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
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
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 |
DescriptionCurator's Comment: Description was created based on several sources, including:
http://www.emory.edu/news/Releases/emtri/
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
Sources: http://www.emory.edu/news/Releases/emtri/
Curator's Comment: Liotta, Schinazi and Choi (Emory University) and licensed to Triangle Pharmaceuticals by Emory University in 1996
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL247 |
0.31 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EMTRIVA Approved UseEMTRIVA 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 Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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: |
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
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: |
unhealthy, 26 - 42 years Health Status: unhealthy Age Group: 26 - 42 years Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes |
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 |
|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23187937
emtricitabine EC50 0.99 μM (in vitro activity against HIV-2)
Substance Class |
Chemical
Created
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on
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Record UNII |
G70B4ETF4S
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Record Status |
Validated (UNII)
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.3 (FTC/TEN)
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.3 (EFV/FTC/TEN)
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EMA ASSESSMENT REPORTS |
TRUVADA (AUTHORIZED: HIV INFECTIONS)
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EMA ASSESSMENT REPORTS |
EMTRIVA (AUTHORIZED: HIV INFECTIONS)
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WHO-ATC |
J05AF09
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WHO-VATC |
QJ05AR09
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EMA ASSESSMENT REPORTS |
DESCOVY (AUTHORIZED: HIV INFECTIONS )
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NDF-RT |
N0000175459
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NCI_THESAURUS |
C1557
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WHO-ATC |
J05AR18
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NDF-RT |
N0000175462
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NDF-RT |
N0000175459
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FDA ORPHAN DRUG |
569716
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NDF-RT |
N0000009947
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WHO-VATC |
QJ05AR06
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EMA ASSESSMENT REPORTS |
STRIBILD (AUTHORIZED: HIV INFECTIONS)
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EMA ASSESSMENT REPORTS |
EVIPLERA (AUTHORIZED: HIV INFECTIONS)
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LIVERTOX |
NBK548261
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WHO-VATC |
QJ05AR08
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EMA ASSESSMENT REPORTS |
ATRIPLA (AUTHORIZED: HIV INFECTIONS)
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WHO-ATC |
J05AR09
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EMA ASSESSMENT REPORTS |
GENVOYA (AUTHORIZED: HIV INFECTIONS)
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WHO-VATC |
QJ05AF09
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WHO-ATC |
J05AR06
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WHO-ATC |
J05AR03
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FDA ORPHAN DRUG |
559316
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NCI_THESAURUS |
C97452
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EU-Orphan Drug |
EU/3/14/1420
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WHO-ATC |
J05AR19
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WHO-VATC |
QJ05AR03
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WHO-ATC |
J05AR20
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.1
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WHO-ATC |
J05AR17
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NDF-RT |
N0000175459
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WHO-ATC |
J05AR08
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7337
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DB00879
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DTXSID0040129
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60877
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100000091720
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C47509
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SUB01882MIG
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7822
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G70B4ETF4S
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m4892
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C122114
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KK-33
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CHEMBL885
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G70B4ETF4S
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31536
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EMTRICITABINE
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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. | ||
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1003
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143491-57-0
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1235106
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Emtricitabine
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EMTRICITABINE
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276237
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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TARGET ORGANISM->INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
IC50
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RACEMATE -> ENANTIOMER |
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ENANTIOMER -> ENANTIOMER |
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
About 4% of dose
MINOR
URINE
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METABOLITE -> PARENT |
9% of dose
MAJOR
URINE
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METABOLITE ACTIVE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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