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Details

Stereochemistry RACEMIC
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
Co-administed with::
dolutegravir(50 mg)
tenofovir disoproxil fumarate(300 mg)
Sources:
unhealthy, 26 - 42 years
n = 717
Health Status: unhealthy
Condition: HIV-1
Age Group: 26 - 42 years
Sex: M+F
Population Size: 717
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
Co-administed with::
dolutegravir(50 mg)
tenofovir disoproxil fumarate(300 mg)
Sources:
unhealthy, 26 - 42 years
n = 717
Health Status: unhealthy
Condition: HIV-1
Age Group: 26 - 42 years
Sex: M+F
Population Size: 717
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Antiviral L-nucleosides specific for hepatitis B virus infection.
2001 Jan
New antiretroviral agents.
2001 Mar
Treatment of chronic hepatitis B.
2001 Nov
Management of patients with chronic hepatitis B.
2002 Apr
Management of viral hepatitis B.
2002 Feb
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
Entecavir, FTC, L-FMAU, LdT and others.
2003
Emtricitabine: an antiretroviral agent for HIV infection.
2003
Emtricitabine: 524W91, BW524W91, Coviracil, FTC.
2003
US FDA approves Emtriva (FTC).
2003 Aug
Treatment of chronic hepatitis B in the human immunodeficiency virus-infected patient: present and future.
2003 Dec 15
Gateways to clinical trials.
2003 Jul-Aug
Once-a-day highly active antiretroviral therapy: a systematic review.
2003 May 1
Three new drugs approved by FDA.
2003 Nov-Dec
FTC (emtricitabine, Emtriva).
2003 Oct
Emtricitabine/tenofovir disoproxil fumarate.
2004
Biochemical and mechanistic basis for the activity of nucleoside analogue inhibitors of HIV reverse transcriptase.
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
New once-daily HIV combination better tolerated.
2004 Dec
[Recent progress in anti-HIM-1 research].
2004 Jun
New drugs of 2003.
2004 Mar-Apr
Pharmacokinetic and pharmacodynamic characteristics of emtricitabine support its once daily dosing for the treatment of HIV infection.
2004 Nov
Pharmacologic perspectives for once-daily antiretroviral therapy.
2004 Nov
Antiretrovirals, Part II: focus on non-protease inhibitor antiretrovirals (NRTIs, NNRTIs, and fusion inhibitors).
2004 Nov-Dec
Nevirapine and efavirenz elicit different changes in lipid profiles in antiretroviral-therapy-naive patients infected with HIV-1.
2004 Oct
Combinations of adefovir with nucleoside analogs produce additive antiviral effects against hepatitis B virus in vitro.
2004 Oct
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections.
2004 Oct
Intracellular pharmacology of emtricitabine and tenofovir.
2004 Sep 15
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 Sat Dec 16 06:50:02 GMT 2023
Edited
by admin
on Sat Dec 16 06:50:02 GMT 2023
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
2(1H)-PYRIMIDINONE, 4-AMINO-5-FLUORO-1-((2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-, REL-
Common Name English
FTC, DL-
Common Name English
2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE, DL-
Common Name English
Code System Code Type Description
DRUG BANK
DB12753
Created by admin on Sat Dec 16 06:50:02 GMT 2023 , Edited by admin on Sat Dec 16 06:50:02 GMT 2023
PRIMARY
CAS
143491-54-7
Created by admin on Sat Dec 16 06:50:02 GMT 2023 , Edited by admin on Sat Dec 16 06:50:02 GMT 2023
PRIMARY
FDA UNII
ULS8902U4O
Created by admin on Sat Dec 16 06:50:02 GMT 2023 , Edited by admin on Sat Dec 16 06:50:02 GMT 2023
PRIMARY
PUBCHEM
60877
Created by admin on Sat Dec 16 06:50:02 GMT 2023 , Edited by admin on Sat Dec 16 06:50:02 GMT 2023
PRIMARY
MESH
C075889
Created by admin on Sat Dec 16 06:50:02 GMT 2023 , Edited by admin on Sat Dec 16 06:50:02 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE