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-WDSKDSINSA-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 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
| 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 |
|---|---|---|
| Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. | 1992 Nov |
|
| Five new drugs enter the homestretch. | 2002 Dec |
|
| 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 |
|
| Treatment of chronic hepatitis B in 2002. | 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 |
|
| Anti-HIV drug updates--three drugs on the near horizon. | 2003 Jan |
|
| Gateways to clinical trials. | 2003 Jan-Feb |
|
| Gateways to clinical trials. | 2003 Jul-Aug |
|
| Gateways to clinical trials. | 2003 Jun |
|
| Gateways to clinical trials. March 2003. | 2003 Mar |
|
| New antiretroviral drugs. | 2003 Mar |
|
| Relative anti-HIV-1 efficacy of lamivudine and emtricitabine in vitro is dependent on cell type. | 2003 Mar 1 |
|
| Once-a-day highly active antiretroviral therapy: a systematic review. | 2003 May 1 |
|
| Atazanavir (Reyataz) and emtricitabine (Emtriva) for HIV infection. | 2003 Nov 10 |
|
| 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 |
|
| FDA notifications. NRTI Emtriva receives FDA approval. | 2003 Oct |
|
| Gateways to clinical trials. | 2003 Oct |
|
| Assessment of the relative potency of emtricitabine and lamivudine. | 2003 Oct 1 |
|
| Emtricitabine: a new treatment option for simplified antiretroviral therapy. | 2003 Sep |
|
| Emtriva gets approval. | 2003 Sep |
|
| New treatment of chronic hepatitis B. | 2004 |
|
| Emtricitabine/tenofovir disoproxil fumarate. | 2004 |
|
| Labeling changes for tenofovir. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 19:17:39 GMT 2023
by
admin
on
Sat Dec 16 19:17:39 GMT 2023
|
| Record UNII |
EV5GXM29XL
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
EV5GXM29XL
Created by
admin on Sat Dec 16 19:17:39 GMT 2023 , Edited by admin on Sat Dec 16 19:17:39 GMT 2023
|
PRIMARY | |||
|
145416-34-8
Created by
admin on Sat Dec 16 19:17:39 GMT 2023 , Edited by admin on Sat Dec 16 19:17:39 GMT 2023
|
PRIMARY | |||
|
22858382
Created by
admin on Sat Dec 16 19:17:39 GMT 2023 , Edited by admin on Sat Dec 16 19:17:39 GMT 2023
|
PRIMARY |