Elvitegravir

Elvitegravir
Clinical data
Trade names	Vitekta; Stribild (fixed-dose combination)
Other names	GS-9137
License data	EU EMA: by INN;
Routes of; administration	By mouth
ATC code	J05AJ02 (WHO) ;
Pharmacokinetic data
Protein binding	98%
Metabolism	liver, via CYP3A
Elimination half-life	12.9 (8.7–13.7) hours
Excretion	liver 93%, renal 7%
Identifiers
	IUPAC name 6-[(3-Chloro-2-fluorophenyl)methyl]-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxoquinoline-3-carboxylic acid;
CAS Number	697761-98-1 ;
PubChem CID	5277135;
DrugBank	DB09101 ;
ChemSpider	4441060 ;
UNII	4GDQ854U53;
KEGG	D06677 ;
ChEBI	CHEBI:72289 ;
ChEMBL	ChEMBL204656 ;
NIAID ChemDB	241767;
CompTox Dashboard (EPA)	DTXSID101021650 ;
Chemical and physical data
Formula	C23H23ClFNO5
Molar mass	447.89 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1cccc(c1F)Cc3c(OC)cc2c(C(=O)\C(=C/N2[C@H](CO)C(C)C)C(=O)O)c3;
	InChI InChI=1S/C23H23ClFNO5/c1-12(2)19(11-27)26-10-16(23(29)30)22(28)15-8-14(20(31-3)9-18(15)26)7-13-5-4-6-17(24)21(13)25/h4-6,8-10,12,19,27H,7,11H2,1-3H3,(H,29,30)/t19-/m1/s1 ; Key:JUZYLCPPVHEVSV-LJQANCHMSA-N ;
	(what is this?) (verify)

Elvitegravir (EVG) is an integrase inhibitor used to treat HIV infection. It was developed^[1] by the pharmaceutical company Gilead Sciences, which licensed EVG from Japan Tobacco in March 2008.^[2]^[3]^[4] The drug gained approval by the U.S. Food and Drug Administration on 27 August 2012, for use in adult patients starting HIV treatment for the first time as part of the fixed dose combination known as Stribild.^[5] On 24 September 2014, the FDA approved Elvitegravir as a single pill formulation under the trade name Vitekta.^[6] On 5 November 2015, the FDA approved the drug for use in patients affected with HIV-1 as a part of a second fixed dose combination pill known as Genvoya.^[7]

According to the results of the phase II clinical trial, patients taking once-daily elvitegravir boosted by ritonavir had greater reductions in viral load after 24 weeks compared to individuals randomized to receive a ritonavir-boosted protease inhibitor.^[8]

^ "Phase III Clinical Trial of Elvitegravir". Gilead Press Release. 22 July 2008. Archived from the original on 8 February 2013.
^ "Gilead and Japan Tobacco Sign Licensing Agreement for Novel HIV Integrase Inhibitor". Gilead Press Release. 22 March 2008. Archived from the original on 8 February 2013.
^ Shimura K, Kodama E, Sakagami Y, Matsuzaki Y, Watanabe W, Yamataka K, et al. (January 2008). "Broad antiretroviral activity and resistance profile of the novel human immunodeficiency virus integrase inhibitor elvitegravir (JTK-303/GS-9137)". Journal of Virology. 82 (2): 764–774. doi:10.1128/JVI.01534-07. PMC 2224569. PMID 17977962.{{cite journal}}: CS1 maint: overridden setting (link)
^ Stellbrink HJ (October 2007). "Antiviral drugs in the treatment of AIDS: what is in the pipeline ?". European Journal of Medical Research. 12 (9): 483–495. PMID 17933730.
^ Sax PE, DeJesus E, Mills A, Zolopa A, Cohen C, Wohl D, et al. (June 2012). "Co-formulated elvitegravir, cobicistat, emtricitabine, and tenofovir versus co-formulated efavirenz, emtricitabine, and tenofovir for initial treatment of HIV-1 infection: a randomised, double-blind, phase 3 trial, analysis of results after 48 weeks". Lancet. 379 (9835): 2439–2448. doi:10.1016/S0140-6736(12)60917-9. PMID 22748591. S2CID 24183976.{{cite journal}}: CS1 maint: overridden setting (link)
^ "FDA Approval Bulletin". U.S. Food & Drug Administration (FDA). Archived from the original on 3 November 2014.
^ "Press Announcements - FDA approves new treatment for HIV". www.fda.gov. Archived from the original on 6 November 2015. Retrieved 10 January 2016.
^ Thaczuk D, Carter M (19 September 2007). "ICAAC: Best response to elvitegravir seen when used with T-20 and other active agents". Aidsmap.com. Archived from the original on 2 January 2010.

[1] "Phase III Clinical Trial of Elvitegravir". Gilead Press Release. 22 July 2008. Archived from the original on 8 February 2013.

[2] "Gilead and Japan Tobacco Sign Licensing Agreement for Novel HIV Integrase Inhibitor". Gilead Press Release. 22 March 2008. Archived from the original on 8 February 2013.

[3] Shimura K, Kodama E, Sakagami Y, Matsuzaki Y, Watanabe W, Yamataka K, et al. (January 2008). "Broad antiretroviral activity and resistance profile of the novel human immunodeficiency virus integrase inhibitor elvitegravir (JTK-303/GS-9137)". Journal of Virology. 82 (2): 764–774. doi:10.1128/JVI.01534-07. PMC 2224569. PMID 17977962.{{cite journal}}: CS1 maint: overridden setting (link)

[4] Stellbrink HJ (October 2007). "Antiviral drugs in the treatment of AIDS: what is in the pipeline ?". European Journal of Medical Research. 12 (9): 483–495. PMID 17933730.

[5] Sax PE, DeJesus E, Mills A, Zolopa A, Cohen C, Wohl D, et al. (June 2012). "Co-formulated elvitegravir, cobicistat, emtricitabine, and tenofovir versus co-formulated efavirenz, emtricitabine, and tenofovir for initial treatment of HIV-1 infection: a randomised, double-blind, phase 3 trial, analysis of results after 48 weeks". Lancet. 379 (9835): 2439–2448. doi:10.1016/S0140-6736(12)60917-9. PMID 22748591. S2CID 24183976.{{cite journal}}: CS1 maint: overridden setting (link)

[6] "FDA Approval Bulletin". U.S. Food & Drug Administration (FDA). Archived from the original on 3 November 2014.

[7] "Press Announcements - FDA approves new treatment for HIV". www.fda.gov. Archived from the original on 6 November 2015. Retrieved 10 January 2016.

[8] Thaczuk D, Carter M (19 September 2007). "ICAAC: Best response to elvitegravir seen when used with T-20 and other active agents". Aidsmap.com. Archived from the original on 2 January 2010.

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