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SML1795

Sigma-Aldrich

Tenofovir

≥98% (HPLC)

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Synonym(s):
(R)-9-(2-Phosphonomethoxypropyl)adenine, (R)-PMPA
Empirical Formula (Hill Notation):
C9H14N5O4P
CAS Number:
147127-20-6
Molecular Weight:
287.21
MDL number:
MFCD00943794
PubChem Substance ID:
329826070

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -20 to -26°, c = 0.5 in 1 M HCl

color

white to beige

solubility

H2O: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

OP(CO[C@H](C)CN1C2=NC=NC(N)=C2N=C1)(O)=O

InChI

1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1

InChI key

SGOIRFVFHAKUTI-ZCFIWIBFSA-N

Biochem/physiol Actions

Tenofovir has a low oral bioavailability. Hence, it is available as a prodrug called tenofovir disoproxil fumarate. Once ingested, tenofovir disoproxil fumarate is hydrolyzed to tenofovir and phosphorylated. This is then incorporated into the viral DNA which leads to chain termination. Tenofovir is also effective against hepatitis B virus.
Tenofovir is a nucleotide analogue reverse transcriptase inhibitor (nRTI) that causes premature termination of DNA transcription. Tenofovir is an antiretroviral used for HIV treatment and prevention.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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
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
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

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