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SML0240

Sigma-Aldrich

Adefovir

≥98% (HPLC)

Synonym(s):

GS 0393, GS-393, P-[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic acid, 9-(2-phosphonylmethoxyethyl)adenine, PMEA

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About This Item

Empirical Formula (Hill Notation):
C8H12N5O4P
CAS Number:
106941-25-7
Molecular Weight:
273.19
MDL number:
MFCD00866943
UNSPSC Code:
12352200
PubChem Substance ID:
329825251
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

0.1 M NaOH: ≥5 mg/mL

storage temp.

−20°C

SMILES string

Nc1ncnc2n(CCOCP(O)(O)=O)cnc12

InChI

1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)

InChI key

SUPKOOSCJHTBAH-UHFFFAOYSA-N

Application

Adefovir has been used to study its anti-retro viral effect on porcine endogenous retrovirus (PERV) activity.

Biochem/physiol Actions

Adefovir is an antiviral drug that after intracellular conversion to adefovir diphosphate inhibits hepatitis B virus (HBV) DNA polymerase (reverse transcriptase).
Adefovir, also known as 9-(2-phosphonylmethoxyethyl)adenine (PMEA), is an acyclic nucleoside phosphonate. It has a potential to hinder the in vitro replication of several retroviruses such as human immunodeficiency virus (HIV)-1 and HIV-2, simian immunodeficiency virus (SIV), simian AIDS-related virus (SRV), feline immunodeficiency virus (FIV). Thus, Adefovir may be used as a therapeutic for various retrovirus infections including acquired immunodeficiency syndrome (AIDS).

Features and Benefits

This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

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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Bahar Darsazan et al.
Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques, 21(1), 160-170 (2018-05-24)
Adefovir is an antiviral drug that exhibits high hydrophilic properties and negligible bioavailability (less than 12%). It is only applied in the form of the ester prodrug adefovir dipivoxil (ADV). The oral bioavailability of ADV is limited (32% to 45%)
Anders Boyd et al.
Journal of hepatology, 65(4), 683-691 (2016-05-24)
In the presence of highly-potent antivirals, persistence of hepatitis B virus (HBV) is most well-characterized by covalently-closed circular DNA (cccDNA) and total intrahepatic DNA (IH-DNA). We sought to determine how antiviral therapy could affect their levels during human immunodeficiency virus
Treatment of HBeAg negative chronic hepatitis B with new drugs (adefovir and others).
Stephanos J Hadziyannis et al.
Journal of hepatology, 39 Suppl 1, S172-S176 (2004-01-08)
Caroll B Hartline et al.
Antiviral research, 159, 104-112 (2018-10-06)
The search for new compounds with a broad spectrum of antiviral activity is important and requires the evaluation of many compounds against several distinct viruses. Researchers attempting to develop new antiviral therapies for DNA virus infections currently use a variety
Dante A Suffredini et al.
American journal of physiology. Heart and circulatory physiology, 313(5), H946-H958 (2017-09-10)
Although edema toxin (ETx) and lethal toxin (LTx) contribute to
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