Terazosin, sold under the brand name Hytrin among others, is a medication used to treat symptoms of an

enlarged prostate Benign prostatic hyperplasia (BPH), also called prostate enlargement, is a noncancerous increase in size of the prostate gland. Symptoms may include frequent urination, trouble starting to urinate, weak stream, inability to urinate, or loss o ...

and

high blood pressure Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high bl ...

. For high blood pressure, it is a less preferred option. It is taken by mouth. Common side effects include dizziness, headache, tiredness, swelling, nausea, and low blood pressure with standing. Severe side effects may include

priapism Priapism is a condition in which a penis remains erect for hours in the absence of stimulation or after stimulation has ended. There are three types: ischemic (low-flow), nonischemic (high-flow), and recurrent ischemic (intermittent). Most cases ...

and

low blood pressure Hypotension is low blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood. Blood pressure is indicated by two numbers, the systolic blood pressure (the top number) and the dia ...

Prostate cancer Prostate cancer is cancer of the prostate. Prostate cancer is the second most common cancerous tumor worldwide and is the fifth leading cause of cancer-related mortality among men. The prostate is a gland in the male reproductive system that sur ...

should be ruled out before starting treatment. It is an

alpha-1 blocker Alpha-1 blockers (also called alpha-adrenergic blocking agents or alpha-1 antagonists) constitute a variety of drugs that block the effect of catecholamines on alpha-1-adrenergic receptors. They are mainly used to treat benign prostatic hyperpla ...

and works by relaxing

blood vessels The blood vessels are the components of the circulatory system that transport blood throughout the human body. These vessels transport blood cells, nutrients, and oxygen to the tissues of the body. They also take waste and carbon dioxide away f ...

and the opening of the

bladder The urinary bladder, or simply bladder, is a hollow organ in humans and other vertebrates that stores urine from the kidneys before disposal by urination. In humans the bladder is a distensible organ that sits on the pelvic floor. Urine enters ...

. Terazosin was patented in 1975 and came into medical use in 1985. It is available as a

generic medication A generic drug is a pharmaceutical drug that contains the same chemical substance as a drug that was originally protected by chemical patents. Generic drugs are allowed for sale after the patents on the original drugs expire. Because the active ch ...

. In 2020, it was the 211th most commonly prescribed medication in the United States, with more than 2million prescriptions. A study by researchers from the University of Edinburgh and the University of Oxford, published in 2022, suggested 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.

Synthesis

Reaction of

piperazine Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad ...

with 2-furoyl chloride followed by

catalytic hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

of the

furan Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly ...

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).

References

{{Adrenergic receptor modulators Alpha-1 blockers Carboxamides Phenol ethers Piperazines Quinazolines Tetrahydrofurans Wikipedia medicine articles ready to translate