SML3051

Emtricitabine

≥98% (HPLC)

• Synonym(s): (-)-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
• Empirical Formula (Hill Notation): C₈H₁₀FN₃O₃S
• CAS Number: 143491-57-0
• Molecular Weight: 247.25
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -150 to -125°, c = 0.25 in methanol
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: FC1=CN(C(=O)N=C1N)[C@H]2O[C@H](SC2)CO
• 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

Description

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).

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable