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Details

Stereochemistry RACEMIC
Molecular Formula C8H10FN3O3S
Molecular Weight 247.2481
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EMTRICITABINE, (+/-)-

SMILES

c1c(c(=N)nc(n1[C@]2([H])CS[C@]([H])(CO)O2)O)F

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 247.2481
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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

Targets

Targets

Conditions

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

1057104000000
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
Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine.
1992 Nov
New antiretroviral agents.
2001 Mar
Highlights in the development of new antiviral agents.
2002 Apr
Five new drugs enter the homestretch.
2002 Dec
Gateways to clinical trials.
2002 Dec
Management of viral hepatitis B.
2002 Feb
Viral pharmacodynamic model for (-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine (emtricitabine) in chronically infected woodchucks.
2002 May
Gateways to clinical trials.
2002 Nov
Therapy of chronic hepatitis B: current challenges and opportunities.
2002 Nov
New anti-HIV agents and targets.
2002 Nov
Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses.
2002 Sep
FTC superiority over d4T in phase III trial.
2002 Sep-Oct
Treatment of HBeAg negative chronic hepatitis B with new drugs (adefovir and others).
2003
Emtricitabine: an antiretroviral agent for HIV infection.
2003
Treatment of chronic hepatitis B in 2002.
2003
Emtricitabine: 524W91, BW524W91, Coviracil, FTC.
2003
US FDA approves Emtriva (FTC).
2003 Aug
Selection of a hepatitis B virus strain resistant to adefovir in a liver transplantation patient.
2003 Dec
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
Gateways to clinical trials.
2003 Jan-Feb
Reproductive toxicology profile of emtricitabine in mice and rabbits.
2003 Jan-Feb
Gateways to clinical trials.
2003 Jul-Aug
New antiretroviral drugs.
2003 Mar
Current and future antiviral agents for chronic hepatitis B.
2003 Mar
Relative anti-HIV-1 efficacy of lamivudine and emtricitabine in vitro is dependent on cell type.
2003 Mar 1
Once-a-day highly active antiretroviral therapy: a systematic review.
2003 May 1
Atazanavir (Reyataz) and emtricitabine (Emtriva) for HIV infection.
2003 Nov 10
Polysaccharide-based chiral phase under polar organic mode of elution in the determination of the enantiomeric purity of emtricitabine an anti-HIV analogue nucleoside.
2003 Nov 24
Gateways to clinical trials.
2003 Oct
Assessment of the relative potency of emtricitabine and lamivudine.
2003 Oct 1
Emtricitabine: a new treatment option for simplified antiretroviral therapy.
2003 Sep
Emtriva gets approval.
2003 Sep
Pharmacokinetics of antiretrovirals in pregnant women.
2004
Biochemical and mechanistic basis for the activity of nucleoside analogue inhibitors of HIV reverse transcriptase.
2004
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
Emtricitabine: a new nucleoside analogue for once-daily antiretroviral therapy.
2004 Jan
Efficacy and safety of emtricitabine vs stavudine in combination therapy in antiretroviral-naive patients: a randomized trial.
2004 Jul 14
Antiviral drugs in current clinical use.
2004 Jun
Emtricitabine: a once-daily nucleoside reverse transcriptase inhibitor.
2004 Jun
Pharmacokinetics of emtricitabine, didanosine and efavirenz administered once-daily for the treatment of HIV-infected adults (pharmacokinetic substudy of the ANRS 091 trial).
2004 Mar
Emtricitabine (FTC) for the treatment of HIV infection.
2004 May
Pharmacokinetic and pharmacodynamic characteristics of emtricitabine support its once daily dosing for the treatment of HIV infection.
2004 Nov
HIV-chemotherapy and -prophylaxis: new drugs, leads and approaches.
2004 Sep
Resistance issues with new nucleoside/nucleotide backbone options.
2004 Sep 1
New nucleoside/nucleotide backbone options: a review of recent studies.
2004 Sep 1
Intracellular pharmacology of emtricitabine and tenofovir.
2004 Sep 15
Patents

Sample Use Guides

Emtriva® (emtricitabine) dosage.
Route of Administration: Oral
emtricitabine EC50 0.99 μM (in vitro activity against HIV-2)
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:36:13 UTC 2021
Edited
by admin
on Fri Jun 25 20:36:13 UTC 2021
Record UNII
ULS8902U4O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EMTRICITABINE, (+/-)-
Common Name English
(+/-)-FTC
Common Name English
PSI-5004
Code English
BIKTARVY COMPONENT EMTRICITABINE
Brand Name English
EMTRICITABINE (-) COMPONENT OF SYMTUZA
Brand Name English
2(1H)-PYRIMIDINONE, 4-AMINO-5-FLUORO-1-((2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-, REL-
Common Name English
RACIVIR
Common Name English
EMTRICITABINE COMPONENT OF BIKTARVY
Brand Name English
SYMTUZA COMPONENT EMTRICITABINE (-)
Brand Name English
FTC, DL-
Common Name English
2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE, DL-
Common Name English
Code System Code Type Description
WIKIPEDIA
Racivir
Created by admin on Fri Jun 25 20:36:13 UTC 2021 , Edited by admin on Fri Jun 25 20:36:13 UTC 2021
PRIMARY
DRUG BANK
DB12753
Created by admin on Fri Jun 25 20:36:13 UTC 2021 , Edited by admin on Fri Jun 25 20:36:13 UTC 2021
PRIMARY
CAS
143491-54-7
Created by admin on Fri Jun 25 20:36:13 UTC 2021 , Edited by admin on Fri Jun 25 20:36:13 UTC 2021
PRIMARY
FDA UNII
ULS8902U4O
Created by admin on Fri Jun 25 20:36:13 UTC 2021 , Edited by admin on Fri Jun 25 20:36:13 UTC 2021
PRIMARY
MESH
C075889
Created by admin on Fri Jun 25 20:36:13 UTC 2021 , Edited by admin on Fri Jun 25 20:36:13 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE