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SML0240

Sigma-Aldrich

Adefovir

≥98% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C8H12N5O4P
Número de CAS:
106941-25-7
Peso molecular:
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

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000364120
0000364120
0000186212
026M4738V
012M4713V

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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
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
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
Gang Huang et al.
Annals of surgery, 261(1), 56-66 (2014-07-30)
A randomized controlled trial was conducted to find out whether antiviral therapy in patients with hepatitis B-related hepatocellular carcinoma (HCC) improves long-term survival after hepatic resection. Despite advances in surgery and in multidisciplinary treatment, there is still no effective adjuvant
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