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HomeProduct name listAdefovir

Adefovir

Synonym(s):GS 0393;GS-393;P-[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic acid, 9-(2-phosphonylmethoxyethyl)adenine;PMEA

  • CAS NO.:106941-25-7
  • Empirical Formula: C8H12N5O4P
  • Molecular Weight: 273.19
  • MDL number: MFCD00866943
  • EINECS: 600-789-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-28 16:48:35
Adefovir Structural

What is Adefovir?

Chemical properties

Pale Brown Solid

The Uses of Adefovir

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

The Uses of Adefovir

Used as an antiviral

What are the applications of Application

Adefovir is an antiviral compound

Definition

ChEBI: Adefovir is a member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection. It has a role as a HIV-1 reverse transcriptase inhibitor, a drug metabolite, an antiviral drug, a nephrotoxic agent and a DNA synthesis inhibitor. It is a member of 6-aminopurines, an ether and a member of phosphonic acids. It is functionally related to an adenine. It is a conjugate acid of an adefovir(1-).

Acquired resistance

It has a lower propensity to induce drug resistance than lamivudine. Clinical trials of patients receiving 48 weeks of therapy did not identify any cases of resistance. Longer courses yield resistant strains of HBV with mutations in the DNA polymerase gene; other rare variants of resistant strains have been identified. Lamivudine-resistant strains of HBV retain susceptibility to adefovir.

Pharmaceutical Applications

A nucleotide analog of adenosine monophosphate, administered orally as its prodrug, adefovir dipivoxil.

Biochem/physiol Actions

Adefovir is an antiviral drug that after intracellular conversion to adefovir diphosphate inhibits hepatitis B virus (HBV) DNA polymerase (reverse transcriptase).

Pharmacokinetics

Oral absorption: c. 60%
Cmax 10 mg/kg oral: 18.4 ng/mL
Plasma half-life: c. 7.5 h.
Volume of distribution: 392 mL/kg
Plasma protein binding: Not known
The prodrug is metabolized to adefovir, which is excreted by the kidneys and therefore requires dose adjustment in patients with impaired renal function. It does not induce cytochrome P450 at standard doses and does not influence the metabolism or plasma concentrations of the other licensed medications used in the treatment of hepatitis B.

Clinical Use

Treatment of chronic hepatitis B virus infection in patients >12 years of age

Side Effects

It is generally well tolerated, with headache, pharyngitis, abdominal pain and peripheral neuropathy being the most common side effects. Nephrotoxicity has been observed in some patients, with those receiving higher doses and longer courses of therapy at greater risk. Exacerbation of hepatitis has been reported in patients immediately following discontinuation of treatment. Most exacerbations occur within 12 weeks of stopping therapy, and elevations of alanine aminotransferase (ALT) up to 10 times the upper limit of normal can be observed in over 25% of patients. Lactic acidosis has been reported in a few patients and is an indication for immediate discontinuation.

Properties of Adefovir

Melting point: >260°C
Boiling point: 632.5±65.0 °C(Predicted)
Density  1.88
storage temp.  -20°C
solubility  0.1 M NaOH: ≥5mg/mL
form  powder
pka pKa1 2.0, pKa2 6.8(at 25℃)
color  white to beige
CAS DataBase Reference 106941-25-7(CAS DataBase Reference)

Safety information for Adefovir

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
Precautionary Statement Codes P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

Computed Descriptors for Adefovir

InChIKey SUPKOOSCJHTBAH-UHFFFAOYSA-N

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