Adefovir

Base Information

• Chemical Name: Adefovir
• CAS No.: 106941-25-7
• Molecular Formula: C8H12N5O4P
• Molecular Weight: 273.188
• Hs Code.: 29339900
• UNII: 6GQP90I798
• DSSTox Substance ID: DTXSID6046214
• Nikkaji Number: J291.907I
• Wikipedia: Adefovir
• Wikidata: Q353551
• NCI Thesaurus Code: C61526
• RXCUI: 16521
• Metabolomics Workbench ID: 67779
• ChEMBL ID: CHEMBL484
• Mol file: 106941-25-7.mol

Synonyms:9-(2-phosphonomethoxyethyl)adenine;9-(2-phosphonylmethoxyethyl)adenine;9-PMEA;adefovir

Chemical Property of Adefovir

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: >260 °C
• Boiling Point: 632.5 °C at 760 mmHg
• PKA: pKa1 2.0, pKa2 6.8(at 25℃)
• Flash Point: 336.3 °C
• PSA: 146.19000
• Density: 1.88 g/cm³
• LogP: 0.14150
• Storage Temp.: -20°C Freezer
• Solubility.: 0.1 M NaOH: ≥5mg/mL
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 273.06269088
• Heavy Atom Count: 18
• Complexity: 327

Purity/Quality:

99% ^*data from raw suppliers

Adefovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)CCOCP(=O)(O)O)N
• Recent ClinicalTrials: Drug Transporter Interaction Study PHENTRA_2015_KPUK
• Recent NIPH Clinical Trials: Randomized control study for the effectiveness of tenofovir in nucleoside/nucleotide analogue-treated patients with chronic HBV infection
• 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.
• Uses: Used as an antiviral Adefovir has been used to study its anti-retro viral effect on porcine endogenous retrovirus (PERV) activity.
• Clinical Use: Treatment of chronic hepatitis B virus infection in patients >12 years of age

Technology Process of Adefovir

There total 22 articles about Adefovir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester (116384-53-3) → Adefovir (106941-25-7)

Guidance literature:

With trimethylsilyl bromide;

DOI:10.1080/07328319808003479

Reference yield: 95.0%

[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester (142340-94-1) → Adefovir (106941-25-7)

Guidance literature:

With hydrogenchloride; In water; at 140 ℃; for 0.166667h; Microwave irradiation; Sealed tube;

DOI:10.1039/c2gc35547g

Reference yield:

9-(2-Diethoxyphosphonomethoxyethyl)adenine + trimethylsilyl bromide (2857-97-8) → Adefovir (106941-25-7)

Guidance literature:

In dichloromethane; water; acetone;

upstream raw materials:

[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester

Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine

diethyl (p-toluenesulfonyloxymethane)phosphonate

9-(2-hydroxyethyl)adenine

Downstream raw materials:

9-(2-Phosphonylmethoxyethyl)hypoxanthine

adefovir dipivoxyl

2-tert-butoxycarbonylamino-3-phenyl-propionic acid [2-(6-amino-purin-9-yl)-ethoxymethyl]-(2-tert-butoxycarbonylamino-3-phenyl-propionyloxymethoxy)-phosphinoyloxymethyl ester

2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester

Refernces

• 1、 Gutierrez,Prisbe,Rohloff. "Dealkylation of phosphonate esters with chlorotrimethylsilane". . p. 1299 - 1302. Retrieved 2001.
• 2、 Barral, Karine,Weck, Clément,Payrot, Nadine,Roux, Loic,Durafour, Céline,Zoulim, Fabien,Neyts, Johan,Balzarini, Jan,Canard, Bruno,Priet, Stéphane,Alvarez, Karine. "Acyclic nucleoside thiophosphonates as potent inhibitors of HIV and HBV replication". . p. 4281 - 4288. Retrieved 2011.
• 3、 Dang, Qun,Liu, Yan,Erion, Mark D.. "A new regio-defined synthesis of PMEA". . p. 1445 - 1451. Retrieved 1998.
• 4、 -. "Synthetic method of adefovir dipivoxil". Page/Page column 5-8. . Retrieved 2019/09/05.