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SML1794

Sigma-Aldrich

Tenofovir disoproxil fumarate

≥98% (HPLC)

Synonym(s):

Bis(POC)PMPA fumarate, Bis{[(Isopropoxycarbonyl)oxy]methyl} ({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)phosphonate fumarate

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About This Item

Empirical Formula (Hill Notation):
C19H30N5O10P · C4H4O4
CAS Number:
202138-50-9
Molecular Weight:
635.51
MDL number:
MFCD08141829
UNSPSC Code:
12352200
PubChem Substance ID:
329826069
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 3 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

OC(/C=C/C(O)=O)=O.NC1=C2C(N(C[C@@H](C)OCP(OCOC(OC(C)C)=O)(OCOC(OC(C)C)=O)=O)C=N2)=NC=N1

InChI

1S/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1

InChI key

VCMJCVGFSROFHV-WZGZYPNHSA-N

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Biochem/physiol Actions

Tenofovir disoproxil fumarate (tenofovir DF) is a nucleotide analogue with activity against retroviruses, such as human immunodeficiency virus (HIV)-1, HIV-2 and hepadnaviruses.
Tenofovir disoproxil fumarate is a prodrug of tenofovir, a nucleotide analogue reverse transcriptase inhibitor (nRTI) that causes premature termination of DNA transcription. In a T cell line and primary blood lymphocytes, the antiviral activity of tenofovir disoproxil was shown to be more than 100-fold greater than tenofovir because of its rapid intracellular uptake. Tenofovir disoproxil fumarate has been used alone and in various combinations for the prevention and treatment of HIV/AIDS and chronic hepatitis B infections and is on the World Health Organization′s List of Essential Medicines.
Tenofovir disoproxil fumarate is a prodrug of tenofovir, a nucleotide analogue reverse transcriptase inhibitor (nRTI); anti-retroviral.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2 - STOT RE 2

target_organs

Bone,Kidney

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tracy P Trang et al.
Expert opinion on drug safety, 15(9), 1287-1294 (2016-07-09)
Tenofovir disoproxil fumarate (TDF) and emtricitabine (FTC) are nucleoside reverse transcriptase inhibitors approved as pre-exposure prophylaxis (PrEP) against human immunodeficiency virus (HIV). Prophylactic TDF-based regimens have been shown to reduce the risk of HIV infection by 74 to 92% among
Tenofovir Disoproxil Fumarate
Kearney B P, et al.
Clinical Pharmacokinetics, 43(9), 595-612 (2004)
Kevin R Robertson et al.
AIDS (London, England), 30(15), 2315-2321 (2016-06-23)
The objective was to determine whether maraviroc (MVC) has unique neurocognitive benefits in the context of initial antiretroviral therapy (ART). Randomized, double-blind, placebo-controlled, 48-week trial. Participants were enrolled in US AIDS Clinical Trials Group clinical trial sites. Total 262 ART-naive
B L Robbins et al.
Antimicrobial agents and chemotherapy, 42(3), 612-617 (1998-03-28)
Bis(isopropyloxymethylcarbonyl) 9-R-(2-phosphonomethoxypropyl)adenine [bis(POC)PMPA] has been identified as a novel prodrug of PMPA. The anti-human immunodeficiency virus activity of bis(POC)PMPA was >100-fold greater than that of PMPA in both an established T-cell line and primary peripheral blood lymphocytes. This improved efficacy
Elisa De Crignis et al.
eLife, 10 (2021-07-31)
The molecular events that drive hepatitis B virus (HBV)-mediated transformation and tumorigenesis have remained largely unclear, due to the absence of a relevant primary model system. Here we propose the use of human liver organoids as a platform for modeling

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