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Tenofovir Disoproxil (C₁₉H₃₀N₅O₁₀P; MW 519.45 g/mol) is a prodrug of the antiviral agent tenofovir.
Structure:
Phosphonate diester modified with two isopropoxycarbonyloxymethyl (POC) groups.
Function:
Converts in vivo to tenofovir via esterase hydrolysis → phosphorylated to active tenofovir diphosphate.
Mechanism:
Inhibits HIV reverse transcriptase and HBV polymerase (chain terminator).
Clinical Use:
Formulated as fumarate salt (TDF) for HIV treatment/prevention (PrEP) and chronic HBV.
Limitation:
Risk of bone/renal toxicity → largely replaced by tenofovir alafenamide (TAF).
Tenofovir disoproxil (C1919H3030N55O1010P; MW 519.45 g/mol) is a prodrug of tenofovir, enhancing oral bioavailability. Here's its chemical profile:
Core Structure:
Adenine analog linked to acyclic phosphonate (tenofovir’s active form).
Prodrug Modifications:
Two isopropoxycarbonyloxymethyl (POC) groups esterify the phosphonate.
Converts to tenofovir in vivo via esterase hydrolysis.
(iPrO-CO-O-CH₂O)₂-PO-adenine analog
Solubility: Lipophilic esters improve intestinal absorption.
Activation: Hydrolyzes to tenofovir → phosphorylated to active tenofovir diphosphate.
Mechanism: Inhibits HIV/HBV reverse transcriptase by chain termination.
Formulations:
Tenofovir disoproxil fumarate (TDF): For HIV (e.g., Truvada®) and HBV.
Tenofovir disoproxil succinate: Alternate salt.
Replaced by TAF: Newer prodrug (tenofovir alafenamide) has reduced kidney/bone toxicity.
Revolutionized HIV pre-exposure prophylaxis (PrEP) and antiviral therapy.
Tenofovir disoproxil (C₁₉H₃₀N₅O₁₀P) is a prodrug of the nucleotide analog tenofovir. Its structure features two isopropoxycarbonyloxymethyl (POC) groups esterifying the phosphonate, enabling oral absorption. In vivo, esterases hydrolyze it to tenofovir, which is then phosphorylated to tenofovir diphosphate—the active form that inhibits viral reverse transcriptase in HIV/HBV. Marketed as tenofovir disoproxil fumarate (TDF), it was pivotal in HIV treatment/PrEP but is now superseded by tenofovir alafenamide (TAF) for improved safety. Molecular weight: 519.45 g/mol.
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