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Cas Database |
| Name |
Adefovir |
EINECS | 600-789-7 |
| CAS No. | 106941-25-7 | Density | 1.88 g/cm3 |
| PSA | 146.19000 | LogP | 0.14150 |
| Solubility | N/A | Melting Point |
>260 °C |
| Formula | C8H12N5O4P | Boiling Point | 632.5 °C at 760 mmHg |
| Molecular Weight | 273.188 | Flash Point | 336.3 °C |
| Transport Information | N/A | Appearance | white to off-white powder |
| Safety | 45 | Risk Codes | 25 |
| Molecular Structure |
|
Hazard Symbols | T |
| Synonyms |
((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid;9-(2-Phosphorylmethoxyethyl)adenine;PMEA;Adefovir [USAN:INN];2-(6-aminopurin-9-yl)ethoxymethylphosphonic acid;N-(2-Phophonomethoxyethyl-2,6-diaminopurine);GS 0393;GS 393;9-(2-(Phosphonomethoxy)ethyl)adenine;Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)-;9-[2-Phosphonylmethoxyethyl]adenine;9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA);9-[2-phosphonyl methoxyethyl]adenine;Adefovir dipivox;9-[2-(phosphonomethoxy)ethyl]adenine;[[2-(6-amino-9H-purin-9-yl) ethoxy] methyl] phosphonic acid;9-(2-phosphonyl methoxyethyl)adenine;Adefovir Dipivozil;9-(2-Phosphonylmethoxyethyl)adenine; |
Article Data | 21 |
Adefovir Synthetic route
- 116384-53-3
[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| With trimethylsilyl bromide | 95% |
| Stage #1: [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester With trimethylsilyl bromide In acetonitrile at 20℃; for 3h; Large scale; Stage #2: With sodium hydroxide In water for 2h; Reflux; Large scale; | 86.3% |
| With hydrogen bromide In water at 90℃; for 5h; Temperature; Time; | 86% |
- 142340-94-1
[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water at 140℃; for 0.166667h; Microwave irradiation; Sealed tube; | 95% |
| Multi-step reaction with 2 steps 1: acetonitrile 2: aq. NH3 View Scheme |
- 107021-27-2
Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| With trimethylsilyl iodide; triethylamine carbonate 1) DMF, R.T., 16 h 2) 80 deg C; Yield given. Multistep reaction; |
- 31618-90-3
diethyl (p-toluenesulfonyloxymethane)phosphonate
- 707-99-3
9-(2-hydroxyethyl)adenine
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| With trimethylsilyl bromide; sodium t-butanolate 1.) DMF; Yield given. Multistep reaction; |
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| With ammonium hydroxide Yield given; | |
| With water | 33.0 g |
- 212894-84-3
[2-(5-Amino-6-chloro-pyrimidin-4-ylamino)-ethoxymethyl]-phosphonic acid diethyl ester
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 92 percent / 3 h / 120 °C 2: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C 3: 95 percent / TMSBr View Scheme |
- 185900-69-0
O,O-diethyl((2-(6-chloro-9H-purin-9-yl)ethoxy)methyl)phosphonate
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C 2: 95 percent / TMSBr View Scheme |
- 55343-28-7
9-(2-Hydroxyethyl)-N6-benzoyladenine
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h 2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme |
- 707-99-3
9-(2-hydroxyethyl)adenine
- 106941-25-7
Adefovir
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 81 percent / chlorotrimethylsilane / pyridine 2: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h 3: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme | |
| Multi-step reaction with 2 steps 1: 1) NaH, 2) 0.5 mol l-1 NaOH / 1) DMF, R.T., 48 h, 2) 50 deg C, 6 h 2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme | |
| Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 5 °C / Large scale 1.2: 5 h / 5 °C / Large scale 2.1: trimethylsilyl bromide / acetonitrile / 3 h / 20 °C / Large scale 2.2: 2 h / Reflux; Large scale View Scheme | |
| Multi-step reaction with 2 steps 1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C 2: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C View Scheme | |
| Multi-step reaction with 2 steps 1.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 78 - 82 °C 1.2: 78 - 82 °C 2.1: trimethylsilyl bromide / 80 - 85 °C View Scheme |
| Conditions | Yield |
|---|---|
| In dichloromethane; water; acetone |
Adefovir Chemical Properties
Molecular Structure of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7):
.png)
Molecular Formula: C8H12N5O4P
Molecular Weight: 273.1857
IUPAC Name: 2-(6-Aminopurin-9-yl)ethoxymethylphosphonic acid
Synonyms of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7): Adefovir [USAN:INN] ; ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid ; 9-(2-(Phosphonomethoxy)ethyl)adenine ; Adefovir ; BRN 3561094 ; DRG-0156 ; GS 0393 ; GS 393 ; GS-0393 ; N-(2-Phophonomethoxyethyl-2,6-diaminopurine) ; N-(2-Phosphonylmethoxyethyl)adenine ; PMEA ; Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)- ; UNII-6GQP90I798
CAS NO: 106941-25-7
Classification Code: Anti-Infective Agents ; Anti-Retroviral Agents ; Antiviral ; Antiviral agents ; Enzyme Inhibitors ; Mutation data ; Nucleic Acid Synthesis Inhibitors ; Reverse Transcriptase Inhibitors
Melting point: >260°C
Index of Refraction: 1.768
Molar Refractivity: 60.14 cm3
Molar Volume: 144.9 cm3
Surface Tension: 103.8 dyne/cm
Density: 1.88 g/cm3
Flash Point: 336.3 °C
Enthalpy of Vaporization: 98.29 kJ/mol
Boiling Point: 632.5 °C at 760 mmHg
Vapour Pressure: 7.24E-17 mmHg at 25°C
Adefovir Uses
9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7) can be used for antiviral.
Adefovir Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD | intravenous | > 1gm/kg (1000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996. |
| mouse | LDLo | intraperitoneal | 1600mg/kg (1600mg/kg) | Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996. |
Adefovir Safety Profile
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx and POx.
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