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SML0240

Sigma-Aldrich

Adefovir

≥98% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C8H12N5O4P
CAS-Nummer:
106941-25-7
Molekulargewicht:
273.19
MDL-Nummer:
MFCD00866943
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329825251
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Lagerbedingungen

desiccated

Farbe

white to beige

Löslichkeit

0.1 M NaOH: ≥5 mg/mL

Lagertemp.

−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)

InChIKey

SUPKOOSCJHTBAH-UHFFFAOYSA-N

Anwendung

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

Biochem./physiol. Wirkung

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).

Leistungsmerkmale und Vorteile

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301

Gefahreneinstufungen

Acute Tox. 3 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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
9-(2-Phosphonylmethoxyethyl) adenine (PMEA) effectively inhibits retrovirus replication in vitro and simian immunodeficiency virus infection in rhesus monkeys.
Balzarini J, et al.
AIDS, 5(1), 21-28 (1991)
Valeria Cento et al.
The Journal of infection, 67(4), 303-312 (2013-06-26)
The identification of novel reverse-transcriptase (RT) drug-resistance mutations is critical in predicting the probability of success to anti-HBV treatment. Furthermore, due to HBV-RT/HBsAg gene-overlap, they can have an impact on HBsAg-detection and quantification. 356 full-length HBV-RT sequences from 197 drug-naive
Jan Balzarini et al.
PLoS pathogens, 9(7), e1003456-e1003456 (2013-08-13)
Human immunodeficiency virus (HIV) infection is often accompanied by infection with other pathogens, in particular herpes simplex virus type 2 (HSV-2). The resulting coinfection is involved in a vicious circle of mutual facilitations. Therefore, an important task is to develop
K C Cundy
Clinical pharmacokinetics, 36(2), 127-143 (1999-03-27)
Cidofovir and adefovir are members of a new class of antiviral compounds. They are acyclic phosphonate analogues of deoxynucleoside monophosphates. Both compounds undergo intracellular activation to form diphosphates that are potent inhibitors of viral DNA polymerases. Cidofovir has broad spectrum
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