Adefovir

Modify Date: 2024-01-02 09:25:31

Adefovir Structure
Adefovir structure
Common Name Adefovir
CAS Number 106941-25-7 Molecular Weight 273.186
Density 1.9±0.1 g/cm3 Boiling Point 632.5±65.0 °C at 760 mmHg
Molecular Formula C8H12N5O4P Melting Point >260°C
MSDS Chinese USA Flash Point 336.3±34.3 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Adefovir


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].

 Names

Name Adefovir
Synonym More Synonyms

 Adefovir 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
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

 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
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

 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%

 Articles40

More 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)

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

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 Synonyms

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