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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.31 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EMTRIVA

Cmax

ValueDoseCo-administeredAnalytePopulation
1.8 μg/mL
200 mg 1 times / day multiple, oral
EMTRICITABINE plasma
Homo sapiens
2.7 μg/mL
5.6 mg/kg 1 times / day steady-state, oral
EMTRICITABINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
10 μg × h/mL
200 mg 1 times / day multiple, oral
EMTRICITABINE plasma
Homo sapiens
12.6 μg × h/mL
5.6 mg/kg 1 times / day steady-state, oral
EMTRICITABINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
200 mg 1 times / day multiple, oral
EMTRICITABINE plasma
Homo sapiens
8.2 h
5.6 mg/kg 1 times / day steady-state, oral
EMTRICITABINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
96%
200 mg 1 times / day multiple, oral
EMTRICITABINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
ULS8902U4O
Record Status Validated (UNII)
Record Version