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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 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
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| New once-daily HIV combination better tolerated. | 2004-12 |
|
| A randomized study of emtricitabine and lamivudine in stably suppressed patients with HIV. | 2004-11-19 |
|
| Antiretrovirals, Part II: focus on non-protease inhibitor antiretrovirals (NRTIs, NNRTIs, and fusion inhibitors). | 2004-11-18 |
|
| Pharmacokinetic and pharmacodynamic characteristics of emtricitabine support its once daily dosing for the treatment of HIV infection. | 2004-11 |
|
| Pharmacologic perspectives for once-daily antiretroviral therapy. | 2004-11 |
|
| Nevirapine and efavirenz elicit different changes in lipid profiles in antiretroviral-therapy-naive patients infected with HIV-1. | 2004-10 |
|
| Combinations of adefovir with nucleoside analogs produce additive antiviral effects against hepatitis B virus in vitro. | 2004-10 |
|
| New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections. | 2004-10 |
|
| Intracellular pharmacology of emtricitabine and tenofovir. | 2004-09-15 |
|
| Resistance issues with new nucleoside/nucleotide backbone options. | 2004-09-01 |
|
| New nucleoside/nucleotide backbone options: a review of recent studies. | 2004-09-01 |
|
| Pharmacokinetic properties of nucleoside/nucleotide reverse transcriptase inhibitors. | 2004-09-01 |
|
| HIV-chemotherapy and -prophylaxis: new drugs, leads and approaches. | 2004-09 |
|
| Efficacy and safety of emtricitabine vs stavudine in combination therapy in antiretroviral-naive patients: a randomized trial. | 2004-07-14 |
|
| [Recent progress in anti-HIM-1 research]. | 2004-06 |
|
| Gateways to clinical trials. | 2004-06 |
|
| Antiviral drugs in current clinical use. | 2004-06 |
|
| Emtricitabine: a once-daily nucleoside reverse transcriptase inhibitor. | 2004-06 |
|
| [New approaches in the treatment of hepatitis B]. | 2004-05-21 |
|
| Gateways to clinical trials. | 2004-05 |
|
| Emtricitabine (FTC) for the treatment of HIV infection. | 2004-05 |
|
| Initial therapy for human immunodeficiency virus: broadening the options. | 2004-04-30 |
|
| [Approval of a new nucleoside. Component of complete once daily regimen]. | 2004-04-26 |
|
| [Improved long-term success. New nucleoside for once daily combinations]. | 2004-04-26 |
|
| New drugs of 2003. | 2004-04-22 |
|
| Editorial comment: HIV and HBV coinfection--a coming-of-age in treatment strategies. | 2004-03 |
|
| Pharmacokinetics of emtricitabine, didanosine and efavirenz administered once-daily for the treatment of HIV-infected adults (pharmacokinetic substudy of the ANRS 091 trial). | 2004-03 |
|
| Newer treatments for HIV in children. | 2004-02 |
|
| Labeling changes for tenofovir. | 2004-01 |
|
| Emtricitabine: a new nucleoside analogue for once-daily antiretroviral therapy. | 2004-01 |
|
| Pharmacokinetics of antiretrovirals in pregnant women. | 2004 |
|
| The pipeline: three to watch. | 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 |
|
| Three new drugs approved by FDA. | 2003-12-31 |
|
| Treatment of chronic hepatitis B in the human immunodeficiency virus-infected patient: present and future. | 2003-12-15 |
|
| Prospective randomized trial of emtricitabine versus lamivudine short-term monotherapy in human immunodeficiency virus-infected patients. | 2003-12-01 |
|
| The continuing evolution of HIV therapy. | 2003-12 |
|
| Selection of a hepatitis B virus strain resistant to adefovir in a liver transplantation patient. | 2003-12 |
|
| Polysaccharide-based chiral phase under polar organic mode of elution in the determination of the enantiomeric purity of emtricitabine an anti-HIV analogue nucleoside. | 2003-11-24 |
|
| FTC (emtricitabine, Emtriva). | 2003-10 |
|
| FDA notifications. NRTI Emtriva receives FDA approval. | 2003-10 |
|
| Gateways to clinical trials. | 2003-10 |
|
| US FDA approves Emtriva (FTC). | 2003-08 |
|
| FTC (Emtriva) approved. | 2003-07-25 |
|
| 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 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:38:26 GMT 2025
by
admin
on
Mon Mar 31 21:38:26 GMT 2025
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| Record UNII |
ULS8902U4O
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| Record Status |
Validated (UNII)
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| Record Version |
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DB12753
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143491-54-7
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ULS8902U4O
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C075889
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admin on Mon Mar 31 21:38:26 GMT 2025 , Edited by admin on Mon Mar 31 21:38:26 GMT 2025
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ENANTIOMER -> RACEMATE |
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