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Merck
CN

SML3051

Emtricitabine

≥98% (HPLC), nucleoside reverse transcriptase inhibitor, powder

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

Key Documents

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Product Name

Emtricitabine, ≥98% (HPLC)

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

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

Quality Level

100

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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

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
0000446005
0000446005
0000402761
0000402760
0000328198

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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
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
S K Ono et al.
The Journal of clinical investigation, 107(4), 449-455 (2001-02-22)
After receiving lamivudine for 3 years to treat chronic hepatitis B, 67-75% of patients develop B-domain L528M, C-domain M552I, or M552V mutations in the HBV polymerase that render hepatitis B virus (HBV) drug-resistant. The aim of this study was to
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
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
View All Related Papers

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