EMTRICITABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H10FN3O3S
Molecular Weight	247.247
Optical Activity	( - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XQSPYNMVSIKCOC-NTSWFWBYSA-N

InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C8H10FN3O3S
Molecular Weight	247.247
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf
Curator's Comment: Description was created based on several sources, including: http://www.emory.edu/news/Releases/emtri/

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	Inhibitor 8504		0.31 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	Primary		Approved 8583	EMTRIVA Approved Use EMTRIVA is indicated, in combination with other antiretroviral agents, for the treatment of HIV-1 infection. Additional important information regarding the use of EMTRIVA for the treatment of HIV-1 Infection: • EMTRIVA should not be coadministered with ATRIPLA™, TRUVADA®, or Lamivudine-containing products (see WARNINGS). • In treatment-experienced patients, the use of EMTRIVA should be guided by laboratory testing and treatment history (see MICROBIOLOGY). Launch Date 2003

C_max

Value	Dose	Co-administered	Analyte	Population
1.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.7 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	5.6 mg/kg 1 times / day steady-state, oral dose: 5.6 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
10 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
12.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	5.6 mg/kg 1 times / day steady-state, oral dose: 5.6 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	5.6 mg/kg 1 times / day steady-state, oral dose: 5.6 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
96% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/	unhealthy, 26 - 42 years Health Status: unhealthy Age Group: 26 - 42 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (grade 2-5, 8 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/

AEs

AE	Significance	Dose	Population
Headache	grade 2-5, 8 patients Disc. AE	200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/	unhealthy, 26 - 42 years Health Status: unhealthy Age Group: 26 - 42 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C19 2057 CYP2E1 1060 CYP3A4/5 296 UGT 45	MATE1 182 OCT1 393 OCT2 434 P-gp 2052 BCRP 697 MRP2 252

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
UGT 70	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21500_emtriva_lbl.pdf#page=5 Page: 5.0	no

Drug as victim

Target	Modality	Activity
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
MATE1 182	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31536	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31536
ChemicalBook	CB5266199	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5266199
eMolecules	6719178	https://www.emolecules.com/cgi-bin/more?vid=6719178
MolPort	MolPort-003-986-424	https://www.molport.com/shop/molecule-link/MolPort-003-986-424
ZINC	ZINC000003629271	http://zinc15.docking.org/substances/ZINC000003629271

PubMed

Title	Date	PubMed
The anti-hepatitis B virus activities, cytotoxicities, and anabolic profiles of the (-) and (+) enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine.	1992 Dec	1336341
Perspectives for the treatment of hepatitis B virus infections.	1999 Jul	10418752
Phenylpropenamide derivatives as inhibitors of hepatitis B virus replication.	2000 Dec 4	11128652
Effect of oral administration of emtricitabine on woodchuck hepatitis virus replication in chronically infected woodchucks.	2000 Jun	10817750
Antiviral drugs: current state of the art.	2001 Aug	11418355
New developments in anti-HIV chemotherapy.	2001 Jan-Feb	11347962
Treatment of chronic hepatitis B.	2001 Nov	11871510
Highlights in the development of new antiviral agents.	2002 Apr	12370077
Treatment of chronic hepatitis B: case selection and duration of therapy.	2002 Apr	11982721
Five new drugs enter the homestretch.	2002 Dec	12635598
Management of viral hepatitis B.	2002 Feb	12000599
Dose range study of pharmacokinetics, safety, and preliminary antiviral activity of emtricitabine in adults with hepatitis B virus infection.	2002 Jun	12019083
Gateways to clinical trials.	2002 Nov	12616707
Therapy of chronic hepatitis B: current challenges and opportunities.	2002 Nov	12431200
Entecavir, FTC, L-FMAU, LdT and others.	2003	14708692
Treatment of chronic hepatitis B in 2002.	2003	12839213
Treatment of chronic hepatitis B in the human immunodeficiency virus-infected patient: present and future.	2003 Dec 15	14689351
Anti-HIV drug updates--three drugs on the near horizon.	2003 Jan	12647672
In vitro activity of potential anti-poxvirus agents.	2003 Jan	12615301
Reproductive toxicology profile of emtricitabine in mice and rabbits.	2003 Jan-Feb	12507664
Gateways to clinical trials.	2003 Jul-Aug	12949633
Gateways to clinical trials.	2003 Jun	12851663
Gateways to clinical trials. March 2003.	2003 Mar	12731460
Atazanavir (Reyataz) and emtricitabine (Emtriva) for HIV infection.	2003 Nov 10	14603099
Three new drugs approved by FDA.	2003 Nov-Dec	14696579
FTC (emtricitabine, Emtriva).	2003 Oct	14696567
New treatment of chronic hepatitis B.	2004	15192805
Emtricitabine/tenofovir disoproxil fumarate.	2004	15139777
[Approval of a new nucleoside. Component of complete once daily regimen].	2004 Apr 26	15373067
[Improved long-term success. New nucleoside for once daily combinations].	2004 Apr 26	15373043
[Recent progress in anti-HIM-1 research].	2004 Jun	15449905
Gateways to clinical trials.	2004 Jun	15319815
Antiviral drugs in current clinical use.	2004 Jun	15125867
Emtricitabine: a once-daily nucleoside reverse transcriptase inhibitor.	2004 Jun	15121999
Antiretrovirals, Part II: focus on non-protease inhibitor antiretrovirals (NRTIs, NNRTIs, and fusion inhibitors).	2004 Nov-Dec	15546830
Resistance issues with new nucleoside/nucleotide backbone options.	2004 Sep 1	15319668
The pipeline: three to watch.	2004 Summer	15386838

Patents

Sample Use Guides

In Vivo Use Guide

Emtriva® (emtricitabine) dosage. Adult Patients (18 years of age and older):one 200 mg capsule administered once daily orally (Capsules). 240 mg (24 mL) administered once daily orally (Oral Solution). Pediatric Patients (0–3 months of age): 3 mg/kg administered once daily orally (Oral Solution). Pediatric Patients (3 months through 17 years): 6 mg/kg up to a maximum of 240 mg (24 mL) administered once daily orally (Oral Solution), for children weighing more than 33 kg who can swallow an intact capsule, one 200 mg capsule administered once daily orally (Capsules).

Route of Administration: Oral

In Vitro Use Guide

emtricitabine EC50 0.99 μM (in vitro activity against HIV-2)

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:09 GMT 2025`
Record UNII	G70B4ETF4S
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ATRIPLA COMPONENT EMTRICITABINE

Preferred Name

English

EMTRICITABINE

Official Name

English

524W91

Code

English

EMTRICITABINE, (-)-

Common Name

English

STRIBILD COMPONENT EMTRICITABINE

Brand Name

English

EVIPLERA COMPONENT EMTRICITABINE

Brand Name

English

DESCOVY COMPONENT EMTRICITABINE

Common Name

English

5-FLUORO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)CYTOSINE (2R,5S)

Common Name

English

EMTRICITABINE [USP-RS]

Common Name

English

TRUVADA COMPONENT EMTRICITABINE

Brand Name

English

2(1H)-PYRIMIDINONE, 4-AMINO-5-FLUORO-1-((2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-

Systematic Name

English

EMTRIVA

Brand Name

English

(-)-EMTRICITABINE

Common Name

English

FTC

Common Name

English

ODEFSEY COMPONENT EMTRICITABINE

Brand Name

English

EMTRICITABINE [MART.]

Common Name

English

COVIRACIL

Brand Name

English

EMTRICITABINE [MI]

Common Name

English

Emtricitabine [WHO-DD]

Common Name

English

EMTRICITABINE [EMA EPAR]

Common Name

English

EMTRICITABINE [VANDF]

Common Name

English

EMTRICITABINE [ORANGE BOOK]

Common Name

English

5-Fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

Systematic Name

English

EMTRICITABINE [JAN]

Common Name

English

524-W-91

Code

English

EMTRICITABINE [HSDB]

Common Name

English

EMTRICITABINE [USAN]

Common Name

English

FTC-(-)

Common Name

English

EMTRICITABINUM [WHO-IP LATIN]

Common Name

English

EMTRICITABINE [WHO-IP]

Common Name

English

(-)-FTC

Common Name

English

BW-524W91

Code

English

emtricitabine [INN]

Common Name

English

(2R-CIS)-4-AMINO-5-FLUORO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-2(1H)-PYRIMIDINONE

Systematic Name

English

Classification Tree Code System Code

WHO-ESSENTIAL MEDICINES LIST

6.4.2.3 (FTC/TEN)