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SML3051

Sigma-Aldrich

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

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10 MG
€85.50
50 MG
€259.00

About This Item

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

€85.50

Please contact Customer Service for Availability
Request a Bulk Order

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

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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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000402761
0000402760
0000328198
0000328198
0000402761

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L W Frick et al.
Antimicrobial agents and chemotherapy, 37(11), 2285-2292 (1993-11-01)
The pharmacokinetics and metabolism of the potent anti-human immunodeficiency virus and anti-hepatitis B virus compound, (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine (FTC), were investigated in male CD rats. Plasma clearance of 10 mg of FTC per kg of body weight was biexponential in rats
Magdeleine Hung et al.
Communications biology, 2, 469-469 (2019-12-25)
Emtricitabine (FTC) and lamivudine (3TC), containing an oxathiolane ring with unnatural (-)-stereochemistry, are widely used nucleoside reverse transcriptase inhibitors (NRTIs) in anti-HIV therapy. Treatment with FTC or 3TC primarily selects for the HIV-1 RT M184V/I resistance mutations. Here we provide
Koen K A Van Rompay et al.
Journal of virology, 76(12), 6083-6092 (2002-05-22)
Drug-resistant mutants with a methionine-to-valine substitution at position 184 of reverse transcriptase (M184V) emerged within 5 weeks of initiation of therapy in four newborn macaques infected with simian immunodeficiency virus (SIVmac251) and treated with lamivudine (3TC) or emtricitabine [(-)-FTC] (two
Michele B Daly et al.
PloS one, 14(11), e0225146-e0225146 (2019-11-16)
Macaque models of simian or simian/human immunodeficiency virus (SIV or SHIV) infection are critical for the evaluation of antiretroviral (ARV)-based HIV treatment and prevention strategies. However, modelling human oral ARV administration is logistically challenging and fraught by limited adherence. Here
Richard Hazen et al.
Journal of acquired immune deficiency syndromes (1999), 32(3), 255-258 (2003-03-11)
To assess the relative in vitro potency of the antiviral agents emtricitabine (FTC), lamivudine (3TC), and zidovudine (ZDV) in peripheral blood mononuclear cells (PBMCs), monocyte-derived macrophages, and MT-4 cells infected with HIV-1. DESIGN In vitro evaluation of the test compounds
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