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CAS NO.147127-20-6
| Tenofovir Basic information |
| Antiviral drugs Pharmacokinetics Indications Preparation Adverse effects |
| Product Name: | Tenofovir |
| Synonyms: | 1-(6-aminopurin-9-yl)propan-2-yloxymethylphosphonic acid;D,L-TENOFOVIR;TENOFOVIR;(R)-9-(2-PHOSPHONYLMETHOXYPROPYL)-ADENINE;(R)-9-(2-Phosphonomethoxypropyl)Adenine;Tenofovir(ForResearchOnly);(R)-PMPA;[[(1R)-2(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid |
| CAS: | 147127-20-6 |
| MF: | C9H14N5O4P |
| MW: | 287.21 |
| EINECS: | |
| Product Categories: | Purine;ACTIVE PHARMACEUTICAL INGREDIENTS;Nucleotides and Nucleosides;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Inhibitors |
| Mol File: | 147127-20-6.mol |
|
|
|
| Tenofovir Chemical Properties |
| mp | 276-280°C |
| storage temp. | Store at -20°C |
| Water Solubility | 13.4 mg/mL (25 ºC) |
| CAS DataBase Reference | 147127-20-6(CAS DataBase Reference) |
| Safety Information |
| Tenofovir Usage And Synthesis |
| Antiviral drugs |
Nucleoside antiviral drugs are synthetic nucleotide analogs, its chemical structure is simple, easy to modified and synthesis. It is the fastest growing antiviral drugs, a new series of high efficiency and low toxicity of nucleoside analogues against viral medicine have been used in HIV infection and HBV infection treatment. In view of structure, nucleoside analogs drug can be divided into purine and pyrimidine categories. According to main effect, nucleoside analogs drug can be divided into Anti-reverse transcriptase (RT) virus drugs, anti-hepatitis virus drugs, anti-herpes virus drugs and other anti-viral drugs and so on. Tenofovir is an acyclic nucleoside antiviral reverse transcriptase inhibitor. The active substance is Tenofovir disoproxil, while tenofovir is a prodrug that is used because of its better absorption in the gut. Tenofovir can inhibit viral polymerase through direct competitively combine with natural deoxyribose or by insertion to terminate chain of human DNA. It is the first nucleotide analogs to treat HIV-1 infection that approved by the US Food and Drug Administration (FDA). Tenofovir is a main medicine in AIDS cocktail therapy, researches has shown that it can effectively improve the monkeys` ability on prevention of immunodeficiency virus (similar to the human AIDS virus). The above information is edited by the Chemicalbook YangDongmei. |
| Pharmacokinetics | Tenofovir is hardly absorbed through the gastrointestinal tract, for this reason, prodrug of Tenofovir has been developed by esterification, and then to make tenofovir fumarate ester. Tenofovir ester is water-soluble, can be rapidly absorbed and degraded into the active tenofovir, and then was metabolized to the active Tenofovir disoproxil. Tenofovir will reach the peak of plasma Concentration within 1-2 h after administration. When combined with food service, the bioavailability of Tenofovir can be increased by 40%. Intracellular half-life of Tenofovir disoproxil is about 10 h, it needs dosing everyday. Because Tenofovir is not a CYP-450 substrate, this may decrease the possibility of interactions with other drugs caused by CYP450. Elimination of Tenofovir is by glomerular filtration and active tubular secretion. Approximately 70% to 80% is recovered in urine as unchanged drug. Elimination half-life is approximately 17 h. |
| Indications | Tenofovir is indicated for the treatment of HIV, HBV infection. This product also can cooperated with other reverse transcriptase inhibitors for HIV-1 infection and hepatitis B treatment. |
| Preparation | The diethyl phosphite, paraformaldehyde and triethylamine were dissolved in toluene, reacted under nitrogen at reflux. The mixture was cooled after completion, p-toluenesulfonyl chloride and triethylamine was slowly added to afford p-toluenesulfonyloxy methyl phosphonic acid ethyl ester. Under nitrogen, the (S) - glycidyl mixed glycerol, 5% palladium on carbon, ethanol and aqueous sodium hydroxide solution mixture was bubbled with hydrogenated to give (R) -1,2- propanediol. Diethyl carbonate and sodium ethoxide in ethanol solution was stirred to give (R) -1,2- propanediol carbonate. Add this product to adenine, p-toluenesulfonyloxy diethyl methylphosphonate, and sodium hydroxide to dimethylformamide, to gain (R) -9- [2- (diethylphosphono-methoxy-) propyl] adenine. Dissolved it in acetonitrile, add bromotrimethylsilane to give crude Tenofovir, and then recrystallized to get pure product. Add Tenofovir and 1-methyl-2-pyrrolidone, triethylamine to carbonate chloromethyl propyl ester, acidfied by fumaric acid will give Tenofovir fumarate double pivaloyloxy methyl ester. |
| Adverse effects |
1.The most common side effects associated with Tenofovir include asthenia. 2.Tenofovir has also been implicated in mild to moderate gastrointestinal reactions such as nausea, vomiting, diarrhea, and asthenia. Less frequent side effects include hepatotoxicity, abdominal pain, and flatulenceļ¼bloating, lactic acidosis, hepatomegaly with fatty liver, pancreatitis and so on. these adverse effects are common with the use of nucleoside analogues either separately or when combined with other drugs. 3.Tenofovir can also lead to metabolic system hypophosphatemia (1% incidence); fat accumulation and redistribution, including central obesity, buffalo hump, peripheral wasting, breast enlargement, Cushing syndrome. 4.Tenofovir may cause lactic acidosis, hepatomegaly with steatosis-related and so on. 5.Tenofovir may make nervous system: dizziness, headache. 6.Tenofovir sometimes leads to respiratory system: dyspnea. 7.Tenofovir may cause skin herpes. |
| Chemical Properties | White Crystalline Solid |
| Usage | Acyclic phosphonate nucleotide analogue. Used as an anti-HIV agent |
| Usage | Acyclic phosphonate nucleotide analogue; reverse transcriptase inhibitor. Used as an anti-HIV agent. Antiviral. |
| Usage | Tenofovir blocks reverse transcriptase and hepatitis B virus infections. |
| Biological Activity | Selectively inhibits HIV reverse transcriptase (RNA-dependent DNA polymerase). Prevents cytotoxicity in SIV-infected C-8166 cells in vitro (IC 50 = 1.5 μ M). Antiviral agent. |
| Tenofovir Preparation Products And Raw materials |
| Tenofovir Basic information |
| Antiviral drugs Pharmacokinetics Indications Preparation Adverse effects |
| Product Name: | Tenofovir |
| Synonyms: | 1-(6-aminopurin-9-yl)propan-2-yloxymethylphosphonic acid;D,L-TENOFOVIR;TENOFOVIR;(R)-9-(2-PHOSPHONYLMETHOXYPROPYL)-ADENINE;(R)-9-(2-Phosphonomethoxypropyl)Adenine;Tenofovir(ForResearchOnly);(R)-PMPA;[[(1R)-2(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid |
| CAS: | 147127-20-6 |
| MF: | C9H14N5O4P |
| MW: | 287.21 |
| EINECS: | |
| Product Categories: | Purine;ACTIVE PHARMACEUTICAL INGREDIENTS;Nucleotides and Nucleosides;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Inhibitors |
| Mol File: | 147127-20-6.mol |
|
|
|
| Tenofovir Chemical Properties |
| mp | 276-280°C |
| storage temp. | Store at -20°C |
| Water Solubility | 13.4 mg/mL (25 ºC) |
| CAS DataBase Reference | 147127-20-6(CAS DataBase Reference) |
| Safety Information |
| Tenofovir Usage And Synthesis |
| Antiviral drugs |
Nucleoside antiviral drugs are synthetic nucleotide analogs, its chemical structure is simple, easy to modified and synthesis. It is the fastest growing antiviral drugs, a new series of high efficiency and low toxicity of nucleoside analogues against viral medicine have been used in HIV infection and HBV infection treatment. In view of structure, nucleoside analogs drug can be divided into purine and pyrimidine categories. According to main effect, nucleoside analogs drug can be divided into Anti-reverse transcriptase (RT) virus drugs, anti-hepatitis virus drugs, anti-herpes virus drugs and other anti-viral drugs and so on. Tenofovir is an acyclic nucleoside antiviral reverse transcriptase inhibitor. The active substance is Tenofovir disoproxil, while tenofovir is a prodrug that is used because of its better absorption in the gut. Tenofovir can inhibit viral polymerase through direct competitively combine with natural deoxyribose or by insertion to terminate chain of human DNA. It is the first nucleotide analogs to treat HIV-1 infection that approved by the US Food and Drug Administration (FDA). Tenofovir is a main medicine in AIDS cocktail therapy, researches has shown that it can effectively improve the monkeys` ability on prevention of immunodeficiency virus (similar to the human AIDS virus). The above information is edited by the Chemicalbook YangDongmei. |
| Pharmacokinetics | Tenofovir is hardly absorbed through the gastrointestinal tract, for this reason, prodrug of Tenofovir has been developed by esterification, and then to make tenofovir fumarate ester. Tenofovir ester is water-soluble, can be rapidly absorbed and degraded into the active tenofovir, and then was metabolized to the active Tenofovir disoproxil. Tenofovir will reach the peak of plasma Concentration within 1-2 h after administration. When combined with food service, the bioavailability of Tenofovir can be increased by 40%. Intracellular half-life of Tenofovir disoproxil is about 10 h, it needs dosing everyday. Because Tenofovir is not a CYP-450 substrate, this may decrease the possibility of interactions with other drugs caused by CYP450. Elimination of Tenofovir is by glomerular filtration and active tubular secretion. Approximately 70% to 80% is recovered in urine as unchanged drug. Elimination half-life is approximately 17 h. |
| Indications | Tenofovir is indicated for the treatment of HIV, HBV infection. This product also can cooperated with other reverse transcriptase inhibitors for HIV-1 infection and hepatitis B treatment. |
| Preparation | The diethyl phosphite, paraformaldehyde and triethylamine were dissolved in toluene, reacted under nitrogen at reflux. The mixture was cooled after completion, p-toluenesulfonyl chloride and triethylamine was slowly added to afford p-toluenesulfonyloxy methyl phosphonic acid ethyl ester. Under nitrogen, the (S) - glycidyl mixed glycerol, 5% palladium on carbon, ethanol and aqueous sodium hydroxide solution mixture was bubbled with hydrogenated to give (R) -1,2- propanediol. Diethyl carbonate and sodium ethoxide in ethanol solution was stirred to give (R) -1,2- propanediol carbonate. Add this product to adenine, p-toluenesulfonyloxy diethyl methylphosphonate, and sodium hydroxide to dimethylformamide, to gain (R) -9- [2- (diethylphosphono-methoxy-) propyl] adenine. Dissolved it in acetonitrile, add bromotrimethylsilane to give crude Tenofovir, and then recrystallized to get pure product. Add Tenofovir and 1-methyl-2-pyrrolidone, triethylamine to carbonate chloromethyl propyl ester, acidfied by fumaric acid will give Tenofovir fumarate double pivaloyloxy methyl ester. |
| Adverse effects |
1.The most common side effects associated with Tenofovir include asthenia. 2.Tenofovir has also been implicated in mild to moderate gastrointestinal reactions such as nausea, vomiting, diarrhea, and asthenia. Less frequent side effects include hepatotoxicity, abdominal pain, and flatulenceļ¼bloating, lactic acidosis, hepatomegaly with fatty liver, pancreatitis and so on. these adverse effects are common with the use of nucleoside analogues either separately or when combined with other drugs. 3.Tenofovir can also lead to metabolic system hypophosphatemia (1% incidence); fat accumulation and redistribution, including central obesity, buffalo hump, peripheral wasting, breast enlargement, Cushing syndrome. 4.Tenofovir may cause lactic acidosis, hepatomegaly with steatosis-related and so on. 5.Tenofovir may make nervous system: dizziness, headache. 6.Tenofovir sometimes leads to respiratory system: dyspnea. 7.Tenofovir may cause skin herpes. |
| Chemical Properties | White Crystalline Solid |
| Usage | Acyclic phosphonate nucleotide analogue. Used as an anti-HIV agent |
| Usage | Acyclic phosphonate nucleotide analogue; reverse transcriptase inhibitor. Used as an anti-HIV agent. Antiviral. |
| Usage | Tenofovir blocks reverse transcriptase and hepatitis B virus infections. |
| Biological Activity | Selectively inhibits HIV reverse transcriptase (RNA-dependent DNA polymerase). Prevents cytotoxicity in SIV-infected C-8166 cells in vitro (IC 50 = 1.5 μ M). Antiviral agent. |
| Tenofovir Preparation Products And Raw materials |