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Key Documents

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:
Molecular Weight:
273.19
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Signal Word

Danger

Hazard Statements

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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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
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)
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
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
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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