<Suppliers Price>

Adefovir

Names

[ CAS No. ]:
106941-25-7

[ Name ]:
Adefovir

[Synonym ]:
gs0393
((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid
MFCD00866943
PMEA

Biological Activity

[Description]:

Adefovir (GS-0393) is an adenosine monophosphate analog antiviral agent that after intracellular conversion to Adefovir diphosphate inhibits HBV DNA polymerase. Adefovir has an IC50 of 0.7 μM against HBV in the HepG2.2.15 cell line. Adefovir has good antiviral activity against several viruses, including HBV and herpesviruses[1][2][3].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> HBV
Signaling Pathways >> Anti-infection >> Reverse Transcriptase

[Target]

HBV[1][2][3]; DNA polymerase[1][2]


[In Vitro]

Studies to elucidate the mechanism of action of Adefovir against herpesvirus replication reveals that the phosphorylation of Adefovir occurred intracellularly and is carried out by host cellular enzymes. The diphosphorylated derivatives of Adefovir targeted the viral DNA polymerase and also acted as DNA chain terminators. Adenylate kinase is shown to be responsible for the first phosphorylation, which was followed by ADP kinase and creatine kinase, forming Adefovir diphosphate[1].

[In Vivo]

Unaffected by food, Adefovir achieves 60% oral bioavailability. Its half-life is 12-30 hours and Adefovir undergoes renal excretion without significant metabolites. Adefovir does not substantially affect the cytochrome P450 system[3].

[References]

[1]. X.-X.Zhou, et al. 7.11 - Deoxyribonucleic Acid Viruses: Antivirals for Herpesviruses and Hepatitis B Virus. Comprehensive Medicinal Chemistry II. Volume 7, 2007, Pages 295-327.

[2]. Marcellin P, et al. Adefovir dipivoxil for the treatment of hepatitis B e antigen-positive chronic hepatitis B. N Engl J Med. 2003 Feb 27;348(9):808-16.

[3]. Leah A.Burke, et al. 155 - Drugs to Treat Viral Hepatitis. Infectious Diseases. Volume 2, 2017, Pages 1327-1332.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
632.5±65.0 °C at 760 mmHg

[ Melting Point ]:
>260°C

[ Molecular Formula ]:
C8H12N5O4P

[ Molecular Weight ]:
273.186

[ Flash Point ]:
336.3±34.3 °C

[ Exact Mass ]:
273.062683

[ PSA ]:
146.19000

[ LogP ]:
-2.06

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.769

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SZ6563500
CHEMICAL NAME :
Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)-
CAS REGISTRY NUMBER :
106941-25-7
LAST UPDATED :
199712
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C8-H12-N5-O4-P
MOLECULAR WEIGHT :
273.22

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold

MUTATION DATA

TEST SYSTEM :
Insect - Drosophila melanogaster
DOSE/DURATION :
100 ppm
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 311,305,1994

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26

[ RIDADR ]:
UN 2585 8/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
SZ6563500

[ Packaging Group ]:
III

[ Hazard Class ]:
8

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

In vitro evaluation of 9-(2-phosphonylmethoxyethyl)adenine ester analogues, a series of anti-HBV structures with improved plasma stability and liver release.

Arch. Pharm. Res. 37(11) , 1416-25, (2014)

Chronic hepatitis B virus (HBV) infection may lead to liver cirrhosis and hepatocellular carcinoma, but few drugs are available for its treatment. Acyclic nucleoside phosphonates (ANPs) have remarkabl...

Quantitative high-throughput identification of drugs as modulators of human constitutive androstane receptor.

Sci. Rep. 5 , 10405, (2015)

The constitutive androstane receptor (CAR, NR1I3) plays a key role in governing the transcription of numerous hepatic genes that involve xenobiotic metabolism/clearance, energy homeostasis, and cell p...

Surface engineered polymeric nanocarriers mediate the delivery of transferrin-methotrexate conjugates for an improved understanding of brain cancer.

Biochem. Biophys. Res. Commun. 457(3) , 353-7, (2015)

The objective of present study was to enhance permeation of bioactive molecules across blood brain barrier (BBB) through polysorbate 80 coated poly-lactic-co-glycolic acid (PLGA) nanoparticles (NPs) l...


More Articles

Related Compounds