Emtricitabine
Synonym(s):(−)-2′3′-Dideoxy-5-fluoro-3′-thiacytidine;(2R,5S)-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one;FTC
- CAS NO.:143491-57-0
- Empirical Formula: C8H10FN3O3S
- Molecular Weight: 247.25
- MDL number: MFCD00870151
- EINECS: 604-363-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-25 17:59:01
What is Emtricitabine?
Absorption
Emtricitabine reaches a Cmax of 1.8±0.7μg/mL with a Tmax of 1-2 hours, and has an AUC of 10±3.1μg*hr/mL. The bioavailability of emtricitabine capsules is 93% and the bioavailability of the oral solution is 75%. Taking emtricitabine with food decreases the Cmax by 29%.[L9019
Toxicity
The LD50 of emtricitabine is not readily available.[9019,L9818]
Symptoms of emtricitabine toxicity include hepatotoxicity with steatosis, as well as lactic acidosis. Treat overdose with symptomatic and supportive measures, including hemodialysis.
Description
Emtricitabine is a synthetic nucleoside inhibitor of HIV-1 reverse transcriptase. Its mechanism of action entails the phosphorylation of the oxathiolane carbinol function by cellular enzymes to form the corresponding 5′-triphosphate, which competes with the endogenous 2′-deoxycytidine 5′-triphosphate substrate. The in vitro activity of emtricitabine ranges from IC50 of 0.00013 to 0.64 mM against lymphoblastoid cell lines, MAGI-CCR5 cell lines, and peripheral blood mononuclear cells. Emtricitabine is prepared in about 16 steps from L-gulose, from which the O–C–S carbon stereochemistry is derived in the formation of substituted key 4-O-Acetyl-1,3- oxathiolane intermediate. This intermediate is coupled with N-benzoyl-O-trimethylsilyl- 5-fluoro-cytosine in the presence of trimethylsilyl triflate. The resulting anomeric mixture is separated by silica chromatography and subjected to two deprotection steps. Emtricitabine resistant isolates (M184V/I) were cross-resistant to lamivudine (desfluoro version of emtricitabine) and zalcitabine but remained sensitive to abacavir, didanosine, stavudine, tenofovir, zidovudine, and non-nucleoside reverse transcriptase inhibitors (delavirdine, efavirenz, and nevirapine). In a 48-week clinical trial using emtricitabine with didanosine and efavirin versus stavudine, didanosine and efavirenz produced 81 versus 68% responder rate respectively. In one study, 37.5% of treatment na?¨ve patients that were not achieving successful viral levels were found to exhibit a reduced potency toward emtricitabine. This resistance was due to M184V/I mutation in the HIV reverse transcriptase gene. Recommended dosing of emtricitabine is 200 mg (capsule) once per day. It is 93% bio-available and has a plasma half-life about 10 h, with 86% renal clearance. Side effects associated with emtricitabine treatment were generally mild to moderate and included headache, diarrhea, nausea, and rash. A generally mild and asymptomatic hyperpigmentation of the palms and/or soles was also observed.
The Uses of Emtricitabine
Labeled Emtricitabine, intended for use as an internal standard for the quantification of Emtricitabine by GC- or LC-mass spectrometry.
Background
Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) indicated for the treatment of HIV infection in adults or combined with tenofovir alafenamide for the prevention of HIV-1 infection in high risk adolescents and adults. Emtricitabine is a cytidine analogue. The drug works by inhibiting HIV reverse transcriptase, preventing transcription of HIV RNA to DNA.
Emtricitabine was granted FDA approval on 2 July 2003.
Indications
Emtricitabine is indicated in combination with other medications for the treatment of HIV-1 infections; treatment of HIV-1 infections in pediatric patients 25-35kg, treatment of HIV-1 infections in adult patients ≥35kg, for pre exposure prophylaxis of HIV-1 in adolescent and adult patients excluding those who have receptive vaginal sex; treatment of HIV-1 infections in pediatric and adult patients ≥17kg, pre exposure prophylaxis in adolescents and adults ≥35kg; treatment of HIV-1 in patients ≥12 years and ≥35kg; treatment of HIV-1 in patients weighing ≥35kg; treatment of HIV-1 in patients weighing ≥25kg; and treatment of HIV-1 in patients weighing ≥40kg.
What are the applications of Application
Emtricitabine is a HIV-1 reverse transcriptase (HIV-1 RT) inhibitor that can cause termination of DNA chain elongation in viruses.
Pharmacokinetics
Emtricitabine is a cytidine analog that competes with the natural substrate of HIV-1 reverse transcriptase to be incorporated into newly formed DNA, terminating its transcription. It is administered once daily so it has a long duration of action. Patients should be counselled regarding the risk of lactic acidosis and hepatomegaly with steatosis.
Metabolism
Emtricitabine is approximately 86% unmetabolized. Approximately 9% of a dose is metabolized to 3'-sulfoxide diastereomers, 4% to the 2'-O-glucuronide, and a minor amount is converted to 5-fluorocytosine.
Properties of Emtricitabine
Melting point: | 136-140°C |
Boiling point: | 443.3±55.0 °C(Predicted) |
Density | 1.82±0.1 g/cm3(Predicted) |
storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
solubility | Chloroform (Slightly) |
form | Solid |
color | White to Pale Yellow |
Safety information for Emtricitabine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Emtricitabine
InChIKey | XQSPYNMVSIKCOC-NTSWFWBYSA-N |
Abamectin manufacturer
KARPSCHEM LABORATORIES PVT. LTD.
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