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SML0240

Sigma-Aldrich

Adefovir

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C8H12N5O4P
Numéro CAS:
106941-25-7
Poids moléculaire :
273.19
Numéro MDL:
MFCD00866943
Code UNSPSC :
12352200
ID de substance PubChem :
329825251
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

0.1 M NaOH: ≥5 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

SUPKOOSCJHTBAH-UHFFFAOYSA-N

Application

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

Actions biochimiques/physiologiques

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).

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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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