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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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About This Item

Empirical Formula (Hill Notation):
C8H10FN3O3S
CAS Number:
143491-57-0
Molecular Weight:
247.25
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

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
Yuanyuan Hu et al.
Acta diabetologica, 57(3), 279-286 (2019-09-20)
To observe the effects of saxagliptin on the expression of mitogen-activated protein kinase 38 (p38MAPK), nephrin and podocin in renal tissue in type 2 diabetic (T2DM) rats, and to explore the possible mechanism of its renal protection. Forty-eight male Sprague-Dawley
R F Schinazi et al.
Antimicrobial agents and chemotherapy, 36(11), 2423-2431 (1992-11-01)
2',3'-Dideoxy-5-fluoro-3'-thiacytidine (FTC) has been shown to be a potent and selective compound against human immunodeficiency virus type 1 in acutely infected primary human lymphocytes. FTC is also active against human immunodeficiency virus type 2, simian immunodeficiency virus, and feline immunodeficiency
K Das et al.
Journal of virology, 75(10), 4771-4779 (2001-04-20)
Success in treating hepatitis B virus (HBV) infection with nucleoside analog drugs like lamivudine is limited by the emergence of drug-resistant viral strains upon prolonged therapy. The predominant lamivudine resistance mutations in HBV-infected patients are Met552IIe and Met552Val (Met552Ile/Val), frequently
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
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