ^d 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.
^ "Press Release: Gilead Presents Preliminary Data on Bictegravir, an Investigational Integrase Strand Transfer Inhibitor for the Treatment of HIV | Gilead". Gilead. June 20, 2016.
^ "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.
^ 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.
^ ^a ^b ^c "Biktarvy - FDA Prescribing Highlights" (PDF).

External links[]

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

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[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.

[:1-4] 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.

[:0-8] "Biktarvy - FDA Prescribing Highlights" (PDF).

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