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 Date1.057104E12 |
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 Co-administed with:: dolutegravir(50 mg) Sources: tenofovir disoproxil fumarate(300 mg) |
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
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 Co-administed with:: dolutegravir(50 mg) Sources: tenofovir disoproxil fumarate(300 mg) |
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
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 |
---|---|---|
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 |
|
US FDA approves Emtriva (FTC). | 2003 Aug |
|
The continuing evolution of HIV therapy. | 2003 Dec |
|
Selection of a hepatitis B virus strain resistant to adefovir in a liver transplantation patient. | 2003 Dec |
|
Prospective randomized trial of emtricitabine versus lamivudine short-term monotherapy in human immunodeficiency virus-infected patients. | 2003 Dec 1 |
|
Treatment of chronic hepatitis B in the human immunodeficiency virus-infected patient: present and future. | 2003 Dec 15 |
|
FTC (Emtriva) approved. | 2003 Jul 25 |
|
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 |
|
Three new drugs approved by FDA. | 2003 Nov-Dec |
|
FTC (emtricitabine, Emtriva). | 2003 Oct |
|
FDA notifications. NRTI Emtriva receives FDA approval. | 2003 Oct |
|
Gateways to clinical trials. | 2003 Oct |
|
Pharmacokinetics of antiretrovirals in pregnant women. | 2004 |
|
Emtricitabine/tenofovir disoproxil fumarate. | 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 |
|
[Improved long-term success. New nucleoside for once daily combinations]. | 2004 Apr 26 |
|
New once-daily HIV combination better tolerated. | 2004 Dec |
|
Newer treatments for HIV in children. | 2004 Feb |
|
Labeling changes for tenofovir. | 2004 Jan |
|
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 |
|
[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 |
|
Editorial comment: HIV and HBV coinfection--a coming-of-age in treatment strategies. | 2004 Mar |
|
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 |
|
Initial therapy for human immunodeficiency virus: broadening the options. | 2004 Mar-Apr |
|
New drugs of 2003. | 2004 Mar-Apr |
|
Gateways to clinical trials. | 2004 May |
|
Emtricitabine (FTC) for the treatment of HIV infection. | 2004 May |
|
[New approaches in the treatment of hepatitis B]. | 2004 May 21 |
|
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 |
|
A randomized study of emtricitabine and lamivudine in stably suppressed patients with HIV. | 2004 Nov 19 |
|
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 |
|
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 |
|
Pharmacokinetic properties of nucleoside/nucleotide reverse transcriptase inhibitors. | 2004 Sep 1 |
|
Intracellular pharmacology of emtricitabine and tenofovir. | 2004 Sep 15 |
|
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
by
admin
on
Edited
Wed Jul 05 23:25:09 UTC 2023
by
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on
Wed Jul 05 23:25:09 UTC 2023
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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)
Created by
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.3 (EFV/FTC/TEN)
Created by
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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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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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TRANSPORTER -> 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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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 |
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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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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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