U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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 of EMTRICITABINE

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
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.

Originator

Curator's Comment: Liotta, Schinazi and Choi (Emory University) and licensed to Triangle Pharmaceuticals by Emory University in 1996

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.8 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
10 μg × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
96%
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

Doses

DosePopulationAdverse 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:
unhealthy, 26 - 42 years
Health Status: unhealthy
Age Group: 26 - 42 years
Sex: M+F
Sources:
Disc. AE: Headache...
AEs leading to
discontinuation/dose reduction:
Headache (grade 2-5, 8 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 26 - 42 years
Health Status: unhealthy
Age Group: 26 - 42 years
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
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
Perspectives for the treatment of hepatitis B virus infections.
1999 Jul
Phenylpropenamide derivatives as inhibitors of hepatitis B virus replication.
2000 Dec 4
Effect of oral administration of emtricitabine on woodchuck hepatitis virus replication in chronically infected woodchucks.
2000 Jun
Antiviral drugs: current state of the art.
2001 Aug
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
Treatment of chronic hepatitis B.
2001 Nov
Highlights in the development of new antiviral agents.
2002 Apr
Treatment of chronic hepatitis B: case selection and duration of therapy.
2002 Apr
Five new drugs enter the homestretch.
2002 Dec
Management of viral hepatitis B.
2002 Feb
Dose range study of pharmacokinetics, safety, and preliminary antiviral activity of emtricitabine in adults with hepatitis B virus infection.
2002 Jun
Gateways to clinical trials.
2002 Nov
Therapy of chronic hepatitis B: current challenges and opportunities.
2002 Nov
Entecavir, FTC, L-FMAU, LdT and others.
2003
Treatment of chronic hepatitis B in 2002.
2003
Treatment of chronic hepatitis B in the human immunodeficiency virus-infected patient: present and future.
2003 Dec 15
Anti-HIV drug updates--three drugs on the near horizon.
2003 Jan
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Reproductive toxicology profile of emtricitabine in mice and rabbits.
2003 Jan-Feb
Gateways to clinical trials.
2003 Jul-Aug
Gateways to clinical trials.
2003 Jun
Gateways to clinical trials. March 2003.
2003 Mar
Atazanavir (Reyataz) and emtricitabine (Emtriva) for HIV infection.
2003 Nov 10
Three new drugs approved by FDA.
2003 Nov-Dec
FTC (emtricitabine, Emtriva).
2003 Oct
New treatment of chronic hepatitis B.
2004
Emtricitabine/tenofovir disoproxil fumarate.
2004
[Approval of a new nucleoside. Component of complete once daily regimen].
2004 Apr 26
[Improved long-term success. New nucleoside for once daily combinations].
2004 Apr 26
[Recent progress in anti-HIM-1 research].
2004 Jun
Gateways to clinical trials.
2004 Jun
Antiviral drugs in current clinical use.
2004 Jun
Emtricitabine: a once-daily nucleoside reverse transcriptase inhibitor.
2004 Jun
Antiretrovirals, Part II: focus on non-protease inhibitor antiretrovirals (NRTIs, NNRTIs, and fusion inhibitors).
2004 Nov-Dec
Resistance issues with new nucleoside/nucleotide backbone options.
2004 Sep 1
The pipeline: three to watch.
2004 Summer
Patents

Sample Use Guides

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
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
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
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)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (EFV/FTC/TEN)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EMA ASSESSMENT REPORTS TRUVADA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EMA ASSESSMENT REPORTS EMTRIVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AF09
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-VATC QJ05AR09
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EMA ASSESSMENT REPORTS DESCOVY (AUTHORIZED: HIV INFECTIONS )
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
NCI_THESAURUS C1557
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR18
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
NDF-RT N0000175462
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
FDA ORPHAN DRUG 569716
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
NDF-RT N0000009947
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-VATC QJ05AR06
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EMA ASSESSMENT REPORTS STRIBILD (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EMA ASSESSMENT REPORTS EVIPLERA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
LIVERTOX NBK548261
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-VATC QJ05AR08
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EMA ASSESSMENT REPORTS ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR09
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EMA ASSESSMENT REPORTS GENVOYA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-VATC QJ05AF09
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR06
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR03
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
FDA ORPHAN DRUG 559316
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
NCI_THESAURUS C97452
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
EU-Orphan Drug EU/3/14/1420
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR19
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-VATC QJ05AR03
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR20
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR17
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
WHO-ATC J05AR08
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
Code System Code Type Description
HSDB
7337
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
DRUG BANK
DB00879
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID0040129
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
PUBCHEM
60877
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
SMS_ID
100000091720
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
NCI_THESAURUS
C47509
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
EVMPD
SUB01882MIG
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
INN
7822
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
DAILYMED
G70B4ETF4S
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
MERCK INDEX
m4892
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY Merck Index
MESH
C122114
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
USAN
KK-33
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL885
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
FDA UNII
G70B4ETF4S
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
CHEBI
31536
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EMTRICITABINE
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY Description: White to almost white, crystalline powder. Solubility: Freely soluble in methanol R and water R, practically insoluble in dichloromethane R. Category: Antiretroviral (Nucleoside Reverse Transcriptase Inhibitor). Storage: Emtricitabine should be kept in a tightly closed container. Additional information: Emtricitabine may exhibit polymorphism.
DRUG CENTRAL
1003
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
CAS
143491-57-0
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
RS_ITEM_NUM
1235106
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
LACTMED
Emtricitabine
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
WIKIPEDIA
EMTRICITABINE
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY
RXCUI
276237
Created by admin on Mon Mar 31 18:14:09 GMT 2025 , Edited by admin on Mon Mar 31 18:14:09 GMT 2025
PRIMARY RxNorm
Related Record Type Details
TARGET ORGANISM->INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
IC50
RACEMATE -> ENANTIOMER
ENANTIOMER -> ENANTIOMER
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
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METABOLITE -> PARENT
About 4% of dose
MINOR
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METABOLITE -> PARENT
9% of dose
MAJOR
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METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC