Adefovir
- CAS No.
- 106941-25-7
- Chemical Name:
- Adefovir
- Synonyms
- PMEA;9-[2-(PHOSPHONOMETHOXY)ETHYL]ADENINE;GS-393;gs0393;Adefovi;ADEFOVIR;A Duff Vee;Adefovir98%;Adefovir API;adefovir ,97%
- CBNumber:
- CB2698137
- Molecular Formula:
- C8H12N5O4P
- Molecular Weight:
- 273.19
- MDL Number:
- MFCD00866943
- MOL File:
- 106941-25-7.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| pka | pKa1 2.0, pKa2 6.8(at 25℃) |
| form | powder |
| color | white to beige |
| InChI | 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) |
| InChIKey | SUPKOOSCJHTBAH-UHFFFAOYSA-N |
| SMILES | P(COCCN1C2C(N=C1)=C(N)N=CN=2)(=O)(O)O |
| CAS DataBase Reference | 106941-25-7(CAS DataBase Reference) |
| FDA UNII | 6GQP90I798 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301 | |||||||||
| Precautionary statements | P301+P310 | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 25 | |||||||||
| Safety Statements | 45 | |||||||||
| RIDADR | 2811 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | SZ6563500 | |||||||||
| HazardClass | 6.1 | |||||||||
| PackingGroup | Ⅲ | |||||||||
| HS Code | 29339900 | |||||||||
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
|||||||||
| Hazard Classifications | Acute Tox. 3 Oral | |||||||||
| Hazardous Substances Data | 106941-25-7(Hazardous Substances Data) | |||||||||
| Limited Quantities | 5.0 kg (11 lbs) (solid) | |||||||||
| Excepted Quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) | |||||||||
| NFPA 704 |
|
Adefovir price More Price(66)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML0240 | Adefovir ≥98% (HPLC) | 106941-25-7 | 10mg | $121 | 2026-04-30 | Buy |
| Sigma-Aldrich | SML0240 | Adefovir ≥98% (HPLC) | 106941-25-7 | 50mg | $486 | 2026-04-30 | Buy |
| TCI Chemical | A2322 | Adefovir | 106941-25-7 | 25G | $133 | 2026-04-30 | Buy |
| Cayman Chemical | 18650 | Adefovir ≥95% | 106941-25-7 | 10mg | $36 | 2026-04-30 | Buy |
| Cayman Chemical | 18650 | Adefovir ≥95% | 106941-25-7 | 50mg | $153 | 2026-04-30 | Buy |
Adefovir Chemical Properties, Uses, Production
Description
Adefovir (Trade name: Preveon, Hepsera) is a prescription drug used for the treatment of chronic infections of hepatitis B virus. It can be formulated as the pivoxil prodrug adefovir dipivoxil. However, it shows no effect against HIV-1. As a orally administrated acyclic nucleotide analog reverse transcriptase inhibitor, it blocking the reproduction of HBV through inhibiting the reverse transcriptase in the body. One of its advantages over another anti-HBV drug, lamivudine is that it is much harder for the virus to develop resistance to it.
References
https://www.drugbank.ca/drugs/DB00718
http://en.wikipedia.org/wiki/Adefovir
Chemical Properties
Pale Brown Solid
Uses
Used as an antiviral
Uses
Adefovir has been used to study its anti-retro viral effect on porcine endogenous retrovirus (PERV) activity.
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.
Synthesis
![[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic acid diethyl ester](/CAS/GIF/116384-53-3.gif)
116384-53-3
106941-25-7
The general procedure for the synthesis of ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid from diethyl ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphonate is as follows: a 10L three-necked flask was fitted with a mechanical stirrer and thermometer. 1.4 kg (4.26 mol) of diethyl ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphonate (Intermediate III) and 8 L of acetonitrile were sequentially added to the flask, followed by the addition of trimethylmethylsilyl bromide. The reaction mixture was stirred at room temperature for 1 hour and then heated to reflux for 2 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue, 5 L of water was added, the mixture was stirred and the pH was adjusted to 3.2-3.4 with 25% sodium hydroxide solution. the mixture was heated to reflux for 2 hr. Upon completion of the reaction, the reaction mixture was cooled to room temperature and filtered. The filter cake was purified by aqueous recrystallization and dried under vacuum at 70 °C for 8 h. 9-(2-phosphomethoxyethyl)adenine was obtained as a white crystalline solid powder with a yield of 1.07 kg, 86.3% yield and melting point of 298-300 °C.
References
[1] Nucleosides and Nucleotides, 1998, vol. 17, # 8, p. 1445 - 1451
[2] Patent: CN104387421, 2016, B. Location in patent: Paragraph 0032-0034
[3] Patent: CN106317115, 2017, A. Location in patent: Paragraph 0035; 0036; 0039; 0040; 0046; 0047; 0048
[4] Patent: CN106699814, 2017, A. Location in patent: Paragraph 0024-0025
[5] Green Chemistry, 2012, vol. 14, # 8, p. 2282 - 2288
Adefovir Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Cangzhou Weizhidamei Pharmaceutical Co., Ltd. | 13426038769 | askmryu@163.com | China | 60 | 58 |
| Huangshi Jingchi?Medicine?Co.,?Ltd | 17771967576; 17771967576 | 234107690@qq.com | China | 609 | 58 |
| Shanghai Boyle Chemical Co., Ltd. | 021-50182298 021-50180596 | sales@boylechem.com | China | 2202 | 55 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| future industrial shanghai co., ltd | 400-0066400 13621662912 | sales@jonln.com | China | 1989 | 65 |
| Energy Chemical | 400-0056266 | sales8178@energy-chemical.com | China | 44850 | 61 |
| Capot Chemical Co., Ltd | +86 (0) 571 85 58 67 18 | China | 18187 | 66 | |
| JinYan Chemicals(ShangHai) Co.,Ltd. | 13817811078 | sales@jingyan-chemical.com | China | 9963 | 60 |
| Pure Chemistry Scientific Inc. | 001-857-928-2050 or 1-888-588-9418 | sales@chemreagents.com | United States | 10174 | 62 |
| Adamas Reagent, Ltd. | 400-6009262 15618770481 | yhx@titansci.com | China | 14098 | 59 |
View Latest Price from Adefovir manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-09-17 | Adefovir
106941-25-7
|
1KG | 99%min HPLC | 500kgs | WUHAN FORTUNA CHEMICAL CO., LTD | ||
 |
2026-09-14 | Adefovir
106941-25-7
|
1KG | 99% | 20TONS | Sinoway Industrial co., ltd. | ||
 |
2026-08-20 | Adefovir USP/EP/BP
106941-25-7
|
$1.10 | 1g | 99.9% | 100 Tons Min | Dideu Industries Group Limited |
-
- Adefovir
106941-25-7
- 99%min HPLC
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- Adefovir
106941-25-7
- 99%
- Sinoway Industrial co., ltd.
-
- Adefovir USP/EP/BP
106941-25-7
- $1.10
- 99.9%
- Dideu Industries Group Limited
