Synonym: (-)-FTC; (-)-2′,3′-Dideoxy-5-fluoro-3′-thiacytidine; (2R-cis)-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; 5-Fluoro-1-(2R,5S)-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; 524W91; BW 1592; BW 524W91; BW-1592; BW-524W91; BW1592; BW524W91; (−)-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 Number: 143491-57-0
Empirical Formula (Hill Notation): C8H10FN3O3S
Molecular Weight: 247.25
Linear Formula: C8H10FN3O3S
Product Type: Chemical
assay |
≥98% (HPLC) |
color |
white to beige |
form |
powder |
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 |
InChI key |
XQSPYNMVSIKCOC-NTSWFWBYSA-N |
optical activity |
[α]/D -150 to -125°, c = 0.25 in methanol |
Quality Level |
100 ![External link](https://krackeler.com/images/sigma/ext-link.gif) |
solubility |
DMSO: 2 mg/mL, clear |
storage temp. |
2-8°C |
Biochem/physiol Actions: |
Emtricitabine ((-)-FTC) is an orally active, non-cytotoxic (>100 μM/PBM, CEM, Vero, MT-4), potent nucleoside reverse transcriptase inhibitor (NRTI) against HIV type 1/2 (HIV-1 IC50/culture = 8 nM/PBM (LAV-1), 9 nM/CEM (LAV-1); HIV-2 IC50/culture = 0.7 nM/PBM (ROD2), 100 nM/CEM (Zy)), hepatitis B, as well as simian and feline immunodeficiency viruses. Emtricitabine is activated via 2′-deoxycytidine kinase-mediated phosphorylation to (-)-FTC-5′-triphosphate that inhibits viral reverse transcriptase in a dCTP-competitive manner (HIV-1 Ki = 2.9 μM). |
Purity |
≥98% (HPLC) |
Storage Temp. |
2-8°C |
UNSPSC |
12352200 |