Terazosin

Routes of
administrationBy mouthATC codeLegal statusLegal status Pharmacokinetic dataProtein binding90–94%Elimination half-life12 hoursIdentifiersCAS NumberPubChem CIDIUPHAR/BPSDrugBankChemSpiderUNIIKEGGChEBIChEMBLCompTox Dashboard (EPA)ECHA InfoCard100.118.191 Chemical and physical dataFormulaC₁₉H₂₅N₅O₄Molar mass387.440 g·mol⁻¹3D model (JSmol)  (verify)

Terazosin, sold under the brand name Hytrin among others, is a medication used to treat symptoms of an enlarged prostate and high blood pressure.^[1] For high blood pressure, it is a less preferred option.^[1] It is taken by mouth.^[1]

Common side effects include dizziness, headache, tiredness, swelling, nausea, and low blood pressure with standing.^[1] Severe side effects may include priapism and low blood pressure.^[1] Prostate cancer should be ruled out before starting treatment.^[1] It is an alpha-1 blocker and works by relaxing blood vessels and the opening of the bladder.^[1]

Terazosin was patented in 1975 and came into medical use in 1985.^[2] It is available as a generic medication.^[3] In 2021, it was the 234th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[4][5]

Synthesis

Reaction of piperazine with 2-furoyl chloride followed by catalytic hydrogenation of the furan ring leads to 2. This, when heated in the presence of 2-chloro-6,7-dimethoxyquinazolin-4-amine (1) undergoes direct alkylation to terazosin (3).

Research

A 2022 study suggests that terazosin may have the potential to confer neuroprotection upon motor neurons in motor neuron disease, as a result of its ability to activate PGK1.^[7]

References