emtricitabine

Trade name: emtriva

Small moleculeapprovedCOVID-19Fast Track ^FDA

Approved

Jul 2, 2003

Emtricitabine was discovered by Emory researchers Dr. Dennis C. Liotta, Dr. Raymond F. Schinazi and Dr. Woo-Baeg Choi and licensed to Triangle Pharmaceuticals by Emory University in 1996. Triangle was acquired by Gilead in 2003. Emtricitabine, marketed by Gilead as Emtriva, was first approved by the U.S. Food and Drug Administration in July 2003 for the treatment of HIV infection in combination with other antiretroviral agents. Emtricitabine, a synthetic nucleoside analog of cytidine, is phosphorylated by cellular enzymes to form emtricitabine 5'-triphosphate. Emtricitabine 5'-triphosphate inhibits the activity of the HIV-1 reverse transcriptase by competing with the natural substrate deoxycytidine 5'-triphosphate and by being incorporated into nascent viral DNA which results in chain termination. — NCATS

Clinical trial activity

521 trials · 370 clinical orgs · 19 marketing orgs

Phase 1

Phase 2

235

Phase 3

159

Phase 4

170

Earliest trial started Feb 1, 1999 (NCT00196599)

Timeline

1990s

Jan 1, 1994
Burroughs Wellcome — IND Organization
Jan 1, 1994
Burroughs Wellcome — IND Organization
Jan 1, 1999
Earliest Phase 1 Sponsor(trial)
Jan 1, 1999
Earliest Phase 2 Sponsor(trial)
Jan 1, 1999
Earliest Phase 3 Sponsor(trial)

2000s

Jul 2, 2003
Gilead Sciences — Earliest FDA Approval
Jul 2, 2003
Gilead Sciences — NDA Organization
Jul 12, 2006
Gilead Sciences — Marketing Organization
Dec 23, 2008
Matrix Laboratories Limited — Marketing Organization

2010s

Jul 31, 2013
Strides Pharma Science — Marketing Organization
Sep 12, 2014
Mylan — Marketing Organization
Sep 12, 2014
Mylan — NDA Secondary Org
Nov 28, 2014
Macleods Pharmaceuticals, Ltd — Marketing Organization
Jun 8, 2017
Teva — Marketing Organization
Mar 23, 2018
Aurobindo Pharma — Marketing Organization
Apr 9, 2018
PHARMOBEDIENT — Marketing Organization
Jul 2, 2018
Cipla — Marketing Organization
Jul 17, 2018
Johnson and Johnson — Marketing Organization
Jul 17, 2018
Johnson and Johnson — NDA Secondary Org
Aug 22, 2018
Amneal Pharmaceuticals — Marketing Organization
Jul 26, 2019
Laurus Labs Ltd — Marketing Organization

2020s

Feb 28, 2020
Zydus Discovery DMCC — Marketing Organization
May 15, 2020
Neogen — Marketing Organization
Jun 4, 2021
Lupin — Marketing Organization
Jun 4, 2021
Chartwell Pharmaceuticals — Marketing Organization
Jun 16, 2021
Apotex — Marketing Organization
Oct 7, 2021
Hetero Labs Ltd — Marketing Organization
May 26, 2023
Aurobindo Pharma — NDA Secondary Org
Jul 18, 2023
Lupin — NDA Secondary Org

Indications

Approved for

HIV Infections

Studied for

Mechanism of action

Human immunodeficiency virus type 1 reverse transcriptaseINHIBITOR
Q72547 inhibitor
- Reverse transcriptase/RNaseH (Q72547) ↗

Combination products

atripla
with efavirenz, tenofovir
Also known as emtricitabine; tenofovir disoproxil fumarate; efavirenz
biktarvy
with bictegravir, tenofovir alafenamide
Also known as bictegravir, embitcitabine, tenofovir alafenamide, bictegravir/emtricitabine/tenofovir alafenamide 50/200/25 mg
complera
with tenofovir, rilpivirine
descovy
with tenofovir alafenamide
genvoya
with tenofovir alafenamide, cobicistat, elvitegravir
Also known as elvitegravir, cobicistat, emtricitabine, and tenofovir alafenamide
odefsey
with tenofovir alafenamide, rilpivirine
stribil
with tenofovir, cobicistat, elvitegravir
Also known as cobicistat, elvitegravir, emtricitabine, and tenofovir disoproxil fumarate
symtuza
with darunavir, tenofovir alafenamide, cobicistat
truvada
with tenofovir
Also known as emtricitabine and tenofovir disoproxil fumarate, emtricitabine/tenofovir disoproxil fumarate 200 mg-245 mg oral tablet [truvada], immediate intervention arm truvada in brazil, tenofovir (300mg)/emtricitabine(200mg) [truvada®], tenofovir disoproxil fumarate; emtricitabine, tenofovir disoproxyl fumarate 300 mg plus emtricitabine 200 mg oral tablet

Approval history

approvedFast trackJul 2, 2003

Chemistry & pharmacology

Loading structure…

SMILES

NC1=NC(=O)N(C=C1F)[C@@H]2CS[C@H](CO)O2

Mol. weight: 247.247 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Single Stereoisomer
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Prescription Only

Oral

Yes

Parenteral

Topical

Black box warningProdrug

Sources

Also known as

1-(2-(hydroxymethyl)oxathiolan-5-yl)-5-fluorocytosine
2',3',5-ftc
2',3'-dideoxy-5-fluoro-3'-thiacytidine
2',3'-dideoxy-5-fluoro-3'-thiacytidine, (2s-cis)-isomer
2'-deoxy-5-fluoro-3'-oxa-4'-thiocytidine
(-)-2'-deoxy-5-fluoro-3'-thiacytidine
(-)-2'-deoxy-5-fluoro-3'-thiacytidine
(-)-2'-deoxy-5-fluoro-3'-thiacytidine
2'-deoxy-5-fluoro-3'-thiacytidine
2'-deoxy-5-fluoro-3'-thiacytidine, 2s-trans isomer
2'-deoxy-5-fluoro-3'-thiacytidine, cis-isomer
2-ftc
(-)-(2r,5s)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
(-)-(2r,5s)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
(2r-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1h)-pyrimidinone
(2r-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1h)-pyrimidinone
4-amino-5-fluoro-1-((2r,5s)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1h-pyrimidin-2-one
4-amino-5-fluoro-1-((2r,5s)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1h-pyrimidin-2-one
4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one
4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one
524w91
524w91
524w91
5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
(-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine
(-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine
bw524w91
bw 524w91
bw-524w91
bw-524w91
bw-524w91
(-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1h)-pyrimidin-2-one
(-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1h)-pyrimidin-2-one
coviracil
descovy
dotfc
efavirenz / emtricitabine / tenofovir disoproxil fumarate
efavirenz / emtricitabine / tenofovir disoproxil maleate
efavirenz / emtricitabine / tenofovir disoproxil, phosphate
efavirenz / emtricitabine / tenofovir disoproxil succinate
elvitegravir / cobicistat / emtricitabine / tenofovir disoproxil fumarate
emtricitabin
emtricitabin
emtricitabina
emtricitabina
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine
emtricitabine / rilpivirine hydrochloride / tenofovir alafenamide
emtricitabine / rilpivirine hydrochloride /tenofovir disoproxil fumarate
emtricitabine / tenofovir
emtricitabine / tenofovir alafenamide
emtricitabine / tenofovir disoproxil fumarate
emtricitabine / tenofovir disoproxil maleate
emtricitabine, tenofovir disoproxil phosphate
emtricitabine / tenofovir disoproxil succinate
emtricitabinum
emtricitabinum
emtricitabline
emtricitagine
emtriva
emtriva
emtriva
emtriva
emtriva
ftc
ftc
(-)-ftc
(-)-ftc
(-)-ftc
ftc-(-)
ftc-(-)
racivir

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT07202546	Phase 2	Nov 28, 2025	ViiV Healthcare
NCT07071623	Phase 3	Nov 10, 2025	Merck
NCT06908252	Phase 4	Sep 17, 2025	Duke University, National Institute of Allergy and Infectious Diseases (NIAID)
NCT07055451	Phase 1	Aug 12, 2025	Gilead Sciences
NCT07044297	Phase 3	Jul 31, 2025	Merck
NCT07075146	Phase 3	May 5, 2025	Instituto Mexicano del Seguro Social
NCT06891066	Phase 2	Apr 14, 2025	Merck
NCT07031063	Phase 4	Apr 1, 2025	Instituto Mexicano del Seguro Social
NCT06830668	Phase 4	Feb 28, 2025	Gilead Sciences, Government of China
NCT06816043	Phase 1	Feb 21, 2025	Merck
NCT06203132	Phase 3	Nov 30, 2024	Assistance Publique - Hôpitaux de Paris, European and Developing Countries Clinical Trials Partnership (EDCTP), Government of France, Merck
NCT06560684	Phase 2	Oct 29, 2024	National Institute of Allergy and Infectious Diseases (NIAID)
NCT06613685	Phase 2/Phase 3 (Phase 3)	Oct 21, 2024	Gilead Sciences
NCT06630286	Phase 3	Oct 9, 2024	Gilead Sciences
NCT06513312	Phase 2	Oct 7, 2024	Gilead Sciences
NCT06338826	Phase 2	Oct 1, 2024	Assistance Publique - Hôpitaux de Paris, Government of France
NCT06719310	Phase 1/Phase 2 (Phase 2)	Aug 28, 2024	Capital Medical University, Jiangsu Aidea Pharmaceutical Co., Ltd
NCT06337032	Phase 4	Aug 27, 2024	Gilead Sciences
NCT06544733	Phase 2/Phase 3 (Phase 3)	Aug 20, 2024	Gilead Sciences
NCT06139796	Phase 1/Phase 2 (Phase 2)	Jun 30, 2024	AMS-PHPT Research Collaboration, Baylor University, Institut National de la Santé Et de la Recherche Médicale, France, PENTA Foundation, University of Zimbabwe

Showing 20 of 521 trials

Page 1 / 27

Organizations

Research & Development (370)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Gilead Sciences	For profit	158	83	5	1999
National Institute of Allergy and Infectious Diseases (NIAID)	Government	71	31	5	2000
Merck	For profit	47	15	5	2007
ViiV Healthcare	For profit	24	14	4	2010
AIDS Clinical Trials Group	Academic/Hospital	22	20	4	2003
Johns Hopkins University	Academic/Hospital	22	7	5	2002
French National Agency for Research on AIDS and Viral Hepatitis	Government	20	20	3	1999
Janssen Pharmaceutica NV	For profit	20	7	5	2009
University of Barcelona	Academic/Hospital	20	16	3	2007
University of North Carolina at Chapel Hill	Academic/Hospital	18	8	5	2003
Bristol-Myers Squibb	For profit	16	6	3	1999
National Institutes of Health (NIH)	Government	15	1	5	2001
University of Washington	Academic/Hospital	14	8	4	2002
Johnson and Johnson	For profit	13	10	4	2010
GlaxoSmithKline	For profit	12	2	3	2005
Harvard University	Academic/Hospital	12	4	3	2005
Emory University	Academic/Hospital	10	7	4	2009
University of California, San Francisco	Academic/Hospital	10	6	3	2007
University of New South Wales	Academic/Hospital	9	9	3	2005
University of Paris	Academic/Hospital	9	0	3	2006

370 organizations

Page 1 / 19

Marketing (35)

Organization	Org type	Relationship	Date
Amneal Pharmaceuticals	For profit	MKTG	Aug 22, 2018
Apotex	For profit	MKTG	Jun 16, 2021
Aurobindo Pharma	For profit	MKTG	Mar 23, 2018
Aurobindo Pharma	For profit	SYN	Jan 26, 2018
Aurobindo Pharma	For profit	NDA2	May 26, 2023
Burroughs Wellcome	For profit	IND	Jan 1, 1994
Chartwell Pharmaceuticals	For profit	MKTG	Jun 4, 2021
Cipla	For profit	MKTG	Jul 2, 2018
Cipla	For profit	SYN	Feb 27, 2012
Cipla	For profit	SYN	Feb 26, 2014
Gilead Sciences	For profit	MKTG	Jul 12, 2006
Gilead Sciences	For profit	SYN	Aug 10, 2011
Gilead Sciences	For profit	NDA	Jul 2, 2003
Hetero Labs Ltd	For profit	MKTG	Oct 31, 2013
Hetero Labs Ltd	For profit	SYN	Dec 22, 2011
Hetero Labs Ltd	For profit	MKTG	Oct 7, 2021
Johnson and Johnson	For profit	MKTG	Jul 17, 2018
Johnson and Johnson	For profit	NDA2	Jul 17, 2018
Laurus Labs Ltd	For profit	MKTG	Jul 26, 2019
Laurus Labs Ltd	For profit	MKTG	Jul 26, 2019
Lupin	For profit	MKTG	Jun 4, 2021
Lupin	For profit	NDA2	Jul 18, 2023
Lupin	For profit	SYN	Dec 13, 2024
Macleods Pharmaceuticals, Ltd	For profit	MKTG	Nov 28, 2014
Matrix Laboratories Limited	For profit	MKTG	Dec 23, 2008
Mylan	For profit	MKTG	Sep 12, 2014
Mylan	For profit	SYN	Nov 20, 2017
Mylan	For profit	SYN	Apr 9, 2018
Mylan	For profit	NDA2	Sep 12, 2014
Neogen	For profit	MKTG	May 15, 2020
PHARMOBEDIENT	For profit	MKTG	Apr 9, 2018
Strides Pharma Science	For profit	MKTG	Jul 31, 2013
Strides Pharma Science	For profit	SYN	Jan 13, 2021
Teva	For profit	MKTG	Jun 8, 2017
Zydus Discovery DMCC	For profit	MKTG	Feb 28, 2020