Emtricitabine , 98% , 143491-57-0

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

PRODUCT Properties

• Melting point: 136-140°C
• alpha: D25 -133.60° (c = 0.23 in MeOH)
• 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)
• pka: 13.83±0.10(Predicted)
• form: Solid
• color: White to Pale Yellow
• λmax: 280nm(H2O)(lit.)
• Merck: 14,3565
• BCS Class: 1
• InChIKey: XQSPYNMVSIKCOC-NTSWFWBYSA-N

Description and Uses

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.

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Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H302-H315-H319-H335
• Precautionary statements: P261-P305+P351+P338
• RTECS: UW7360500
• HS Code: 2934990002